meta-scriptThe Rihanna Essentials: 15 Singles To Celebrate The Singer's Endless Pop Reign | GRAMMY.com
The Rihanna Essentials: 15 Singles To Celebrate The Singer's Endless Pop Reign
Rihanna attends the "Black Panther 2: Wakanda Forever" Premiere on Oct. 26, 2022 in Hollywood, Calif.

Photo: Axelle/Bauer-Griffin/FilmMagic

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The Rihanna Essentials: 15 Singles To Celebrate The Singer's Endless Pop Reign

Upon the release of "Lift Me Up" — Rihanna's first solo single in more than six years — GRAMMY.com rounds up 15 tracks that showcase her vocal prowess and bad gal energy.

GRAMMYs/Oct 28, 2022 - 10:04 pm

Over the past five years, Rihanna has built a booming business portfolio — and reported $1.7 billion empire — that includes beauty, skin and lingerie/loungewear companies. Meanwhile, the singer, born Robyn Fenty, left fans eagerly waiting for new music — and the wait is finally over.

"Lift Me Up," Rihanna's first solo single in six years, arrived on Oct. 28, just two days after she erupted the internet with the announcement of her return. The song is the lead single to the also highly anticipated Black Panther: Wakanda Forever soundtrack, and focuses on a universal need for love and tenderness.

With the new song and plans to perform the halftime show at the 2023 Super Bowl, it's natural to wonder what else may be on the way. In the meantime, take a look back at 15 essential singles that showcase RIhanna's growth, versatility and impact on popular music — and get ready for the next Rihanna era.

Listen to all of the songs in GRAMMY.com's Rihanna Essentials Playlist on Spotify, Apple Music, and Amazon Music, powered by GRAMMY U.

"Pon de Replay" (2005)

Rihanna's debut single offers a good-girl twist on dancehall pop as she implores the DJ to rewind her favorite song. According to The Guardian, when she was 16, Rihanna signed a deal with New York City's Syndicated Rhythm Productions (SRP). Founders Carl Sturken and Evan Rogers put the song on a demo with her that attracted the attention of Jay-Z and music executive L.A. Reid. After she auditioned in person, she was signed to Def Jam in a joint deal with SRP.

"Pon de Replay" hit no. 2 on the Billboard Hot 100 within two months of its release — not bad for a first outing!

"Umbrella" (2007)

Her epic collaboration with Jay-Z and producers Tricky Stewart and The-Dream, "Umbrella" consciously traded her good-girl image for something more mature. A song about enduring friendship that lasts a lifetime, "Umbrella" put her onto a new pop music playing field with the forever stars, sitting atop the Hot 100 for 7 weeks and topping charts around the globe. "Umbrella" also earned Rihanna her first GRAMMY, winning the award for Best Rap/Sung Collaboration in 2008.

"Don't Stop The Music" (2007)

The GRAMMY-nominated "Don't Stop The Music" carries on an iconic pop hook, the "mama say mama sa mama coosa" refrain from Manu Dibango's "Soul Makossa" that was popularized in Michael Jackson's 1982 smash "Wanna Be Startin' Somethin'." "Don't Stop The Music" earned RIhanna her fifth No. 1 on Billboard's Dance Club Songs chart (as of press time, she has 33 to date) and signaled that the music was indeed not going to stop for her — and neither were the hits.

"Hard" (2009)

Atlanta rapper Jeezy guest stars on Rihanna's second single from her fourth album, Rated R. An empowerment anthem for herself and others, she set her music and business destiny with the line, "Tougher than a lion, ain't no need in tryin'/ I live where the sky ends, yup, you know this."

"Rude Boy" (2009)

One of Rihanna's many dancehall-inspired singles, "Rude Boy" is her most successful solo chart hit to date, notching five weeks atop the Hot 100. A cheeky poke at silly dating situations and pick-up lines, the fun bravado of "Rude Boy" dares men to see if they're "big enough" for her.

"Love The Way You Lie" (2010)

Eminem recruited Rihanna to collaborate on his relatable song about being trapped in lust with someone who isn't exactly the most truthful, and its message connected with listeners around the world. "Love The Way You Lie" gave Rihanna another No. 1, but more prominently, her first certified Diamond single — and her only to date. As of press time, the song has sold more than 13 million copies.

"Only Girl (in the World)" (2010)

Even 12 years after its release, "Only Girl (in the World)" still has the power to propel dance floors with its insistent beat. The way Rihanna belts out her high-octave chorus remains one of the strongest vocal displays in her catalog. It's also seemingly a critical favorite, as the song was the first solo song to win Rihanna a GRAMMY. (To date, Rihanna has won 9 GRAMMYs and has received 33 nominations overall. All but two of her wins are for collaborations.)

"Man Down" (2010)

Rihanna is all guns blazing on this chillingly murderous reggae single from Loud. Its deadly metaphor for breaking a man's heart is a striking display of Rihanna's confident songwriting, one of two reasons why the song is important to the singer herself. "It's a very cleverly written song, and what I love about it is that it's not a lyric you'd normally hear a female singing," Rihanna told Spin in 2010. "The vibe is Jamaican and West Indian. That's something that's close to me."

"We Found Love" (2011)

With its frenetic electronic beats, relentless treble and big breakdowns, Rihanna captured the EDM zeitgeist with "We Found Love" and earned herself another otherworldly smash hit. It remains her longest-running No. 1 on the Hot 100, topping the chart for 10 weeks in 2011. The heady, pilled-and-thrilled music festival vibe of the music video helped score Rihanna and Calvin Harris a GRAMMY Award for Best Music Video in 2013.

"Diamonds" (2012)

One of Rihanna's all-time calling cards, "Diamonds" was created with the help of Australian artist (and co-writer) Sia and power producers Stargate and Benny Blanco. But it's Rihanna's dynamic vocal performance that makes the song particularly special. "Diamonds" topped charts all over the world, including the Billboard Hot 100.

"Stay" (2012)

Nashville artist Mikky Ekko co-wrote and dueted on the slow burner "Stay," one of Rihanna's more poignant duets. The song's spare instrumentation highlights the vulnerable beauty of her voice and emotive range, a special highlight in a discography laden with layered digital beats and dance-floor anthems. Rihanna and Ekko performed the song live at the 55th GRAMMY Awards in 2013, where it was nominated for Best Pop Duo/Group Performance.

"B— Better Have My Money" (2015)

Rihanna channels the soul of rapper AMG's 1991 gangster rap classic "B— Better Have My Money" into a viral smash. The trap beats touched on the hip-hop inspired sounds of her 2012 album, Unapologetic, further expanding her rather dance-forward discography — and showing that, as she stated in 2009, she goes hard.

"Work" (2016)

Five years after Drake recruited Rihanna for the title track to his 2011 album Take Care, she invited him to collaborate on the lead single for her 2016 LP, Anti — and the reignited partnership proved to be massive. "Work" became Rihanna's 14th No. 1 hit on the Billboard Hot 100, and made her the only artist to have seven consecutive albums score a Hot 100 chart-topper. What's more, it served as another opportunity for the Barbados-born singer to tap into her Caribbean roots — and arguably reinvigorated dancehall as a whole.

"Love On the Brain" (2016)

Rihanna's infatuation-drenched doo-wop ditty is a slow burner, but a wowing performance that puts her voice on display. While Anti cut "Higher" also does that, the polished beauty of "Love On The Brain" made it a perfect final single from the album — and a lovely cliffhanger for Rihanna's musical absence.

"Lift Me Up" (2022)

Rihanna made her triumphant return to music in sophisticated fashion. "Lift Me Up" marks RIhanna's first solo single in six years. The tender track features subtle production, allowing Rihanna's voice to shine, and offering a stunning declaration that she's back. 

As some fans noted on Twitter, "Lift Me Up" shows that Rihanna may be on an even bigger level in this next era. "The maturity in Rihanna's voice whew LORD," one fan reacted. Another echoed, "Six years away from solo material done took her ballading to a new level.

Whatever comes next, one thing remains clear: that Rihanna reign just won't let up.

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Songbook: The Ultimate Guide To Rihanna's Reign, From Her Record-Breaking Hits To Unforgettable Collabs
(L-R) Rihanna in 2023, 2006 and 2010.

