By 2002, it was pretty clear that Justin Timberlake was an icon in the making. He was positioned as the unofficial frontman of *NSYNC, who were still riding high as one of the biggest boy bands of all time. But Timberlake was eager to ditch the ramen-noodle hair and family-friendly persona for a project that better reflected his artistry — little did he know, it'd solidify him as a superstar.

Justified, Timberlake's debut solo album, arrived on Nov. 5. The 13-track LP delved into the singer's R&B and old-school influences, artistically re-introducing himself while laying the groundwork for the global solo stardom to come.

The album came just six months after <em>NSYNC wrapped what would become their final tour and began an indefinite hiatus. At the time, he insisted the band was "in no danger" amid his solo venture. "There's no reason my solo career and </em>NSYNC can't coexist in the same universe," he told the New York Post.

That quickly proved difficult — Justified was a commercial success, debuting at No. 2 on the Billboard 200 and spawning two top-five singles. Within the next year, the album sold 3 million copies. Timberlake headlined arenas around the world, became the face of a McDonald's campaign, and landed his first double-duty hosting and performing gig on Saturday Night Live. A 2003 Rolling Stone cover story may have epitomized that one reason he could no longer coexist with his *NSYNC bandmates: "Justin Timberlake: The New King of Pop."

The Michael Jackson homage was fitting, as half of Justified was intended for the late icon. As Pharrell Williams confirmed in 2020, he and Chad Hugo (together, known as the Neptunes, who co-wrote and co-produced Justified) initially pitched their album contributions to Jackson. After Jackson declined, the Neptunes brought them to Timberlake, and the R&B-leaning sounds were exactly what he was looking for.

"I was trying to make a multi-dimensional record; a record that captured the vibe of my favorite time in music, the '60s," Timberlake told Billboard in 2002. "For the six weeks that we worked on these songs, I got to live in my own musical dream world and play a little hip-hop, a little old-school R&B, a little classic rock. It was so much fun — and I learned a lot about making music in a totally different way than I was used to."

Those old-school influences come through on cuts like "Let's Take a Ride" and "Last Night," but the prominent takeaway from Justified is that Timberlake was no longer a fresh-faced pop heartthrob. Racier lyrics ("I could think of a couple positions for you" in "Right For Me") and elevated, hip-hop-leaning production (helmed by The Neptunes, Timbaland and Scott Storch) presented a more mature sound that helped him graduate from teen stardom to full-fledged artistry.

Justified also set a new standard for solo stars emerging from a pop group, as his peers who tried before him couldn't quite make the same impact. The Backstreet Boys' Nick Carter released his first solo effort, Now or Never — coincidentally, just one week prior to Justified's arrival — to rather disappointing results, and each of the five Spice Girls' solo albums failed to make major waves. And really, until Harry Styles, no other former boy bander has managed to achieve such success since.

Between its commercial performance and sophisticated sound, Justified was arguably the first time an artist from a contemporary pop group was taken seriously as a solo act. Lead single "Like I Love You" helped set the tone ahead of the album's release, its fiery guitar and drum lines ushering in the more mature sound. The track also scored Timberlake his first solo GRAMMY nomination in 2003.

His subsequent singles — the searing "Cry Me a River" and the dance floor-ready "Rock Your Body" — were what sealed his fate as a solo star, both landing in the top five of the Billboard Hot 100. "Cry Me A River" is still one of Timberlake's biggest songs to date, and earned him a GRAMMY for Best Male Pop Vocal Performance in 2004.

The 2004 GRAMMYs marked another pivotal moment for Timberlake. Just one week after being part of the infamous Super Bowl wardrobe malfunction with Janet Jackson, the singer took to the GRAMMY stage to perform another Justified single, "Señorita," as well as his GRAMMY-nominated collaboration with the Black Eyed Peas, "Where Is The Love." Timberlake was nominated for a total of five awards that night — among them, the coveted Album Of The Year for Justified — and took home two golden gramophones, including the GRAMMY for Best Pop Vocal Album.

Twenty years later, Timberlake now has 10 GRAMMYs and 39 nominations, five No. 1 hits, four No. 1 albums, a Super Bowl halftime headlining gig, and even an acclaimed acting career. When it comes to his evolution from boy-bander to solo superstar, Timberlake may have put it best himself in the 2002 Billboard interview: "There's a lot more to me than people have previously believed." 

