Keeping with the night's all-star theme, Chance The Rapper, DJ Khaled, Migos rapper Quavo and Lil Wayne delivered a star-studded halftime show at the 2020 NBA All-Star Game tonight (Feb. 16).

Chance, a native of Chicago, where this year's NBA All-Star Game is being hosted, kicked off the halftime show with an energetic performance of "No Problem," a featured track off his 2016 GRAMMY-winning mixtape, Coloring Book. He brought out special guest and collaborator on the original track Lil Wayne, who dedicated a few lyrics to late NBA icon Kobe Bryant and his daughter Gianna who, along with seven others, died in a tragic accident last month (Jan. 26).

Read: Jennifer Hudson Delivers Touching Tribute To Kobe Bryant At The 2020 NBA All-Star Game 

DJ Khaled and Quavo then partied onstage next to Chance, performing their collaborative track "I'm The One," featured on Khaled's 2017 album, Grateful. 

The show marks another major televised performance from DJ Khaled this year. Last month at the 62nd GRAMMY Awards, the DJ/producer joined an all-star lineup, featuring John Legend, Meek Mill, Kirk Franklin, Roddy Ricch and YG, to remember late rapper and activist Nipsey Hussle, who was fatally shot last March. 

Chance closed out the jam-packed halftime show with a moving tribute to Bryant. Emotionally distraught, he performed "I Was A Rock," a tribute song he originally performed in memory of late boxing legend Muhammad Ali at the 2016 ESPY Awards show, as images and videos of Bryant played on a screen behind the rapper. 

The halftime show closed out the stacked musical lineup at the 2020 NBA All-Star Game and Weekend, which included performances from: Jennifer Hudson, who paid tribute to Bryant; Chaka Khan, who sang the national anthem to officially open the game; and Queen Latifah, who covered Stevie Wonder.

Read: Watch Chaka Khan Sing The National Anthem At The 2020 NBA All-Star Game

Other artists who performed and appeared throughout the weekend include Common, Chance The Rapper's brother and fellow rapper, Taylor Bennett, Megan Thee Stallion, Normani, Jeremih and others. 

Queen Latifah Delivers Soulful Performance Of Stevie Wonder's "Love's In Need Of Love Today" At NBA All-Star 2020 Weekend

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

With Thanksgiving around the corner, this New Music Friday offers us a feast of new sounds from some of the music industry’s biggest artists.

Country star Maren Morris teamed up with Teddy Swims for a passionate duet version of his song "Some Things I'll Never Know," while Steve Aoki & ERNEST paired up for an energetic dance/country crossver, "Us," from Aoki’s HiROQUEST 2: Double Helix.

American band Bleachers unleash their wild side with "Alma Matter," from their upcoming self-titled album dropping March 8, 2024. Meanwhile, alternative rock band Bad Suns released their catchy, six-track EP Infinite Joy. Across the pond, long-time British rockers Madness released their 13th album, Theatre Of the Absurd Presents C’Est La Vie.

With sultry sounds from R&B songstress Ari Lennox to mellow, indie rhythms from Dermot Kennedy to upbeat, radiant vibes from the duo Surfaces, this Friday brings a kaleidoscope of sounds from across every genre. 

Along with the slew of releases mentioned above, press play on releases from the likes of André 3000, Drake, Ozuna, Lil Wayne and 2 Chainz, Danny Brown, and Bibi and Becky G — and be sure to add some new sounds to your rotation.

André 3000 - New Blue Sun

If you’ve seen Andre 3000’s impromptu flute performances in the past few years, then the GRAMMY winner's new sound won’t come as a shock. On his eight-track debut solo album New Blue Sun, the Outkast member experiments with wind instruments and percussion, creating serene and melodic compositions.

Across eight elaborately titled tracks  — "I swear, I Really Wanted To Make A "Rap" Album But This Is Literally The Way The Wind Blew Me This Time" and "That Night In Hawaii When I Turned Into A Panther And Started Making These Low Registered Purring Tones That I Couldn’t Control… Shyt Was Wild," — Andre details his artistic journey and the possibility of returning to rap music. Because, as Andre has told numerous outlets, New Blue Sun is not a rap album.

"I get beats all the time. I try to write all the time. People think, Oh, man, he’s just sitting on raps, or he’s just holding these raps hostage. I ain’t got no raps like that," he told GQ. 