Photos: Kevin Mazur/Getty Images for Roc Nation, Greetsia Tent/WireImage, Kevin Mazur/WireImage

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Songbook: The Ultimate Guide To Rihanna's Reign, From Her Record-Breaking Hits To Unforgettable Collabs

As the world eagerly awaits Rihanna's musical comeback, GRAMMY.com takes a deep dive into the superstar's catalog and celebrates her evolution from teen idol to beloved icon.

GRAMMYs/Feb 20, 2024 - 06:37 pm

A chance meeting changed Rihanna's life.

The singer was just 15 years old when she met producer Evan Rogers, who was vacationing with his wife in Barbados. Rogers recognized Rihanna's potential, and invited her to an audition in his hotel suite. 

Shortly after her 16th birthday, Rihanna left her home country for the U.S. to record a demo, which included her breakthrough hit "Pon de Replay." The demo found its way into Jay-Z's hands, and Hov signed the teen artist to Def Jam and the label expedited her 2005 debut album, aptly titled Music of the Sun.

"When I left Barbados, I didn't look back," Rihanna told Entertainment Weekly in 2007. "I wanted to do what I had to do [to succeed], even if it meant moving to America." 

Twenty years later, Rihanna is a renowned entertainer-turned-mogul. She has sold over 40 million albums worldwide, garnered over 12 billion Spotify streams, achieved 14 Billboard Hot 100 chart-toppers, and won nine GRAMMY Awards. Even her business ventures have been a massive success, as her Fenty Beauty brand is worth $2.8 billion.

Though it's been close to a decade since Rihanna's last studio album, 2016's ANTI, she reminded the world of her reign with her 2023 Super Bowl halftime show — which also marked her first time taking the stage in five years. Performing hit after hit while unveiling a baby bump, her 13-minute set became one of the most-watched halftime shows of all time with over 121 million viewers. 

In honor of Rihanna's 36th birthday on Feb. 20, GRAMMY.com is revisiting the monstrous hits, ambitious projects, brow-raising visuals, and iconic collabs that propelled her to international stardom — and why it's all put her in a league of her own.

A New Island Girl In Town

True to her Carribean heritage, Rihanna's dancehall-inspired debut single "Pon de Replay" earned the then 17-year-old Barbados native her first entry on the Hot 100 at an impressive No. 2. Her official introduction to the world also hit No. 1 on the Billboard Dance Club Songs chart; she boasts 33 on the tally, second behind only the Queen of Pop herself, Madonna.

Follow-up single "If It's Lovin' That You Want" stalled at No. 36 on the Hot 100, but still whetted fans' appetite — as did her debut album, Music of the Sun, which is mostly comprised of dance-pop and dancehall tracks with hints of R&B (like "Willing to Wait"). Plus, her reimagining of Dawn Penn's 1994 reggae classic "You Don't Love Me (No, No, No)" is still so fun to listen to after all these years.

A mere eight months later, Rihanna's sophomore effort, 2006's A Girl Like Me, arrived to an eager audience. Defying the sophomore slump, she celebrated her first No. 1 with the ubiquitous lead single "SOS," which famously samples Soft Cell's 1981 hit, "Tainted Love." While A Girl Like Me is filled with high-energy, danceable tracks (including the nostalgic "Break It Off" with Sean Paul), Rihanna's second single was the melodramatic ballad "Unfaithful." 

Penned by then-labelmate Ne-Yo, "Unfaithful" peaked at No. 6 on the Hot 100. More importantly, it showed a different side to Rihanna, proving that she could channel deep emotion when the performance calls for it. It also marked Rihanna's first time veering away from her "girl next door" image, as the song's subject matter deals with infidelity.

A Girl Like Me contains many fan favorites, from the laid-back "We Ride" to standouts "Dem Haters" and "Kisses Don't Lie." The latter is a reggae-rock hybrid that sounds like a catalyst for some of Rihanna's edgier tunes like "Breakin' Dishes" from 2007's Good Girl Gone Bad era. Touching ballads"Final Goodbye" and "A Million Miles Away" showcase her voice beautifully, foreshadowing later big-vocal numbers like "Love on the Brain."

An Icon In The Making

Rihanna was a familiar face by 2007, but with the arrival of her third studio album, Good Girl Gone Bad, she graduated from cookie-cutter pop star to bonafide icon.

Produced by Tricky Stewart, the LP's juggernaut lead single "Umbrella" featuring Jay-Z skyrocketed to No. 1 in 17 countries. Between striking images of Rihanna's silver-painted silhouette in the accompanying video and the now-iconic "ella-ella, eh, eh, eh" hook, "Umbrella" thrust the then 19-year-old into another stratosphere. Her confident delivery also commanded attention in a way fans and critics hadn't heard before.

The transformative era also birthed the gritty "Shut Up and Drive," on which Rihanna channels her inner rock star. The next two singles cracked the top 10: an affectionate duet with Ne-Yo,  "Hate That I Love You," which showed off Rihanna's softer side, and the party-starting, Michael Jackson-sampling "Don't Stop the Music," which cemented her place in the digital era. 

The melancholy "Rehab" is a clever metaphor for lost love, co-written by Timbaland and Justin Timberlake. Despite being Good Girl Gone Bad's lowest-charting single, Timberlake heralded the song as "the bridge for her to be accepted as an adult in the music industry."

Good Girl Gone Bad remains Rihanna's best-selling album and marks her greatest reinvention as she adopted a more rebellious sound. She also won her first GRAMMY in 2008 (Best Rap/Sung Collaboration for "Umbrella") and scored four other nominations, including Record Of The Year. The album's reissue spawned two more No. 1s: "Take a Bow" and "Disturbia," the latter of which acts like a prelude to Rated R, which saw Rihanna exploring darker themes.

Nine months before the release of 2009's Rated R, Rihanna was assaulted by then-boyfriend Chris Brown. On the deeply personal album, she translated her pain into art. Through lead single "Russian Roulette" and bitingly catchy anthems "Stupid in Love," "Fire Bomb," "Photographs," "Cold Case Love," and "The Last Song," Rihanna explored her angst and confusion.

But to focus solely on the domestic violence incident undermines Rihanna's artistic vision. 

Following three multi-platinum albums in a three-year span, Rihanna's rebranding as a rebel at heart reached its apex. The singer had grown in leaps and bounds while taking musical risks, even penning nine of Rated R's 13 tracks (she had no writing credits on Good Girl Gone Bad).

The road to Rihanna's most badass anthems — including "Bitch Better Have My Money" — can be traced back to Rated R. Case in point: Her bravado is loud and clear on "Hard," "Wait Your Turn," and "G4L." On "Rockstar 101," which features legendary rocker Slash, Rihanna declares her power: "Six inch walker/ Big sh— talker/ I never play the victim/ I'd rather be a stalker."

Badgal RiRi returned to her dancehall roots on her fifth No. 1 "Rude Boy," which offsets the album's harrowing motif. Final single "Te Amo" didn't chart, but garnered a great deal of attention as the Latin-infused Stargate production depicts Rihanna being enticed by a female love interest. 

Rated R showcased Rihanna's undeniable star power, and allowed her to shed her good-girl image once and for all.

A Partygoer's Dream

Following the career-pivoting Rated R, 2010's Loud offered a welcome return to the West Indian artist's earlier sound. The album feels like one big celebration of life, as evidenced by Rihanna's fire-engine red hair and No. 1 singles "Only Girl (In the World)" and "What's My Name?" (the latter of which was Rih's first collaboration with Drake).

Best described as "Don't Stop the Music" 2.0, the effervescent "Only Girl" marked her eminent return to the dance floor and took home a GRAMMY for Best Dance Recording in 2011. While "What's My Name?" may not outshine Rih and Drizzy's other collabs — including 2011's "Take Care" or 2016's "Work" — the second she sings, "Hey, boy, I really wanna see if you can go downtown with a girl like me," it's impossible not to whine your waist to the riddim.

Easily one of Rihanna's most overlooked hits, "Cheers (Drink to That)" is built around an unexpected sample of Avril Lavigne's 2002 hit "I'm With You," but it works surprisingly well as a party anthem. That same carefree spirit can be heard in the feminist track "Raining Men," which features Nicki Minaj — their first of two collabs, as they joined forces again for "Fly," the final single off the rapper's iconic Pink Friday album. 

A playful ode to sadomasochism and bondage, "S&M" contains some of Rihanna's most provocative lyrics: "Sticks and stones may break my bones/ But chains and whips excite me," she declares on the chorus. 