Timberlake certainly proved that — and justified his place as the new king of pop. 

'Spiceworld' At 25: How The Spice Girls' Feminine Enthusiasm & Camp Became A Beacon For Queer Youth

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.

Listen To GRAMMY.com's 50th Anniversary Of Hip-Hop Playlist: 50 Songs That Show The Genre's Evolution

Thirty years ago, a rap music legend began his journey to immortality — and to Martha Stewart.

Most in-the-know music fans were aware of Snoop Doggy Dogg (as he was then known) because of his collaborations with Dr. Dre. First there was "Deep Cover" from the soundtrack of the film of the same name. Then there were his memorable contributions to Dre's The Chronic, which came out in late 1992. 

So the world was primed for Snoop's solo debut Doggystyle when it was released into the world on November 23, 1993. The album sold around 800,000 copies in its first week, and set the stage for Snoop to become a superstar, one who would eventually reach a stage of pop-culture ubiquity that mid-90s rap fans — and those people who saw his scowl on the cover of Newsweek as the literal face of the question of whether rap was too violent — could have never imagined.

To celebrate the anniversary of Doggystyle's release, GRAMMY.com is revisiting the D-O-double-G's biggest and best musical moments. A quick note: this list does not include songs that appear on another artist's album (hey, we had to draw the line somewhere!), so there's no "Nuthin' But A 'G' Thang" or "2 of Amerikaz Most Wanted." And we tried to pull from all eras of his career, so it's not all Doggystyle (though you should, of course, listen to that classic in its entirety). 

So with all that said, here we are: 15 of Snoop Dogg's most popular and most dynamic songs. 

"Deep Cover" with Dr. Dre, Deep Cover soundtrack (1992)

Snoop's very first recorded song — his introduction to the world at large — occurred over a Dre beat so powerful, with a bassline so iconic, that it became the foil for not one, not two, but three classic songs (plus a nasty Biggie freestyle). The duo's lyrical chemistry was undeniable as they traded verses throughout. And, of course, there's the song's chorus, in which Snoop introduced California penal code 187 into the national lexicon.

The track and its video loosely parallel the plot of the movie on whose soundtrack it appears, the absolutely nuts (and surprisingly entertaining) Deep Cover, directed by Bill Duke and starring Laurence Fishburne. 

"Who Am I (What's My Name)?" Doggystyle (1993)

This track wasn't just the world's introduction to Doggystyle — it lets fans know that the Dre-and-Snoop chemistry they'd heard on The Chronic was not a fluke. The track's George Clinton and P-Funk interpolations also showed that Dre was still in his bag, and Snoop's vocal performance was one for the ages. Still in his very early 20s, the rapper was adept at mythmaking, showing the audience how he would "step through the fog" and "creep through the smog" to deliver his charismatic raps.

As if that wasn't enough, the song's Fab 5 Freddy-directed video showed Snoop's sense of humor, as it featured the rapper and his compatriots morphing into literal dogs. 

"Gin and Juice," Doggystyle (1993)

Any rap fan of a certain age can not only spit this song word for word, but also quote pretty much every line in the video ("Snoop Doggy Dogg! You need to get a jobby-job"). Just say the words "Laid back…" to pretty much anyone who is at the age where they can say complete sentences, and you'll get "With my mind on my money and my money on my mind" in response.

The song and video created an image for Snoop that was fun-loving and comic — one that he rode (sometimes in a Chrysler) all the way to a decades-long career as a pitchman, TV host and overall personality that would at first glance seem incongruous for an avowed Crip from Long Beach. Beyond all the myth-making, though, it's just a fantastic song, one that Rolling Stone included in its 100 best rap songs of all time list.

"Gz and Hustlas," Doggystyle (1993)

This Doggystyle highlight begins with a hilarious skit that ends with a funny and profane punchline from a very young Bow Wow. It just gets better from there.

Snoop has said that this is one of his two personal favorites from his debut album. Not unrelatedly, he's also admitted that the whole thing was improvised while he was just checking a mic. And as we'll see on the "Afro Puffs" remix, freestyling Snoop is the best Snoop. That's certainly the case here. The sample of Bernard Wright's "Haboglabotribin" provides the perfect soundtrack for the ride. 