In the future, fans might see 3000 return to the rap universe but in the meantime, let’s enjoy the ambience of the blue sun. 

Drake - For All The Dogs Scary Hours Edition

It’s not Scorpio season without a release from the scorpion king himself, Drake. In the latest installment of his Scary Hours series, Drake brought in a heavy-hitter lineup of producers including Lil Yatchy and Alchemist.

With songs surrounding themes of betrayal and broken trust (an the less-than-subtle chant "F— My Ex" more than 10 times in one song), For All The Dogs Scary Hours Edition shows how deep the Certified Lover Boy is in his feelings.

Drake brings out his Swiftie side in the track, "Red Button," shouting out Taylor Swift with lyrics "Taylor Swift the only n—- that I ever rated/ Only one could make me drop the album just a little later/ Rest of y’all, I treat you like you never made it." Seems that the big-ups and grudges heard on October's For All The Dogs translate to Scary Hours, too.

His song "Evil Ways" features J. Cole, increasing anticipation for their joint tour, which was announced on Nov. 13.

Ozuna - Cosmo

After receiving a nod for Best Reggaeton Performance and performing with David Guetta at the 2023 Latin GRAMMYs, Puerto Rican Singer Ozuna dropped his sixth album, Cosmo. Filled with soon-to-be dance floor staples, Cosmo highlights Ozuna's versatility.

Songs like "El Pin" and "La Chulita" are full of infectious dance and Afrobeats influences, yet stay true to his reggaeton roots. The 15-track record also includes collaborations with Jhayco, Chenco Corleone, Anuel and David Guetta.

"When you think of a colorful image, you think of youth. When people listen to this album, I want them to take it seriously," Ozuna said in an interview with the Fader. "People want to hear what’s real, what’s clear-cut, in black and white.”

The goal, he continued, is to allow "people to know who the real Ozuna is."

2 Chainz, Lil Wayne - Welcome 2 Collegrove

Lil Wayne and 2 Chainz have joined forces once again to release their second joint album, Welcome 2 Collegrove. The album’s title is a melding of 2 Chainz's hometown of College Park, Georgia, with Lil Wayne’s Hollygrove, Louisiana.

Welcome 2 Collegrove includes features from a cross-section of hip-hop and R&B greats, including Usher, 21 Savage, Rick Ross, Benny The Butcher and Fabolous. Tracks like "Presha" and "Long Story Short" bring back the duo’s classic rap sound from their 2016 project COLLEGROVE, and show their ability to create hip-hop anthems. The special guest artists add even more depth to their songs. 

Danny Brown - Quaranta

After a four year break, Detroit rapper Danny Brown is back with his seventh album, Quaranta. A departure from his earlier, more club-centric music, the 11-track album offers a new perspective in Brown’s life.

Quaranta is a turning point in Brown's musical journey, where he reflects on themes of regret, self-destructive behavior, and growth. While songs like "Ain’t My Concern" and "Celibate" still include his signature flair of fast, high-pitched verses, this album takes on a more mature and introspective route. 

Bibi feat. Becky G - "Amigos"

On "Amigos," South Korean singer Bibi teamed up with Latin star Becky G for a multicultural but ever-relatable track that focuses on being hung up on past lovers despite having someone new in their life. "I know we had a good time and that you always want more / But if my boyfriend calls, we’re just friends, nothing more," they sing in Spanish.

"Amigos" is rife with hip-hop influences — a genre Bibi loves. 

"Expressing oneself through lyrics is so real and genuine," BIBI told AllKPop. "As I’m someone who wasn’t necessarily gifted with natural musical talent — I didn’t even know the difference between boom bap or trap beats until way later. I think the other factors of music organically followed as I grew as an artist."

15 Must-Hear Albums This November: Dolly Parton, Jung Kook, Marshmello & More

The 2017 GRAMMYs were certainly a life-changing evening for Chance the Rapper. The hip-hop star walked into the ceremony with a whopping seven nominations and took home three golden gramophones, including Best New Artist and Best Rap Performance for his single "No Problem," featuring Lil Wayne and 2 Chainz.

In this episode of GRAMMY Rewind, revisit the moment Chance the Rapper took home his third win of the evening for Best Rap Album for his mixtape Coloring Book. 

"I didn't think that we were going to get this one, so I don't have cool stuff to say this time," he quipped as he hit the stage alongside his former manager Pat Corcoran and music director Peter CottonTale.