Banned in 11 countries upon its release, the accompanying video features Rihanna tied up in pink rope, dancing with a blowup doll, and donning a Playboy bunny-esque costume as damning newsreels about herself flash across the screen. But Rihanna's love of kink made her an even bigger star: "S&M" produced a remix with Britney Spears and earned Rihanna her 10th No. 1 single. With this feat, she became the youngest artist to attain the most chart-toppers in a five-year span.

On "Man Down," Rihanna's patois is in full effect as she takes listeners through a gripping tale about murdering her abuser. "What started out as a simple altercation/ Turned into a real sticky situation," she laments in the opening verse, amplified by siren noises in the background. There's something so satisfying about Rihanna's Bajan accent as she unfurls "Rum-pum-pum-pum" repeatedly over an intensifying reggae beat that would make Sister Nancy and Bob Marley proud.

Nominated for Album Of The Year at the 2021 GRAMMYs, Loud is Rihanna's second most commercially successful LP — and for good reason. It was especially refreshing to see Rihanna emerge from one of the darkest periods of her life as exuberant as ever.

An Unapologetic Queen

Sonically and thematically, Talk That Talk doesn't break new ground, but Rih's DGAF attitude is front and center with plenty of sexual innuendos: Songs like "S&M" and "Rude Boy" seem pretty tame next to "Cockiness (Love It)," which features longtime friend-turned-boyfriend A$AP Rocky on its remix. "Suck my cockiness/ Lick my persuasion/ Eat my poison/ And swallow your pride down, down," she commands in the tantalizing chorus.

At just over a minute long, "Birthday Cake" leaves nothing to the imagination ("It's not even my birthday, but he wanna lick the icing off"). Rihanna controversially released a full-length version in the form of a remix with Chris Brown.

On an album that mostly sees Rihanna singing about her sexual fantasies, "We All Want Love" pulls back the curtain as it reveals her desire for true love: "And some say love ain't worth the buck/ But I'll give my last dime/ To have what I've only been dreaming about." 

Her longing continues in "Where Have You Been," which flaunts Rihanna's versatility, flipping Geoff Mack's 1959 country song "I've Been Everywhere" into an infectious EDM banger. Lead single "We Found Love" is undeniably the biggest hit to stem from the Talk That Talk era, spending 10 consecutive weeks atop the Hot 100. 

Boosting Calvin Harris' career, "We Found Love" presents one juxtaposition after the other: dark yet gleaming, euphoric yet sobering, fraught yet hopeful. Rihanna relies on more than just evocative lyrics to tell her story; accompanying synthesizers and alarm bells help to paint a picture as well. Met with controversy, its intense visuals portraying a drug-fueled, toxic relationship — and featuringwhat many speculated was a Chris Brown look-alike — earned RiRi a GRAMMY for Best Long Form Music Video in 2013.

Seven years into an already extraordinary career, 2012's Unapologetic became Rihanna's first album to debut at No. 1 on the all-genre Billboard 200 chart. Its lead single "Diamonds" resonated in an equally major way, giving Rih her 12th No. 1 on the Hot 100.

Written by Sia, the power ballad kicked off another exciting era for the Barbadian singer, who unleashes an impassioned vocal performance. One of Rihanna's most precious offerings to date, "Diamonds" emerged as a self-love mantra due to its uplifting "Shine bright like a diamond" chant.

Vocally, Rihanna's strength lies in her ability to evoke raw emotion à la "Stay." Featuring Mikky Ekko, the stripped-down, slow-burning piano ballad narrowly missed the top spot on the Hot 100 but gave Rihanna her 24th top 10 hit, surpassing Whitney Houston's record of 23 in 2013.

Her swagger is boisterous in "Phresh Out the Runway," "Jump," and strip club anthem "Pour It Up," but "Nobody's Business" really drives home the album's theme of being unbothered. Her decision to join forces with Chris Brown yet again perplexed fans and critics alike, though the track itself is an irresistible production that features a genius interpolation of Michael Jackson's "The Way You Make Me Feel."

Further down the track list, "Love Without Tragedy / Mother Mary" is as autobiographical as it gets, and further taps into Rihanna's emotionally vulnerable side. "Mr. Jesus, I'd love to be a queen/ But I'm from the left side of an island/ Never thought this many people would even know my name," she pleads in the seven-minute two-parter.

Unapologetic spawned fewer hit singles compared to Rihanna's previous efforts. Its win for Best Urban Contemporary Album at the 2014 GRAMMYs, however, proved that Rihanna's reign wasn't letting up anytime soon.

While recording her then-forthcoming album, ANTI, Rihanna delivered what is arguably the single most unapologetic moment of her career: "Bitch Better Have My Money." The backstory is almost inconceivable given Rihanna's awe-inspiring billionaire status, but in 2009, Rihanna faced bankruptcy due to her accountants mishandling her funds — and thus "Bitch" was born six years later in 2015.

With lyrics like "Your wife in the backseat of my brand new foreign car" over a cryptic-sounding trap beat and an accompanying video depicting kidnapping and torturing her debtors, "Bitch" is not for the faint-hearted. The one-off single is so quintessentially Rihanna that it notably kicked off her Super Bowl halftime show.

An In-Demand Collaborator

While bestowing hit after hit on her own, Rihanna generously lent her distinct voice to some of her biggest peers. 2008 marks one of the earliest instances of her Midas touch: She flirts with funk in Maroon 5's underappreciated "If I Never See Your Face Again" before hopping on T.I.'s "Live Your Life," which shot straight to No. 1 on the Hot 100.

In 2009, Rihanna joined Jay-Z and Kanye West for the militant "Run This Town," sounding defiant as ever in the intro. She was called upon again for West's horn-laden "All of the Lights," flying solo on the hook followed by a star-studded choir that included Alicia Keys, John Legend, Fergie, and Elton John. Both larger-than-life productions won GRAMMYs for Best Rap/Sung Collaboration in 2010 and 2012, respectively.

In between joining forces with Hov and Ye, Rihanna assisted Eminem in "Love the Way You Lie," which struck a nerve with many for its gut-wrenching lyrics shedding a light on abusive relationships. (Rih recorded an equally moving sequel for her Loud album.) Three years later, the two confronted their inner demons in "The Monster," and their musical chemistry scored a GRAMMY in 2015 for Best Rap/Sung Collaboration.

Amid smash collabs, Rihanna and Coldplay's intricate "Princess of China" number gets lost in the shuffle, but it speaks to her charm as it's the band's first album (2011's Mylo Xyloto) to feature another artist. Another overlooked jam, her sultry "Can't Remember to Forget You" duet with Shakira sees both stars trade lines about struggling to let go of an undeserving lover.

On paper, a collaboration between Rihanna, Kanye West, and Sir Paul McCartney may seem strange, but the unlikely trio is further proof that opposites attract. Their "FourFiveSeconds" is a pop-folk hybrid with a universal message about carrying the weight of the world on your shoulders. It's yet another example of Rihanna's willingness to push past her comfort zone to create something unique.

A year later, Rihanna got listeners on their feet by way of the Taylor Swift-penned "This Is What You Came For" with Calvin Harris. Understated compared to the duo's previous megahits ("We Found Love" and "Where Have You Been"), Harris' signature DJing style and Rih's ethereal vocals are a perfect match.

In 2017, Rih, DJ Khaled and Bryson Tiller dropped the song of the summer with "Wild Thoughts," which heavily borrows from Carlos Santana's 1999 GRAMMY-winning "Maria Maria." It may be DJ Khaled's song, but RiRi owns it from the very moment she utters, "I don't know if you could take it/ Know you wanna see me nakey, nakey, naked." The bop reached No. 2 on the Hot 100.

She spits bars in Kendrick Lamar's "Loyalty" and "Lemon" with N.E.R.D., the latter of which comes close to rivaling your favorite rappers' verses: "You can catch me, Rih, in the new La Ferrar'/ And the truck behind me got arms/ Yeah, longer than LeBron/ Just waitin' for my thumb like The Fonz."

No matter what genre Rihanna touches or what artist she links up with, she brings her full self to each session whilst completely immersing herself into the music — taking on different personas to make the collab well worth it.