"Murder Was the Case," Doggystyle (1993)

This song is the Faustian tale of a young man who survives a shooting by selling his soul to the devil in exchange for eternal life and a life of riches and success. But, as always with these stories, the protagonist's greed gets the better of him, and the devil gets his due. The narrator ends the story locked up, with only a prison riot to look forward to.

It's a gripping tale that would have eerie real-life resonance when Snoop was actually charged with murder, a charge on which he was famously acquitted. He wrote the song before the incident, a coincidence that affected him so deeply that he decided that "maybe I shouldn't be writing about devilish s— like this."

"Afro Puffs (Extended Remix)" with The Lady of Rage, Above the Rim soundtrack (1994)

Snoop is at his best when he's in the moment — when he's relaxed, freestyling and rapping in his inimitable style about whatever is on his mind. His opening verse on this song is perhaps the quintessential example of that.

He sounds completely at ease, swinging, developing ideas in an unforced way. It's like you're in the studio with Snoop for two solid minutes, watching him warm up and get comfortable. It's a performance style he wouldn't duplicate on any other studio track, even the ones he would also make up on the spot. 

"Woof! (feat. Fiend and Mystikal)," Da Game Is To Be Sold, Not To Be Told (1998)

One of Snoop's first major business and stylistic switches happened in March 1998, when he signed to No Limit Records. What was a Long Beach gangsta rapper doing on a New Orleans label? Well, it turned out to be a pretty great fit, at least on "Woof!"

The track was the second single on Snoop's No Limit debut, and it featured two of the label's stars, Fiend and Mystikal. The Dogg fits perfectly on a track in the label's aggressive, chant-based Southern style (even the track's percussive dog barks manage to add intensity). Snoop adopts a more free rhythmic approach here, perhaps influenced by his all-over-the-beat labelmates. It's fascinating to hear, and it works amazingly well.

"B— Please (feat. Xzibit)," No Limit Top Dogg (1999)

One of the things Snoop is greatest at is, to put it in crass, unavoidable terms, pimp talk. "B— Please" might be his ultimate entry into the genre. This song features a memorable performance by Xzibit and some classic singing from Nate Dogg. And the Dr. Dre beat is instantly memorable. But what really puts the song over the top is the confidence and style with which Snoop orders an unnamed lady to "hem my coat and roll me some dope."

Bonus points go to this track for its sequel, which appeared on Eminem's The Marshall Mathers LP, and which features Em doing a hilarious Snoop impression.

"Lay Low (feat. Master P, Nate Dogg, Butch Cassidy, and Tha Eastsidaz)," The Last Meal (2000)

Yes, Xzibit wrote Snoop's verse on this classic posse cut featuring rapping contributions from the Eastsidaz and Snoop's then-label boss Master P. But that doesn't make the Doggfather's contribution any less smooth. It doesn't prevent Nate Dogg's hook from being an unstoppable ear worm. It doesn't make Dr. Dre's beat any less of a minimalist masterpiece. It doesn't make the Eastsidaz's appearances less effective. And it certainly doesn't diminish in any way the single best part of the song: Master P rapping, "They call me Jed Clampett for all the bread I got/ But they call me Bill Clinton for all the head I got."

"Beautiful (feat. Pharrell Williams and Charlie Wilson)," Paid Tha Cost To Be Da Bo$$ (2002)

Snoop teaming up with Pharrell gave the Dogg a much-needed early aughts career boost. It turned out that Snoop and P made an unbeatable combination, and one that we will see again later in this very list.

"Beautiful" features an instantly memorable beat whose repetitive syncopated rhythms immediately drive into the listener's skull and don't let up until the song is over. Add in Pharrell's so-off-key-they're-somehow-on vocals, and you have a track that stands out even in the era of Neptunes ubiquity. Snoop adds his own style and grace, and, somehow, a (presumably intentionally) charmingly awkward reference to Clueless.

"Drop It Like It's Hot (feat. Pharrell Williams)," R&G (Rhythm & Gangsta): The Masterpiece (2004)

Snoop and Pharrell made a number of great songs, but this is arguably their masterpiece. This No. 1 hit was so popular that even its ringtone version went double platinum. It was also nominated for a GRAMMY. But accolades and numbers are secondary.