Chance began by expressing his appreciation to God "for everything He's ever accomplished for me" before showing love for his family and friends.

"This is for every indie artist — everybody who's been doing this mixtape stuff for a long a— time," the rapper exclaimed. "Shout-out to Soundcloud for holding it down. It's another one, baby!"

Press play on the video above to watch Chance the Rapper's gracious speech for Best Rap Album at the 2017 GRAMMY Awards, and check back to GRAMMY.com for more new episodes of GRAMMY Rewind.

50 Artists Who Changed Rap: Jay-Z, The Notorious B.I.G., Dr. Dre, Nicki Minaj, Kendrick Lamar, Eminem & More

When Westside Gunn refers to himself as "the king of the underground," it's not hyperbole. The veteran rapper has spent the last decade-plus providing hip-hop with a streetwise, neo-boom-bap style that echoes heavily in the music of today. And as the founder of independent hip-hop label Griselda (and its related rap collective), Gunn's influence is felt through stars like his brother, Conway the Machine, his cousin, Benny the Butcher, and the enigmatic Mach-Hommy. 

But Gunn considers himself more a curator than a musician. He is obsessed with fashion and high art, more prone to mention going to see opera or buying a painting than jumping into a rhyme cipher.

All of Westside Gunn's obsessions come together on his new album And Then You Pray For Me. The rapper is positioning the project as a sequel to his 2020 LP Pray For Paris, which was inspired by Gunn attending a Paris Fashion Week runway show as a guest of the late Virgil Abloh. Abloh was the art director for both albums, which feature figures from iconic artworks laden with Gunn's signature chains; And Then You Pray For Me uses both the Mona Lisa and Caravaggio's The Entombment of Christ. 

While the 21-track album features plenty of Gunn's trademark neo-boom-bap sounds, he updates things a bit by including some songs that have a trap music influence. It contains stellar guest turns from old friends like Conway, Benny, Stove God Cooks, Rome Streetz, and Boldy James. But there are also surprising appearances from artists you might not normally associate with Griselda — Jeezy, Rick Ross, Denzel Curry, and Ty Dolla $ign.

Gunn has recently referred to And Then You Pray For Me as his last album, but don't expect him to slow down. He's making movies, planning big moves in the fashion world, and continuing to guide the careers of other artists. 

GRAMMY.com caught up with Gunn as he was, naturally, shopping in New York City's SoHo neighborhood ("I'm over here on Mercer [Street], so it's Lanvin, Balenciaga, Marni, Bape — it's all right here," he boasts). We discussed his creative pairing with Abloh, why he's really a curator at heart, and his views on underground rap's evolution over the past decade. 

The conversation has been edited for length and clarity.

Not to start on a super serious note, but as I was preparing for this conversation, I realized that we just passed the 17-year anniversary of the murder of your cousin, rapper Machine Gun Blak. If he could see you now, and if he could hear the new album, what do you think he might say?

First of all, he'd be all on [the album]. But he'd be super proud, man. Even when he's not here, he's one of my biggest fans, I feel like. His energy is Westside Gunn. Westside Gunn is a perfect example of Machine Gun Blak — just the raw, the grittiness. The grimy part of Westside Gunn, that's Machine Gun Blak. That's his spirit.

But I think he would love this album. It's a great piece of work. It's my favorite that I ever worked on. Out of all my projects ever, this is the most fun I ever had making one. 

Does it feel like it's been 17 years since he died?

Nah. It doesn't seem like 17 years, honestly. And it's crazy because I just went to his grave site. I remember [the day he died] like it was yesterday. I vividly remember that day — what was going on, what I was doing, where I was going, everything.

Where were you when you found out? 

See, back in those days, that's when we were still in the streets. So I was just about to go make a move. I was talking to him on the phone, and I was like, "I'll hit you when I get over to Atlanta." Because at that time, I was making moves. That's before all of this. It's the things I rap about now. When you hear the lyrics, these are those days. 

He called me, and it was a situation. He was talking about it, and I was like, "Sorry to cut you off, but I gotta go handle this. When I get there, I'll hit you back so we can finish talking about it."

At that time I was still catching the Greyhound from Alabama to Atlanta. But it was crazy because I missed the bus, and I never miss the bus. So I was on my way back to the house in Alabama, and my grandma called me.  