An Artist Fully Realized

With 13 No. 1s and twice as many top 10 hits under her belt, Rihanna set out to create timeless music instead of chasing a radio-friendly formula with her 2016 magnum opus, ANTI.

But that shift began with 2015's criminally underrated "American Oxygen." Her most political statement at the time, the goosebump-inducing lyrics detail Rihanna's journey as an immigrant, foreshadowing her then soon-to-be massive Fenty Beauty success. "We sweat for a nickel and a dime/ Turn it into an empire," she sings in the chorus.

Released four years after Unapologetic — her longest gap between albums at the time — ANTI illustrated Rihanna's greater desire for quality over quantity. "I needed the music to match my growth," she told Vogue in 2016 about the making of ANTI. "I didn't want to get caught up with anything the world liked, anything the radio liked, anything that I liked, that I've already heard. I just wanted it to be me."

The black-and-white, red paint-splattered album cover signals a rebirth, featuring a real-life image of Rihanna as a child. ANTI lives up to its name in its first 40 seconds, via opening track "Consideration." The minute she declares, "I got to do things my own way, darling," it's apparent that ANTI is not your average Rihanna album.

Lead single "Work" is the closest to pre-ANTI Rihanna on an album that defies expectations. But the dancehall masterpiece is one of a kind for Rih's refusal to water down the Jamaican patois (different from her native language of Bajan Creole) — proving that she is fully aware of her impact as one of the biggest Caribbean-born artists to make it in the U.S.

Many non-understanding listeners described it as "gibberish" at the time. Yet, the general public didn't seem to mind: About a month after its release, "Work" became Rihanna's 14th and longest-running chart-topper on the Hot 100. Weeks later, ANTI became her second LP to top the Billboard 200 chart. Subsequently, Rihanna held the No. 1 spots on the Billboard 200 and Hot 100 simultaneously, her second time achieving such an impressive feat.

Read More: How Rihanna's "Work" Reinvigorated Dancehall

ANTI is full of pleasant surprises that show off her artistry. Rihanna comes out of left field with the Prince-inspired "Kiss It Better," the album's second single, which sees the superstar falling back on addictive sex that "feels like crack" to justify a destructive relationship. "Same Ol' Mistakes" is a cover of psychedelic rock band Tame Impala's "New Person, Same Old Mistakes" — her first time remaking another artist's song for her own album since "You Don't Love Me (No, No, No)" on Music of the Sun. The Western-themed "Desperado" lends itself particularly well to covers by country artists, while the Dido-sampling "Never Ending" conveys the uncertainty she feels about entering a new relationship.

Elsewhere on ANTI, Rihanna drunk dials an ex ("Higher"), compares smoking weed to her lover ("James Joint"), and chastises a guy for getting emotionally attached after their fling ("Needed Me"). The latter song contains one of Rihanna's most empowering lyrics: "Didn't they tell you that I was a savage?/ F— ya white horse and ya carriage," she asserts in the pre-chorus.

Her voice sounds stronger than ever on "Love on the Brain," a doo-wop ballad resembling Etta James. But Rihanna makes it her own thanks to the bluntness of lines like "It beats me black and blue but it f— me so good."

The deep cuts on ANTI aren't merely fillers, and even rival some of the album's biggest hits. For instance, "Sex with Me" is featured on the deluxe edition as a bonus track, but managed to crack the Hot 100 at No. 83 and reach No. 8 on the R&B/Hip-Hop Airplay chart. Furthermore, the deluxe edition consists of 16 tracks, half of which topped the Dance Club Songs chart — smashing the record (previously held by Katy Perry's Teenage Dream) for the most No. 1s from a single album.

Accolades aside, ANTI is proof that magic happens when an artist of Rihanna's caliber follows their own instincts in pursuit of creating a body of work — one that can outlast them and continue to inspire generations to come.

Ever since ANTI, Rihanna's devoted fanbase has been begging for a new album, with Rih playfully trolling them with responses like "I lost it" and Instagram captions that read, "Me listening to R9 by myself and refusing to release it."

Her much-awaited return to music came at the tail end of 2022. The hitmaker twice contributed to the GRAMMY-nominated Black Panther: Wakanda Forever soundtrack: "Born Again" and "Lift Me Up," the latter of which helped Rihanna score her first Oscar and Golden Globe nominations in 2022 and 2023, respectively. With the glorious "Lift Me Up," she found herself in the top 10 for the first time since 2017's "Wild Thoughts."

While the world is still anticipating her ninth studio album, Rihanna — now a mom of two boys — continues to make her own rules and move at her own pace. But as she's proven time and time again, it's always worth the wait.

The Rihanna Essentials: 15 Singles To Celebrate The Singer's Endless Pop Reign

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Rihanna attends Marvel Studios' "Black Panther 2: Wakanda Forever" Premiere on October 26, 2022 in Hollywood, California.

Photo: Axelle/Bauer-Griffin / FilmMagic / Getty Images

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10 Love Songs That Have Nothing to Do With Love: From "Every Breath You Take" To "Baby It's Cold Outside"

Don't let the song titles fool you. From misogynist attitudes to tales of coercion and even a secret pregnancy, many popular love songs aren't about love at all.

GRAMMYs/Feb 14, 2024 - 03:46 pm

Many studies on love have proven that it seems to be a trait present throughout species. Although it's undeniable that the capacity for love is universal, evidence suggests love manifests differently across individuals. That is why, for many people, love is undefinable, with the word meaning something for one and something else for another. 

This point has never been proven more true than in love songs. Numerous musicians and bands have sung about love, but their definition or meaning of the word and yours might be wholly different. You would be surprised to learn how many love songs have absolutely nothing to do with emotional or physical love.

When you delve beneath the surface, "love" songs are sometimes twisted, uncomfortable, sadistic, and unsavory. So, let's look at 10 love songs with nothing to do with love and everything to do with what they shouldn’t. 

"Every Breath You Take" - the Police 

When the Police released "Every Breath You Take" in 1983, it immediately became a huge hit, reaching No.1 on U.S., UK, Canadian, Irish, and South African charts. On the surface, this song seems romantic, which is why it made its way into numerous movie scenes and weddings, but the lyrics are uncomfortable and prove the song is not actually about love. 

Frontman Sting sings, "I'll be watching you," and, "Oh, can't you see, you belong to me?" about the song's object of affection. Rather than lyrics about a lover, it's believed that the song is about a stalker. At the time Sting was suffering a mental breakdown, making the verses infinitely more evil.

In fact, Sting himself said: "I think it's a nasty little song, really rather evil. It's about jealousy and surveillance and ownership."

"Rollercoaster of Love" - Ohio Players 

On the surface, the lyrics "It's a rollercoaster ride/we're on top for the moment/ and then we'll take that dive" seem to describe a relationship's exhilarating ups and downs. However, there has been much debate over the years about the true meaning behind the Ohio Players' staple. 

The most popular theory is that the song is about life's ups and downs, not love, but we'll never know. According to late frontman Leroy Bronner who wrote the tune, "To this day, I don't know what I wrote." He continued, "The words didn't make sense to me. But it was a hit."

The song also has a much darker recording humor, which further alienates it from the genre of love songs. According to the rumor to which the band responded "No comment," the scream on the track was the sound of a woman being murdered in the recording studio. 

The woman's death is an urban legend, but the band decided to leave it in as a joke and as a way to create buzz for the song, with the actual scream belonging to keyboard player Billy Beck. 

"Can't Feel My Face" - the Weeknd  

The Weeknd is well known for penning lyrics that have multiple meanings, so it's not surprising that his hit track "Can't Feel My Face" isn't really about love. 

With the lyrics: "I can't feel my face when I'm with you/But I love it" and "And I know she'll be the death of me, at least we'll both be numb/And she'll always get the best of me; the worst is yet to come." It sounds like a dark love song about a man who is so in love that he loses all control, which is plausible, but it's more likely the song is about cocaine. 

According to Billboard, the song is about drug dependency, and the Weeknd is crooning about cocaine and likening it to a bad relationship. The Weeknd had hinted at the song being about drugs when he commented: "I just won a new award for a kids' show, Talking 'bout a face numbing off a bag of blow." Unfortunately, it's not very romantic. 

"Umbrella" - Rihanna

Most believe that one of Rihanna's most famous songs is about a woman comforting her partner and explaining that she will be there for him through the good and bad times. "Baby 'cause in the dark you can't see shiny cars/And that's when you need me there. With you, I'll always share," she sings.