What makes this track is the perfect melding of one the Neptunes' greatest non-Clipse minimalist beats with Snoop's laid-back rapping (and a verse from Pharrell in which he bends his approach towards Snoop's to superb effect). Snoop sounds so relaxed that you might miss all the tough talk, which is delivered in his patented stylish way ("Pistol-whip you, dip you, then flip you/ Then dance to this mothaf—in' music we Crip to"). 

"Think About It," Tha Blue Carpet Treatment (2006)

This is the song Snoop chose to demonstrate to his own son that after nearly 15 years in the rap world, he could still hold his own. He couldn't have made a better choice.

"Think About It" is dense, wordy, even "intellectual" — a word Snoop comes back to a few times in the track. It's also a seemingly incongruous mixture of aggressive rapping, where Snoop sounds like he's really pushing himself; with laid-back music reminiscent of 1970s soul. And yet that combination, which could be off-putting, somehow works to the advantage of both elements of the song, supplying the rapping with needed comfort and style; and the music with energy and drive.

"Sensual Seduction," Ego Trippin' (2007)

Sometimes known by its uncensored title "Sexual Eruption," this Shawty Redd-produced track was one of Snoop's biggest chart hits, making it all the way to No. 7 on the Billboard Hot 100. It's also a big left turn for him, featuring Auto-Tuned singing throughout, minus a rap verse in the middle.

The incredibly catchy number started its life as a Shawty Redd solo song called "Drifter," which got leaked and hit the radio. "Snoop wanted to buy that song," Shawty told me a few years back. "At the time, Sylvia Rhone was signing me to Universal/Motown as an artist, and I couldn't sell Snoop that song. So I ended up making ['Sensual Seduction']."

"Young, Wild & Free" (Snoop Dogg & Wiz Khalifa feat. Bruno Mars) Mac & Devin Go To High School (2011)

This track brings together Snoop and a younger weed-obsessed rapper, Wiz Khalifa. But what really makes it a winner is the addition of Bruno Mars, who at that time was in the middle of an absolutely unstoppable run with his crew the Smeezingtons as a hitmaker for both himself and others. This was "F— You"/ "Billionaire"/ "Nothin' on You"-era Bruno, and his composition and hook here is right up there with those pop masterpieces. Snoop and Wiz trade rhymes back and forth with a chemistry that, while perhaps plant-induced, can't be faked.

"I'm From 21st Street (feat. DJ Drama and Stressmatic)," Gangsta Grillz: I Still Got It (2022)

Snoop spent much of the past decade doing unusual one-offs (see 2013's reggae album Reincarnated and 7 Days of Funk, a funk project with DāM-FunK, or 2018's gospel compilation Snoop Dogg Presents Bible of Love, among others). So when he wanted to get back to his rap roots in 2022, he teamed with Gangsta Grillz mastermind DJ Drama to release a mixtape called I Still Got It. The project, and especially this song, more than proves the title correct.

Snoop tears up the Rick Rock-produced beat, sounding more energized and hungry than he has in a while. The subject matter may be somewhat well-trod ground (it's not far removed from his 1994 track "21 Jumpstreet," which could easily have made this list as well), but how he talks about his past, and the intensity he brings to it, shows that Snoop can still produce great music 30 years into his career. 

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"From bricks to Billboards, from grams to Grammys," Jay-Z rhymes on "Dirt Off Your Shoulder," a prime example of how his eighth LP, The Black Album, is dominated by his rags-to-riches story. Released Nov. 14, 2003, The Black Album was, ironically, intended to be the rapper's final chapter. But the album's remarkable commercial and critical success — it sold 3.5 million copies in the States to become his sixth consecutive number one on the Billboard 200 — instead furthered his magnitude and influence, only continuing his legacy of one of rap's greats.

Boasting no fewer than 12 of the era's hottest producers (The Neptunes, Just Blaze, Timbaland, to name a few), The Black Album is a consistently strong, musically diverse, and remarkably honest listen, which firmly justifies all the self-lionizing. And not only does the album feature Jay-Z's signature tune, it also spawned arguably the most revered mash-up in music — and, among many other feats, inspired a generation of MCs with its slick lyrical flow and ground-breaking beats. 

Twenty years on, take a look at eight ways in which Jay-Z's faux-farewell changed the hip-hop game.