This era of your career, which this album is a cap to, began in 2012 when you realized you had to step up and be an artist because Conway The Machine had gotten shot and you weren't sure he'd be able to rap anymore. I've always been curious about your state of mind at that moment.

Even then I was still in-the-streets Gunn. We was working so hard, man. I was acting as his manager and investing my bread, my time. I really wanted Conway to be the biggest artist in the world. Unfortunately, when he got shot, it was a devastating blow.

Of course, that's my brother. That's the number one thing. And it was also like, the streets is crazy. I thought, I'm a smart guy. If I just put in my effort, I could really make this happen. At that time, I was really in the streets, and I felt like the [other] rappers weren't. It was like, you're really rapping about us. 

It was that kind of mentality — that if I come in this game, can't nobody touch me, because I'm as real as it comes. I just put my hustle skills from the streets into this, and it all worked out. 

During the heyday of that era of Griselda, you guys released a flood of projects — dozens and dozens of mixtapes and albums. 

It was a flood. It was the craziest flood since No Limit [Records].

What was a typical day like for you when all that was going on, circa the mid-2010s?

Just being at [producer] Daringer's house. Getting high, eating f—in' Franco's pizza, drinking Loganberry, and Daringer cooking the craziest beats you ever heard in your life. The rest is history. Just having fun, man. Everybody had they hustles. Believe it or not, even Daringer was hustling! We from Buffalo, man.

You've always been someone who understood the importance of branding. Even on early Griselda projects, you'd promote GxFR [Griselda by Fashion Rebels, Gunn's clothing line at the time]. 

Yeah, because that's the thing: Griselda Records comes from Griselda by Fashion Rebels. I had the clothing brand first. I was already doing a clothing line and it was just like, What am I going to name this record company?

I've always been into fashion. I actually do more fashion-related things than hip-hop-related things. I'm a true designer. I've been designing since I was a kid, and that's the thing that I want to get into more. 

I've been rhyming since '12. That's over a decade. If we're looking at NBA years, NFL years, I'm already a super-vet. I'm not trying to be one of them dudes that went from averaging 40 a game to now I'm averaging five, looking crazy and old. 

I know when to gracefully bow out. And I know I'm coming to the end. I don't want to keep rapping forever about the same things, because in my life I'm maturing. I'm doing other things. I'm collecting art. I'm going to see operas. 

But it's not the end right now. Right now, I just want to give people the best music. And I also want to let people in. I've been doing these [YouTube] episodes for this album where I've been letting people into my life for the first time in my career. Everybody has been loving it. 

For the first time, people are actually getting to see the inside of Westside Gunn's life. I think that's one of the things that I lacked on, was letting people in. If I would have let people in a long time ago, I'd be way bigger. But everything is about time, and I'm not tripping.

Before I hang up the mic, I still want to kind of give you a journey with the music. This new project, it's a super different vibe. I've never made an album sound like this. It's the perfect art piece that I could have possibly created.

It's just the space I'm in in life. It comes with maturity — traveling the world, kids getting older, things like that. You can hear the music has matured. It's still raw though. That's the thing about me. I'm still gonna give you that Griselda Westside Gunn. That's never gonna change. I'm not going too far out of context. 

For this album, you've introduced the alter ego "Super Flygod." What does that name mean? 

Listen, man, Super Flygod right now is talking to you with a ponytail. I'm on another level. Super Flygod is what I've always been, but times 10. I'm super bougie. I love five-star meals. I love five-star hotels. I love wearing $10,000 outfits. I love getting massages. I love smelling good. I love just looking good. That's Super Flygod. 

It's just a different energy. It's something the game never seen before. I did the unthinkable at least 100 times already. I'm still doing it. 

What was it like for you to see Conductor Williams — a producer who has worked with Gunn and Griselda for many years — land a single on a Drake album?

Beautiful. That's what we do it for. He did exactly what he was supposed to do, and that's be on the No. 1 album in the world. He deserves all of that. That's what we're in this game for — to be able to leave a legacy and take care of our babies. So for him to be on the No. 1 album, that's a super blessing. 

That's the thing about Conductor — it's just gonna be the beginning. He's on my new album a few times. So he's gonna have a hell of a month. It's the biggest month of his life. Business is booming for Conductor. 

You've used the word "curation" a lot over the course of your career, and especially in regards to this album. What does that word mean to Westside Gunn?

First of all, that's my favorite thing to do on an album. Curation from me is me. I can curate for you, I can curate for MC Hammer. It's you, but it's me. 