However, a few people believe "Umbrella" is about the corruption of a person's soul – Rhianna's in this case. Some believe that the 2007 hit is about Rhianna welcoming the devil into her heart, body, and soul. While this is more of a conspiracy theory than anything else,  a pastor recently posted on TikTok that he came back from hell, and "Umbrella" was one of the songs being used to torture individuals. 

"All I Wanna Do is Make Love To You" -  Heart

If you listen carefully to the lyrics in "All I Wanna Do Is Make Love To You," it's clear that the 1990 song actually about deceit. 

Nancy and Ann Wilson are singing about being in love with another man who cannot provide her with children because he is impotent — so she finds a willing one-night stand. She sings, "I didn't ask him his name, this lonely boy in the rain." When morning comes, the protagonist says "All I left him was a note/ I told him I am the flower; you are the seed. We walked in the garden; we planted a tree."

After some time has passed, she's unnerved to come across his path, presumably pregnant: "You can imagine his surprise when he saw his own eyes/I said please, please understand/I'm in love with another man/And what he couldn't give me was the one little thing that you can."

"Bad Romance" - Lady Gaga

"Bad Romance" was developed as an experimental pop record featuring elements of German techno and house. With more than 184 million YouTube streams, the 2008 track quickly became one of Lady Gaga's best songs. 

On the surface, "Bad Romance" centers on the pull of a love that's bad for you: "I want your ugly, I want your disease/I want your everything as long as it's free/I want your love." However, it's not so straightforward. 

Gaga said she drew inspiration from the paranoia she experienced while on tour. She also stated the song is about her attraction to unhealthy romantic romances that are not always about love. 

"Young Girl" - Gary Puckett and the Union Gap

Not all love is appropriate, as the song "Young Girl" by Gary Puckett and the Union Gap proves. This 1968 single is wholly inappropriate and creepy (and illegal), but it still managed to become one of the band's best-known songs. In fact, despite the lyrics being more about unsavory infatuation than love, it still reached No. 2 on the Billboard Hot 100 (just behind "(Sittin' On) The Dock of the Bay"). 

Initially, this song doesn't appear inappropriate with lyrics  "Young girl, get out of my mind" possibly referencing the romance of a slight age gap. But the group doubles down: "My love for you is way out of line/ Better run, girl/You're much too young, girl."

If these words aren't enough to prove the song is about being infatuated with an underage girl, you might be convinced by lead singer Gary Puckett singing, "Beneath your perfume and make-up you're just a baby in disguise" and "Get out of here before I have the time to change my mind." 

"Under My Thumb" - by the Rolling Stones

The Rolling Stones have had their share of controversy over the years, and it's not hard to see why when you consider the meaning behind many of their big hits. "Under My Thumb" might have been marketed as a love song, but it's about a relationship rooted in hate and control. 

With lyrics such as "Under my thumb/It's a squirmin' dog who's just had her day/Under my thumb/

A girl who has just changed her ways," it's apparent that Mick Jagger is singing less about heartbreak and more about power. The misogyny is so clear in this song that it made it into the book Under My Thumb: Songs That Hate Women and the Women That Love Them.

"Baby It's Cold Outside" - Dean Martin 

One of the most popular holiday season love songs, "Baby, It's Cold Outside" was written by Frank Loessser and performed by Dean Martin and Ella Fitzgerald. It's difficult to say if these musicians knew the song's sinister and controversial underbelly. 

"Baby It's Cold Outside" is about a man who pressures a woman to stay at his home by any means necessary. The woman in the song tries to give reasons why she cannot stay with lyrics like "My mother will start to worry" and "My father will be pacing the floor." Yet, her concerns are shot down at every turn, with the man using the bad weather outside to keep her captive. Fortunately, the song has been remade with consensual lyrics, thanks to Kelly Clarkson and John Legend

"You're Gorgeous" - Babybird

This song may have a happy rhythm, but if you pay attention to the lyrics, there is much more to this song than meets the eye. Although the song appears to be about a man who would do anything for his lady love, it is about exploitation. 

This song — the British group's biggest hit, from 1996 — is about a sleazy photographer who takes advantage of a young and naive model and photographs her for men's magazines. The lyrics "You got me to hitch my knees up/And pulled my legs apart" details the true nature of this song.

"People should never be told how to interpret a song," Babybird told the blog Essentially Pop. "So, if they thought it was romantic, then fine." He continued, "Sadly, very few people got the true meaning, which is about male predatory behavior, but in popular music, most critics are a little blind to correct interpretation."

Lovesick Or Sick Of Love: Listen To GRAMMY.com’s Valentine’s Day Playlist Featuring Taylor Swift, Doja Cat, Playboi Carti, Olivia Rodrigo, FKA Twigs & More

A Timeline Of Drake's GRAMMY Moments, From His First Win To Performances & Beefs
Drake in 2011, 2009, 2019, 2010 and 2011

Photos: Kevin Mazur/Wire; Steve Granitz/WireImage; Jeff Kravitz/FilmMagic; Larry Busacca/Getty Images For The Recording Academy

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A Timeline Of Drake's GRAMMY Moments, From His First Win To Performances & Beefs

Drake's relationship with the GRAMMYs has been all over the map. The five-time GRAMMY winner's comments about the Awards have sparked debate, as has his relationship to submitting his work for consideration.

GRAMMYs/Jan 16, 2024 - 03:02 pm

When Drake attended his first GRAMMY Awards in 2010, he was 23 and hadn’t yet released a debut album. By the time he received his nominations for the 2024 GRAMMYs — Best Rap Album, Best Rap Performance and Best Melodic Rap Performance for his collaborations with 21 Savage —  he was Spotify’s most-streamed artist of all time, and the holder of more Billboard chart records than we can possibly list in this intro. 

In between, his relationship with the Academy’s yearly showcase has been all over the map. He’s lost (mostly), won (five times), and performed alongside some of pop culture’s biggest names. But more to the point, starting in 2017 his public comments about — and during — the GRAMMYs have sparked debate. He’s gone back and forth about submitting his music for consideration, and even went as far as to demand that nominations be retracted (more on that later).

Drake is nominated for Best Rap Album among other awards at the 2024 GRAMMYs. Here is a year-by-year account of the relationship between one of music’s biggest stars and Music’s Biggest Night. 

2010 — 52nd GRAMMY Awards

Nominations: Best Rap Song ("Best I Ever Had"), Best Rap Solo Performance ("Best I Ever Had")

Performances: "Drop the World"/"Forever" with Eminem, Lil Wayne, and Travis Barker

This was Drizzy’s first GRAMMYs, and he was still green enough that he got "reassurance" from Eminem in advance of their performance. 

"He was like, 'Man, anytime you need to look over at me, don't get nervous. Just look over at me, man, and I'll give it back to you. Everything will be all right. Don't be nervous.' For him to say that to me — I feel like that was an important moment," Drake told MTV News at the time.

His first two nominations, both for "Best I Ever Had," came before he had even put out his debut album. And as you can see in an interview at the event, the awards circuit was new enough that his mother’s reaction to finding out that Drake was nominated was to text him a bunch of swear words. 

"I think she was excited," the rapper joked to a CNN reporter.

2011 — 53rd GRAMMY Awards

Drake performs with Rihanna

Nominations: Best New Artist, Best Rap Album (Thank Me Later), Best Rap Solo Performance ("Over"), Best Rap Performance by a Duo or Group ("Fancy" with Swizz Beatz and T.I.)

Performances: "What’s My Name" (with Rihanna)

This is the year that seems to sting Drake the most. Best New Artist was a tough battle, with Drizzy, Justin Bieber, Mumford & Sons, and Florence + the Machine in the mix. All of them lost to Esperanza Spalding, in a major upset

Drake’s bitterness about the moment lingers to this day. On his most recent album For All the Dogs, he has a surprisingly angry lyric about it: "Four GRAMMYs to my name, a hundred nominations/ Esperanza Spalding was gettin' all the praises/ I'm tryna keep it humble, I'm tryna keep it gracious/ Who give a f— Michelle Obama put you on her playlist?/ Then we never hear from you again like you was taken."