It Spawned The Most Famous Mashup Album Ever

Jay-Z practically invited the DJ crowd to put their own spins on The Black Album toward the end of 2004 when he reissued the LP without any beats. Pete Rock, DJ Bazooka Joe, and original contributor 9th Wonder all accepted the challenge. But Danger Mouse, aka one half of soon-to-be chart-toppers Gnarls Barkley, had already taken it on, fusing the rapper's original rhymes with music from another colorful record, The Beatles' White Album.

Bringing two pop cultural behemoths together for the first time, The Grey Album (see what he did there) inevitably became a sensation, with EMI's efforts to withhold its release only adding to all the hype. Both Hova and Paul McCartney, however, gave their blessing, with the former telling NPR, "I think it was a really strong album. I champion any form of creativity, and that was a genius idea to do it. And it sparked so many others like it."

It Put Several Key Names On The Map

Jay-Z was no stranger to giving future hip-hop heavyweights their big breaks; both Swizz Beats and Kanye West were virtual unknowns when they contributed to Vol. 2... Hard Knock Life and The Blueprint, respectively. And The Black Album was no different.

Production team The Buchanans, who'd later work with Lupe Fiasco, Amerie, and Dr. Dre, gained their first official credit on "What More Can I Say." John Legend was still a year away from GRAMMY-winning breakthrough Get Lifted when he co-wrote "Encore." And "Threat" helped rap professor (yes, that's a real thing) 9th Wonder to establish himself as a genuine hip-hop authority.

It Produced His Defining Track

Jay-Z had scored, and would go on to score, much bigger hits than "99 Problems." In fact, 24 of his solo singles have charted higher than its No. 30 peak on the Billboard Hot 100. And it isn't always considered to be his best, either: "Big Pimpin'," "Dead Presidents II," and "Where I'm From" all kept the Rick Rubin production out of the top three in Rolling Stone's recent all-time Hova list. Even so, "99 Problems" still has the clout of an undeniably defining tune.

It's been referenced by everyone from Iggy Azalea to Barack Obama. It gave Jay-Z the first of his four Best Rap Solo Performance GRAMMYs (Mark Romanek's controversial monochrome video also picked up four MTV VMAs). Its themes of racial profiling, police aggression, and gentrification led Jack White to hail it as the modern "story of America." And although Ice Cube said it first, it was undoubtedly Jay-Z who put "I got 99 problems, but a b— ain't one" firmly into the hip-hop lexicon.

It Birthed Rap-Rock's Greatest Crossover

Jay-Z certainly wasn't the first hip-hop act to forge an unlikely rock connection. Run-D.M.C.  broke down barriers (literally) in the video for their iconic 1986 Aerosmith collaboration "Walk This Way." The '90s saw collabs from KRS-One and Crazy Town ("B-Boy 2000"), Method Man and Limp Bizkit ("N 2 Gether Now"), and Public Enemy & Anthrax ("Bring The Noise"), all of which were met with mixed results. However, the Jigga Man's EP with nu-metalers Linkin Park, 2004's Collision Course, was a different story.

Notching another Billboard 200 No. 1 for both artists, Collision Course proved that rap-rock could be both credible and commercially successful — which eventually helped pave the way for everyone from Lil Uzi Vert to Machine Gun Kelly. And The Black Album was a key part of their success.

Not only did Jay-Z think to do the team-up after seeing the various mash-ups The Black Album spawned, but three of Collision Course's six tracks stem from the LP: "Points of Authority/99 Problems/One Step Closer," "Dirt Off Your Shoulder/Lying From You," and the Best Rap/Sung Collaboration GRAMMY-winning "Numb/Encore."

It's Been Sampled Countless Times

The Black Album is built on samples, from the emphatic big beats of Billy Squier to Russell Crowe's dialog from Gladiator. But such is the recyclable nature of hip-hop, it's also been heavily sampled since its 2003 release, too.

"99 Problems" alone has been borrowed from or covered at least a recorded 79 times, perhaps most famously on Iggy Azalea's verse in "Problem," her No. 1 hit with Ariana Grande. T.I. brought "What More Can I Say" into the top 10 of the Hot 100 after lifting its vocal hook for "Bring Em Out." Hip-hop sibling duo Clipse appear to have been The Black Album's biggest fans, though, having taken lines from "Public Service Announcement" and "Threat" on "Number One Supplier" and "Where You Been," respectively.