When I curate a project, that's me naming every song, that's me picking every beat, that's me doing the sequence, that's me making the art cover, that's me doing the merch. You see what I'm saying? It's you, but it's me. All you're doing is showing up and rapping. That's all you gotta do.

Virgil Abloh is credited with art directing this album's cover. What did that mean, specifically? 

When I went out to Paris [for Paris Fashion Week in 2020], I really wasn't going to make music. I just felt the energy from Virgil having me out there. When I hit him and told him it was done, it was just like, "There's only one person that can do this cover." It had to be him. 

Virgil was an icon. So to have Virgil cooking up for you is already legendary. This don't happen to nobody from Buffalo, man. But when he was cooking, he was making me multiple pieces. At first, the idea was, I'm gonna do a trilogy [of Pray albums]. I was gonna have the Mona Lisa be the picture that represents all three of them together. I was thinking [of a] box set, with a Mona Lisa front and three different covers inside. 

Once he passed, it changed what I wanted to do with it. But we were already talking about dropping [a second Pray album]. We were already going to re-release the first shirts we did, and I was going to do new ones. But when [his death] happened, I put everything on a standstill and I didn't really know how I wanted to approach it again.

It was like, Damn, should I do the trilogy, or should I just make it a part two? I had different options. At the end of the day, it was just like, I think I'm just going to finish it up. I really want to give the people the work we created together before I throw in the towel. I felt it was only right. That's something that I want the world to always see and remember — what me and him cooked up together.

You say in your new YouTube documentary series that this new album will probably go over people's heads. What aspects of it do you think people might not get initially, or take a few years to catch up to?

The same reason why they're catching up now to the s— that I was doing five years ago, and everybody acts like it's new. I've always been ahead of my time. Always. I probably get copied off of the most in the industry. But you see that I've always gotten respect from everybody: from the Drakes, from the Tylers, the Rockys, Kendricks, Coles, anybody. I'm a one-of-one. It's never been seen before. 

The respect I get, it could be on a mainstream level, but then I could still be on an underground level. I can do something with an Estee Nack, but then turn around and do a song with Mary J. Blige. That's who Westside Gunn is. I got songs with everybody you can possibly think of, rhyming-wise or production-wise. All the legends, even our fallen legends. I can't even think of no other emcee that got a record with Sean Price, Prodigy, DMX, and MF DOOM. It's impossible to name another one. 

Westside Gunn is so cultured, people don't even understand. That's what I mean about [being] over people's heads. People still don't even get it. They're scratching their head, like, "How is this guy on [Kanye West's] Donda? How is this guy on [Travis Scott's] Utopia?"

There's a big part of underground rap now that can be traced directly to what Roc Marciano began doing in 2010, and what you guys started doing just a few years later. What do you think when you see a lot of your aesthetic from that time in the current underground scene?

The current underground scene, I'm loving it. Because you gotta think — at that time, like you said, it was only really Roc Marci, Action Bronson — a couple heads. That's in the space that we come from. Of course, we still had the J. Coles and Big Seans and all that, but that was another lane. We're in the same neighborhood, two different streets. 

But on our street, people on the block was Roc Marci and Action Bronson. Danny Brown, he lived on the block. People like that. When I came on the scene, that's all it was. But I took the bull by the horns. Like I said, I'm a hustler. I was still hustling in the street. I had a hustler mentality, and once I told myself I had to quit cold turkey, I never looked back. I just went extra hard. 

With the new heads, I'm proud of them. At the end of the day, I'm happy that I was able to be somebody that they could study. That they could see these vinyl deals or how this merch is played — I'm kind of like the blueprint. I'm not going to say I'm the king of the underground, but I'm the king of the underground.

Even though I'm the king of the underground, I'm still on Donda. I'm still on Utopia. I'm still making all these big songs and these big records. And even yesterday, we put up the Post Malone clip saying if he could work with anybody, it'd be me. 

I'm the one that put the most points on the board, in every way possible. But this is also showing the new heads, If I could work hard, I'm gonna be the next Roc Marci, I'm gonna be the next Action Bronson in that space.

What is the possibility of getting the original Griselda trio of you, your brother and your cousin back together for a project? 

That's coming in '24. You don't even you got to ask twice. That's already done, my brother. 

A Guide To New York Hip-Hop: Unpacking The Sound Of Rap's Birthplace From The Bronx To Staten Island