2012 — 54th GRAMMY Awards

Nominations: Album Of The Year (Rihanna’s Loud, as featured artist), Best Rap Performance ("Moment 4 Life" with Nicki Minaj), Best Rap/Sung Collaboration ("I’m On One" with DJ Khaled, Rick Ross, and Lil Wayne; "What’s My Name" with Rihanna)

This was Drake’s first year as a presenter, so he appears to be moving up in the award show hierarchy. But that doesn’t help him with hardware — he still goes home empty-handed. 

This is also the time that he has multiple nominations in the same category (in this case, two in Best Rap/Sung Collaboration), which is also a trend that would repeat throughout the years. 

2013 — 55th GRAMMY Awards

Wins: Best Rap Album (Take Care)

Nominations: Best Rap Performance ("HYFR [Hell Ya F—king Right]" with Lil Wayne), Best Rap Song ("The Motto" with Lil Wayne)

He finally wins! Drake gets his first victory (for Best Rap Album). Also, he is the only Canadian to win that year (sorry, Loreena McKennitt!) However, the big moment wasn't telecast and Drizzy hadn’t yet arrived at the ceremony. In a charming interview from later in the night, Drake recalled jumping out of his car in the middle of traffic to celebrate. There’s also a video of him receiving his GRAMMY in the mail after the fact, which is notable for him immediately taking a celebratory drink from the trophy.

2014 — 56th GRAMMY Awards

Nominations: Album Of The Year (Kendrick Lamar’s good kid, m.A.A.d city, as featured artist), Best Rap Album (Nothing Was the Same), Best Rap Performance ("Started From the Bottom"), Best Rap Song ("Started From the Bottom"; "F—in’ Problems" with ASAP Rocky, 2 Chainz, and Kendrick Lamar)

Drake gets five nominations — and again two in one category — with no wins. It’s hard to pinpoint where the tide might have turned regarding the rapper’s feelings about the institution, but this ceremony may well have been it. 

2015 — 57th GRAMMY Awards

Nominations: Album Of The Year (Beyoncé's Beyoncé, as featured artist), Best Rap Performance ("0 to 100 / The Catch Up"), Best Rap Song ("0 to 100 / The Catch Up"), Best Rap/Sung Collaboration ("Tuesday" with ILoveMakonnen)

Once again Drake gets an Album Of The Year nomination…for someone else’s album. It’s now the third time this has happened, following Rihanna and Kendrick Lamar. Still, four nominations during a year with no new album is impressive, and shows just how much of a fixture The Boy has become in the pop firmament at this point. 

2016 — 58th GRAMMY Awards

Nominations: Best Rap Album (If You’re Reading This It’s Too Late), Best Rap/Sung Collaboration ("Only" with Nicki Minaj, Lil Wayne, and Chris Brown), Best Rap Performance ("Back to Back"; "Truffle Butter" with Nicki Minaj and Lil Wayne), Best Rap Song ("Energy")

From four nominations in 2015 to five this year, tying his personal best from 2014. They are all for rap-related awards, perhaps because Drake didn’t release a "proper" album that might have ended up in one of the big categories — If You’re Reading This It’s Too Late had a convoluted rollout. 

2017 — 59th GRAMMY Awards

Wins: Best Rap/Sung Performance ("Hotline Bling"), Best Rap Song ("Hotline Bling")

Nominations: Album Of The Year (Views), Best Rap Album (Views), Record Of The Year ("Work" with Rihanna), Best Pop Duo/Group Performance ("Work" with Rihanna), Best R&B Song ("Come and See Me" with PartyNextDoor), Best Rap Performance ("Pop Style" with The Throne)

The results of this year marked the beginning of Drake’s public issues with the GRAMMYs. Drake didn't attend the ceremony and, in an interview just after the ceremony, he pushed back against his own victory, upset that "Hotline Bling," a song with no rapping, won two rap awards.

"Last night at that awards show, I’m a Black artist," he said. "I’m apparently a rapper, even though ‘Hotline Bling’ is not a rap song. The only category that they can manage to fit me in is in a rap category, maybe because I’ve rapped in the past or because I’m Black." 

He was also upset that his hit "One Dance" wasn’t nominated in any general categories. 

"There’s pop obligations that [the Recording Academy] have," he said. "And I fluked out and got one of the biggest songs of the year, that is a pop song, and I’m proud of that. I love the rap world and I love the rap community, but I write pop songs for a reason. I want to be like Michael Jackson.

"I won two awards last night, but I don’t even want them for some reason," he continued. "It just feels weird. It feels like you’re purposely trying to alienate me or pacify me by handing me something, putting me in that [rap] category because it’s the only place you can figure out where to put me." 

Perhaps because of these issues — it was never confirmed — he never submitted his 2018 project More Life for GRAMMY consideration. Regardless, he ended up with no nominations the following year.

2019 — 61st GRAMMY Awards

Wins: Best Rap Song ("God’s Plan")

Nominations: Album Of The Year (Scorpion), Best Rap Performance ("Nice for What"; "Sicko Mode" with Travis Scott, Swae Lee, and Big Hawk), Best Rap Song ("Sicko Mode" with Travis Scott, Swae Lee, and Big Hawk), Record Of The Year ("God’s Plan"), Song Of The Year ("God’s Plan")

This was a year that heightened the Drake/Recording Academy tension even further. First, he turned down a chance to perform during the ceremony. And then, during his acceptance speech for Best Rap Song, Drizzy let awards shows have it. 

"We play in an opinion-based sport, not a factual-based sport," he began. "Look, the point is, you already won if you have people singing your songs word for word, if you’re a hero in your hometown. You’re already winning, you don’t need this right here."

The broadcast went to commercial while he was still talking, something that fans thought was an intentional slight. The Academy said otherwise.

"During Drake’s speech there was a natural pause during his speech and at that moment the producers did assume that he was done and then cut to commercial," the Academy said in an official statement. "However the producers did speak with Drake following his speech and did offer him to come back on stage to finish whatever his thoughts were, but Drake said he was happy with what he said and didn’t have anything to add to it."

2020 — 62nd GRAMMY Awards

Nominations: Best R&B Song ("No Guidance" with Chris Brown), Best Rap Song ("Gold Roses" with Rick Ross)

Drake didn’t publicly react to his two losses this year, but he did speak out on a friend’s behalf. The superstar was upset that The Weeknd didn’t receive any nominations, and said so in an Instagram story. He went far enough as to say that awards shows like the GRAMMYs "may no longer matter" to up-and-coming artists.

"I think we should stop allowing ourselves to be shocked every year by the disconnect between impactful music and these awards and just accept that what once was the highest form of recognition may no longer matter to the artists that exist now and the ones that come after," Drake wrote. "It’s like a relative you keep expecting to fix up but they just can’t change their ways.

"The other day I said @theweeknd was a lock for either album or song of the year along with countless other reasonable assumptions and it just never goes that way," he continued. "This is a great time for somebody to start something new that we can build up over time and pass on to the generations to come."

He went on to list artists he believed should be been nominated: Lil Baby, Pop Smoke, Party Next Door, Popcaan, and "too many missing names to even name." 

2021 — 63rd GRAMMY Awards

Nominations: Best Rap Song ("Laugh Now Cry Later" with Lil Durk), Best Melodic Rap Performance ("Laugh Now Cry Later" with Lil Durk), Best Music Video ("Life Is Good" with Future)

Drake again misses out on everything he’s nominated for, which might have something to do with what happened the following year.

2022 — 64th GRAMMY Awards  

Nominations: Best Rap Album (Certified Lover Boy), Best Rap Performance ("Way 2 Sexy" with Future and Young Thug) - Both withdrawn

Things came to a boiling point in 2022. Drake was nominated for two awards, but his management asked the Academy to remove the nominations, which they did. 

2023 — 65th GRAMMY Awards

Wins: Best Melodic Rap Performance ("Wait For U" with Future and Tems)

Nominations: Album Of The Year (Beyoncé’s Renaissance, as songwriter), Best Rap Song ("Wait For U" with Future and Tems, "Churchill Downs" with Jack Harlow)

Drake didn’t submit any material for GRAMMY consideration this time around, but it didn’t stop him from receiving four nominations, and winning once. 

There was one other unexpected Drake-related Grammy moment this year as well. Several days before the ceremony, he made a speech at the Black Music Collective’s Recording Academy Honors event praising one of the evening’s honorees, Lil Wayne. Even when paying tribute to his mentor, Drake seemed to be referencing his ongoing issues with the Academy. His knowing winks to the camera whenever he said the phrase “Black Music Collective” appeared to be a nod to his ongoing complaints that contemporary Black artists were being ignored by the Grammys.  