It Pioneered The Hip-Hop Concert Movie

Long before his other half Beyoncé unleashed Homecoming, Jay-Z proved that the concert movie didn't need to be the sole preserve of white guitar acts. Five years after his collaborative Hard Knock Life tour was captured for posterity on Backstage, the rapper invited another camera crew to document what was supposed to be his live swansong. "The undisputed heavyweight champion of the world in hip-hop," welcomes ring announcer Michael Buffer at the start of Fade to Black. And Jay-Z more than justifies such a billing in a dazzling, star-studded set that leaves the 19,000-strong Madison Square Garden crowd hanging on his every word.

Just as compelling is the behind-the-scenes footage of The Black Album's inception, particularly Timbaland and Pharrell Williams' excitement at conjuring the perfect beats. From J. Cole (Forest Hills Drive: Homecoming) to Chance the Rapper (Magnificent Coloring World), a whole host of rappers have since followed suit.

It Allowed Jay-Z To Guide Other Superstars

The Black Album might not have been the studio goodbye purported at the time. But before returning with Kingdom Come in 2006, Jay-Z did  spend the following three years adhering to The Black Album's retirement theme. The self-imposed hiatus allowed the rapper to explore other creative avenues, expand his brand, and – perhaps most significantly for fans of a certain Barbadian superstar – take the reins of the legendary Def Jam Recordings.

Yes, after being appointed to the position of CEO in 2004 by L.A. Reid, Jay-Z signed a then-unknown Rihanna to the label, reportedly responding to her audition with "There's only two ways out. Out the door after you sign this deal. Or through this window." Ne-Yo and Rick Ross were both also plucked from obscurity by the Jigga Man and sent on their paths to stardom during his three years in charge (Jay-Z remained with Def Jam as an artist until May 2009, when he left to concentrate on his own Roc Nation label.)

It Made Retirement A Marketing Tactic

Although Too Short and Master P had both previously reneged on their plans to call it quits, Jay-Z was the first rapper to truly harness the power of an early retirement. Frequently alluding to the news (see "I supposed to be number one on everybody's list/ We'll see what happens when I no longer exist" on "What More Can I Say"), The Black Album was also accompanied by the aforementioned concert film, a memoir (The Black Book), and ever the entrepreneur, even tie-in sneaker and mobile phones.

Hova insists that he really did believe he was bidding farewell at the time, but there's no denying that the announcement helped to both boost his coffers (The Black Album was his biggest selling 2000s release) and add to his mythology. 50 Cent, Waka Flocka Flame, and Lupe Fiasco are just a few of the major hip-hop names who've since made similar claims before quickly walking them back.

Since his return, Jay-Z has added to his legacy in a multitude of ways. He's released collaborative projects with West and Beyoncé; scored a further five solo number one LPs on the Billboard 200 (including The Black Album's unexpected follow-up, Kingdom Come); and added more than a dozen GRAMMYs to his awards haul. And we've not even mentioned the record-breaking world tours, film production credits, and various business interests (TIDAL, Roc Nation Sports) which have helped him become the world's wealthiest rapper with a staggering net worth of $2.5 billion at press time. While The Black Album would've been a remarkable finale, Jay-Z's decision to unretire remains his smartest yet.

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While Snoop Dogg and Pharrell boast a bevy of chart-toppers across their respective careers, both artists' first No. 1 can be traced back to 2003 thanks to one special single: "Drop It Like It's Hot." The track went on to receive two GRAMMY nominations, Best Rap Song and Best Rap Duo/Group Performance. By the end of the 2000s, Billboard declared it the most popular rap song of the decade.

In this episode of ReImagined, contemporary jazz artist and drummer Kassa Overall delivers a live performance of "Drop It Like It's Hot" from a highway. Overall uses pieces of the song's original iconic production — like its tongue clicks — but ultimately turns it into his own with jazzy improvisation.

Overall's spirited performance is a teaser for what fans can expect on his Ready to Ball World Tour, which kicked off with a sold-out performance in Tokyo on Oct. 19. The trek will see Overall hit 30 cities in the United States and Europe, ending on March 21 in Knoxville, Tennessee.

Press play on the video above to hear Kassa Overall's unique rendition of Snoop Dogg and Pharrell's "Drop It Like It's Hot," and check back to GRAMMY.com for more new episodes of ReImagined.

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