2024 — 66th GRAMMY Awards

Nominations: Best Rap Album (Her Loss with 21 Savage), Best Rap Song ("Rich Flex" with 21 Savage"), Best Rap Performance ("Rich Flex" with 21 Savage), Best Melodic Rap Performance ("Spin Bout U" with 21 Savage)

In a sign that a change might be underway in the often-stormy relationship between Drake and the GRAMMYs, the rapper actually submitted material for nomination for the 2024 GRAMMYs. His collaboration with 21 Savage, Her Loss, was put up for Album of the Year (which it didn’t get a nom for) and Best Rap Album (which it did). The songs "Rich Flex" and "Spin Bout U" were also offered up in multiple categories, and each ended up with nominations. 

A Timeline Of Beyoncé's GRAMMY Moments, From Her First Win With Destiny's Child to Making History With 'Renaissance'

20 Iconic Hip-Hop Style Moments: From Run-D.M.C. To Runways
LL Cool J

Credit: Paul Natkin/Getty Images

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20 Iconic Hip-Hop Style Moments: From Run-D.M.C. To Runways

From Dapper Dan's iconic '80s creations to Kendrick Lamar's 2023 runway performance, hip-hop's influence and impact on style and fashion is undeniable. In honor of hip-hop's 50th anniversary, look back at the culture's enduring effect on fashion.

GRAMMYs/Nov 29, 2023 - 03:01 pm

In the world of hip-hop, fashion is more than just clothing. It's a powerful means of self-expression, a cultural statement, and a reflection of the ever-evolving nature of the culture.

Since its origin in 1973, hip-hop has been synonymous with style —  but the epochal music category known for breakbeats and lyrical flex also elevated, impacted, and revolutionized global fashion in a way no other genre ever has.   

Real hip-hop heads know this. Before Cardi B was gracing the Met Gala in Mugler and award show red carpets in custom Schiaparelli, Dapper Dan was disassembling garment bags in his Harlem studio in the 1980s, tailoring legendary looks for rappers that would appear on famous album cover art. Crescendo moments like Kendrick Lamar’s performance at the Louis Vuitton Men’s Spring-Summer 2023 runway show in Paris in June 2022 didn’t happen without a storied trajectory toward the runway.

Big fashion moments in hip-hop have always captured the camera flash, but finding space to tell the bigger story of hip-hop’s connection and influence on fashion has not been without struggle. Journalist and author Sowmya Krishnamurphy said plenty of publishers passed on her anthology on the subject, Fashion Killa: How Hip-Hop Revolutionized High Fashion, and "the idea of hip hop fashion warranting 80,000 words." 

"They didn't think it was big enough or culturally important," Krishnamurphy tells GRAMMY.com, "and of course, when I tell people that usually, the reaction is they're shocked."

Yet, at the 50 year anniversary, sands continue to shift swiftly. Last year exhibitions like the Fashion Institute of Technology’s Fresh, Fly, and Fabulous: Fifty Years of Hip-Hop Style popped up alongside notable publishing releases including journalist Vikki Tobak’s, Ice Cold. A Hip-Hop Jewelry Story. Tabak’s second published release covering hip-hop’s influence on style, following her 2018 title, Contact High: A Visual History of Hip-Hop.

"I wanted to go deeper into the history," Krishnamurphy continues. "The psychology, the sociology, all of these important factors that played a role in the rise of hip-hop and the rise of hip-hop fashion"

What do the next 50 years look like? "I would love to see a hip-hop brand, whether it be from an artist, a designer, creative director, somebody from the hip-hop space, become that next great American heritage brand," said Krishnamurphy.

In order to look forward we have to look back. In celebration of hip-hop’s 50 year legacy, GRAMMY.com examines iconic moments that have defined and inspired generations. From Tupac walking the runways at Versace to Gucci's inception-esque knockoff of Dapper Dan, these moments in hip-hop fashion showcase how artists have used clothing, jewelry, accessories, and personal style to shape the culture and leave an indelible mark on the world.

*The cover art to Eric B and Rakim’s* Paid in Full

Dapper Dan And Logomania: Luxury + High Fashion Streetwear

Dapper Dan, the legendary designer known as "the king of knock-offs," played a pivotal role in transforming luxury fashion into a symbol of empowerment and resistance for hip-hop stars, hustlers, and athletes starting in the 1980s. His Harlem boutique, famously open 24 hours a day, became a hub where high fashion collided with the grit of the streets.

Dapper Dan's customized, tailored outfits, crafted from deconstructed and transformed luxury items, often came with significantly higher price tags compared to ready-to-wear luxury fashion. A friend and favorite of artists like LL Cool J and Notorious B.I.G., Dapper Dan created iconic one-of-a-kind looks seen on artists like Eric B and Rakim’s on the cover of their Paid in Full album.

This fusion, marked by custom pieces emblazoned with designer logos, continues to influence hip-hop high fashion streetwear. His story — which began with endless raids by luxury houses like Fendi, who claimed copyright infringement — would come full circle with brands like Gucci later paying homage to his legacy.

Athleisure Takes Over

Hip-hop's intersection with sportswear gave rise to the "athleisure" trend in the 1980s and '90s, making tracksuits, sweatshirts, and sneakers everyday attire. This transformation was propelled by iconic figures such as Run-D.M.C. and their association with Adidas, as seen in photoshoots and music videos for tracks like "My Adidas."

*LL Cool J. Photo: Paul Natkin/Getty Images*

LL Cool J’s Kangol Hat

The Kangol hat holds a prominent place in hip-hop fashion, often associated with the genre's early days in the '80s and '90s. This popular headwear became a symbol of casual coolness, popularized by hip-hop pioneers like LL Cool J and Run-D.M.C. The simple, round shape and the Kangaroo logo on the front became instantly recognizable, making the Kangol an essential accessory that was synonymous with a laid-back, streetwise style.

*Dr. Dre, comedian T.K. Kirkland, Eazy-E, and Too Short in 1989. Photo: Raymond Boyd/Getty Images*

N.W.A & Sports Team Representation

Hip-hop, and notably N.W.A., played a significant role in popularizing sports team representation in fashion. The Los Angeles Raiders' gear became synonymous with West Coast hip-hop thanks to its association with the group's members Dr. Dre, Eazy-E, and Ice Cube, as well as MC Ren.

 *Slick Rick in 1991. Photo: Al Pereira/Getty Images/Michael Ochs Archives*

Slick Rick’s Rings & Gold Chains

Slick Rick "The Ruler" has made a lasting impact on hip-hop jewelry and fashion with his kingly display of jewelry and wealth. His trendsetting signature look — a fistful of gold rings and a neck heavily layered with an array of opulent chains — exuded a sense of grandeur and self-confidence. Slick Rick's bold and flamboyant approach to jewelry and fashion remains a defining element of hip-hop's sartorial history, well documented in Tobak's Ice Cold.

Tupac Walks The Versace Runway Show

Tupac Shakur's runway appearance at the 1996 Versace runway show was a remarkable and unexpected moment in fashion history. The show was part of Milan Fashion Week, and Versace was known for pushing boundaries and embracing popular culture in their designs. In Fashion Killa, Krishnamurpy documents Shakur's introduction to Gianni Versace and his participation in the 1996 Milan runway show, where he walked arm-in-arm with Kadida Jones.

*TLC. Photo: Tim Roney/Getty Images*

Women Embrace Oversized Styles

Oversized styles during the 1990s were not limited to menswear; many women in hip-hop during this time adopted a "tomboy" aesthetic. This trend was exemplified by artists like Aaliyah’s predilection for crop tops paired with oversized pants and outerwear (and iconic outfits like her well-remembered Tommy Hilfiger look.)

Many other female artists donned oversized, menswear-inspired looks, including TLC and their known love for matching outfits featuring baggy overalls, denim, and peeking boxer shorts and Missy Elliott's famous "trash bag" suit worn in her 1997 music video for "The Rain." Speaking to Elle Magazine two decades after the original video release Elliot told the magazine that it was a powerful symbol that helped mask her shyness, "I loved the idea of feeling like a hip hop Michelin woman."

Diddy Launches Sean John

Sean "Diddy" Combs’ launch of Sean John in 1998 was about more than just clothing. Following the success of other successful sportswear brands by music industry legends like Russell Simmons’ Phat Farm, Sean John further represented a lifestyle and a cultural movement. Inspired by his own fashion sensibilities, Diddy wanted to create elevated clothing that reflected the style and swagger of hip-hop. From tailored suits to sportswear, the brand was known for its bold designs and signature logo, and shared space with other successful brands like Jay-Z’s Rocawear and model Kimora Lee Simmons' brand Baby Phat.

 *Lil' Kim. Photo: Ron Galella/Ron Galella Collection via Getty Images*

Lil’ Kim Steals The Show

Lil' Kim’s daring and iconic styles found a kindred home at Versace with

In 1999, Lil' Kim made waves at the MTV Video Music Awards with her unforgettable appearance in a lavender jumpsuit designed by Donatella Versace. This iconic moment solidified her close relationship with the fashion designer, and their collaboration played a pivotal role in reshaping the landscape of hip-hop fashion, pushing boundaries and embracing bold, daring styles predating other newsworthy moments like J.Lo’s 2000 appearance in "The Dress" at the GRAMMY Awards.

Lil Wayne Popularizes "Bling Bling"

Juvenile & Lil Wayne's "Bling Bling" marked a culturally significant moment. Coined in the late 1990s by Cash Money Records, the term "bling bling" became synonymous with the excessive and flashy display of luxury jewelry. Lil Wayne and the wider Cash Money roster celebrated this opulent aesthetic, solidifying the link between hip-hop music and lavish jewelry. As a result, "bling" became a cornerstone of hip-hop's visual identity.

Jay-Z x Nike Air Force 1

In 2004, Jay-Z's partnership with Nike produced the iconic "Roc-A-Fella" Air Force 1 sneakers, a significant collaboration that helped bridge the worlds of hip-hop and sneaker culture. These limited-edition kicks in white and blue colorways featured the Roc-A-Fella Records logo on the heel and were highly coveted by fans. The collaboration exemplified how hip-hop artists could have a profound impact on sneaker culture and streetwear by putting a unique spin on classic designs. Hova's design lives on in limitless references to fresh white Nike kicks.

Daft Punk and Pharrell Williams. Photo: Mark Davis/WireImage

Pharrell Williams' Hat At The 2014 GRAMMYs

Pharrell Williams made a memorable red carpet appearance at the 2014 GRAMMY Awards in a distinctive and oversized brown hat. Designed by Vivienne Westwood, the hat quickly became the talk of the event and social media. A perfect blend of sartorial daring, Pharrell's hat complemented his red Adidas track jacket while accentuating his unique sense of style. An instant fashion moment, the look sparked innumerable memes and, likely, a renewed interest in headwear.

Kanye’s Rise & Fall At Adidas (2013-2022)

Much more than a "moment," the rise and eventual fall of Kanye’s relationship with Adidas, was as documented in a recent investigation by the New York Times. The story begins in 2013 when West and the German sportswear brand agreed to enter a partnership. The collaboration would sell billions of dollars worth of shoes, known as "Yeezys," until West’s anti-semitic, misogynistic, fat-phobic, and other problematic public comments forced the Adidas brand to break from the partnership amid public outrage.

Supreme Drops x Hip-Hop Greats

Supreme, with its limited drops, bold designs, and collaborations with artists like Nas and Wu-Tang Clan, stands as a modern embodiment of hip-hop's influence on streetwear. The brand's ability to create hype, long lines outside its stores, and exclusive artist partnerships underscores the enduring synergy between hip-hop and street fashion.

*A model walks the runway at the Gucci Cruise 2018 show. Photo: Pietro D'Aprano/Getty Images*

Gucci Pays "homage" to Dapper Dan

When Gucci released a collection in 2017 that seemingly copied Dapper Dan's distinctive style, (particularly one look that seemed to be a direct re-make of a jacket he had created for Olympian Dionne Dixon in the '80s), it triggered outrage and accusations of cultural theft. This incident sparked a conversation about the fashion industry's tendency to co-opt urban and streetwear styles without proper recognition, while also displaying flagrant symbols of racism through designs.

Eventually, spurred by public outrage, the controversy led to a collaboration between Gucci and Dapper Dan, a significant moment in luxury fashion's acknowledgement and celebration of the contributions of Black culture, including streetwear and hip-hop to high fashion. "Had Twitter not spotted the, "Diane Dixon" [jacket] walking down the Gucci runway and then amplified that conversation on social media... I don't think we would have had this incredible comeback," Sowmya Krishnamurphy says.

A$AP Rocky x DIOR

Self-proclaimed "Fashion Killa" A$AP Rocky is a true fashion aficionado. In 2016, the sartorially obsessed musician and rapper became one of the faces of Dior Homme’s fall/winter campaign shot by photographer Willy Vanderperre — an early example of Rocky's many high fashion collaborations with the luxury European brand.

A$AP Rocky's tailored style and impeccable taste for high fashion labels was eloquently enumerated in the track "Fashion Killa" from his 2013 debut album Long. Live. ASAP, which namedrops some 36 luxury fashion brands. The music video for "Fashion Killa" was co-directed by Virgil Abloh featuring a Supreme jersey-clad Fenty founder, Rihanna long before the two became one of music’s most powerful couples. The track became an anthem for hip-hop’s appreciation for high fashion (and serves as the title for Krishnamurphy’s recently published anthology). 

*Cardi B. Photo: Steve Granitz/WireImage*

Cardi B Wears Vintage Mugler At The 2019 GRAMMYs

Cardi B has solidified her "it girl" fashion status in 2018 and 2019 with bold and captivating style choices and designer collaborations that consistently turn heads. Her 2019 GRAMMYs red carpet appearance in exaggerated vintage Mugler gown, and many custom couture Met Gala looks by designers including Jeremy Scott and Thom Browne that showcased her penchant for drama and extravagance.

But Cardi B's fashion influence extends beyond her penchant for custom high-end designer pieces (like her 2021 gold-masked Schiaparelli look, one of nine looks in an evening.) Her unique ability to blend couture glamour with urban chic (she's known for championing emerging designers and streetwear brands) fosters a sense of inclusivity and diversity, and makes her a true trendsetter.

Beyoncé & Jay-Z in Tiffany & Co.’s "About Love" campaign

The power duo graced Tiffany & Co.'s "About Love'' campaign in 2021, showcasing the iconic "Tiffany Yellow Diamond," a 128.54-carat yellow worn by Beyoncé alongside a tuxedo-clad Jay-Z. The campaign sparked controversy in several ways, with some viewers unable to reconcile the use of such a prominent and historically significant diamond, sourced at the hands of slavery, in a campaign that could be seen as commercializing and diluting the diamond's cultural and historical importance. Despite mixed reaction to the campaign, their stunning appearance celebrated love, adorned with Tiffany jewels and reinforced their status as a power couple in both music and fashion.

Kendrick Lamar Performs At Louis Vuitton

When Kendrick Lamar performed live at the Louis Vuitton Men’s spring-summer 2023 runway show in Paris in June 2022 following the passing of Louis Vuitton’s beloved creative director Virgil Abloh, he underscored the inextricable connection between music, fashion and Black American culture.


Lamar sat front row next to Naomi Campbell, adorned with a jeweled crown of thorns made from diamonds and white gold worth over $2 million, while he performed tracks including "Savior," "N95," and "Rich Spirit'' from his last album, Mr. Morale and the Big Steppers before ending with a repeated mantra, "Long live Virgil." A giant children’s toy racetrack erected in the Cour Carrée of the Louvre became a yellow brick road where models marched, clad in designer looks with bold, streetwear-inspired design details, some strapped with oversized wearable stereo systems.

Pharrell Succeeds Virgil Abloh At Louis Vuitton

Pharrell Williams' appointment as the creative director at Louis Vuitton for their men's wear division in 2023 emphasized hip-hop's enduring influence on global fashion. Pharrell succeeded Virgil Abloh, who was the first Black American to hold the position.

Pharrell's path to this prestigious role, marked by his 2004 and 2008 collaborations with Louis Vuitton, as well as the founding of his streetwear label Billionaire Boy’s Club in 2006 alongside Nigo, the founder of BAPE and Kenzo's current artistic director, highlights the growing diversity and acknowledgment of Black talent within high fashion.

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