“I’m a new artist, by the way… I don’t know if you can tell by this show,” quipped Drake to a packed house at the New York nightclub SOB’s. It was May 26, 2009, and Toronto’s buzzy native son—born Aubrey Graham—was not yet the most successful artist of the streaming age. Coming off the release of his soon-to-be seminal mixtape, So Far Gone, he was just a somewhat nervous kid making his Big Apple debut.

An eclectic audience that included Kanye West, Bun B, MC Lyte, The Alchemist, Talib Kweli and the chief executive of at least one major-label group wanted to see if the hype was real. Drake was still a free agent of sorts. In June he’d sign with Lil Wayne’s Young Money Entertainment and receive a reported $2 million advance. The following year, his major-label debut, Thank Me Later, would enter the album chart at #1, moving 447k copies.

But on that pivotal night in Hudson Square, it was time for Drake to show and prove. Meanwhile, 864 miles south, in Atlanta, Nayvadius Wilburn was living a double life.

Since recording his first track at 14, the man who would become Southern-rap phenomenon Future had dreamed of being part of A-Town’s burgeoning music scene. All the more tantalizing: His cousin Rico Wade led the legendary production outfit Organized Noize, the team behind Outkast and Goodie Mob.

Back then, Wilburn (rap name: Meathead) was starting to make some noise as a member of Wade’s Dungeon Family crew, but as he plotted his first mixtape, 1000, he was struggling to pay the bills. So he hit the streets and began dealing drugs. “Every day waking up and thinking illegal. All my thoughts was illegal,” he recalled to Fader in 2011. “That’s what I did up until I dropped 1000. [Then] I woke up, like, “Man, I ain’t gotta do nothing illegal [today].’”

Over on the West Coast, Compton MC Kendrick, aka K.Dot, was getting serious about his rapping career. A local standout, he’d caught the attention of Anthony “Top Dawg” Tiffith, who in 2004 had started a neighborhood label and management company, Top Dawg Entertainment. Alongside producer Terrence “Punch” Henderson, Top had built TDE as a safe haven for aspiring talent who wanted a life beyond the streets. Gifted freestyler K.Dot was a perfect candidate.

After a string of underground releases and a co-sign from Lil Wayne, he announced that from now on, K.Dot would record and perform under his real name: Kendrick Lamar. “It was an epiphany moment,” he explained of this fateful decision in a TDE publicity video. “When I woke up, I felt like these people need to know who I am, not just a person out here rapping like every other person in the world.”

By the mid-2010s this trio of rappers stood as the most important hip-hop artists of the decade. Today, Drake, 36, Future, 39, and Kendrick, 35, stand as the hip-hop artists of their generation.

“There was a time when we couldn’t imagine anyone in hip-hop being as powerful as a 2Pac, Biggie or Nas, but years later, there’s Drake, Future and Kendrick,” says Gangsta Grillz mixtape king and Grammy-winning producer DJ Drama, who’s logged studio time with all three visionaries. “Right now, they reign supreme. Like all great artists, they pull you into their worlds when you listen to their music. The connection Drake, Future and Kendrick have with their fans is deeply personal.” And they’ve pulled it off with vastly differing creative approaches.

Drake—the biracial Canadian export who began his showbiz career in the early aughts as an actor on Degrassi: The Next Generation—has molded rap and R&B in his own emo image. His early downtempo, genre-blurring records, the best created with longtime OVO Sound producer Noah “40” Shebib, were a shock to the system for hip-hop purists who saw the newcomer as a soft interloper.

Booked and unbothered, Drake proceeded to set off an avalanche of hits: “Best I Ever Had” (2009), “Take Care” f/Rihanna (2012), “Hold On, We’re Going Home” (2013), “Started From the Bottom” (2013), “Hotline Bling” (2016), “God’s Plan” (2018), “Girls Want Girls” f/Lil Baby (2021), “Jimmy Cooks” f/21 Savage (2022) and “Search & Rescue” (2023). He now stands as the biggest singles artist in RIAA history (184 million single units and counting), breaking the record held by Eminem. He’s also the first artist to surpass 75 billion streams on Spotify.

Future, the most prolific of the Big Three, has been on a blistering pace since the release of his 2012 breakthrough, Pluto. His highlight reel is stunning—eight #1 albums, 16 mixtapes, 153 charting singles and nearly 100 million in RIAA-certified activity. Unlike the forefather of the Auto-Tune movement, singer T-Pain, who used the audio enhancer to give his soulful vocals a dreamy, surreal aura, Future flipped the studio tool to make his hedonistic decrees sonically dirty.

Kendrick burst into the public consciousness with his 2012 sophomore release, good kid, m.A.A.d city, which depicted a young K.Dot coming of age in Compton. It was a nuanced, cinematic portrait of life in the hood. At the time, Kendrick was an opening act on Drake’s Take Care Tour. But within months, he was being mentioned in the same breath as his West Coast idols, N.W.A, Ice Cube, 2Pac, Snoop Dogg, The Game and the man who would become his mentor, Dr. Dre.

Yet the 17-time Grammy winner, Oscar nomineeâ€•for Best Original Song for “All the Stars” featuring SZAâ€•and Pulitzer Prize recipient proved to be even more stylistically free-ranging than his heroes.

When it dropped in 2015, the sprawling, jazz-tinged hip-hop freakout To Pimp a Butterfly brought Kendrick into the heart of Black social consciousness. Its centerpiece, the Pharrell Williams-produced “Alright,” became an unofficial protest anthem for the Black Lives Matter movement, a rallying cry against the police killings of Michael Brown, George Floyd, Breonna Taylor, Ahmaud Arbery and countless untold victims of systemic racism. “Wouldn’t you know, we been hurt, been down before / N-gga, when our pride was low lookin’ at the world like, ‘Where do we go?’” Kendrick reassured his people with this ultimately uplifting statement.

On paper, there couldn’t be a more drastic contrast among these three hip-hop juggernauts, which is why their collaborations over the years have been wildly hit-or-miss. Hearing Drake wax poetic about “bitches twerkin’” on Future’s 2011 “Tony Montana” felt as jarring as Taylor Swift dissing a would-be ex on a City Girls record.

More believable was Drake’s playful appearance on Kendrick’s 2012 love letter “Poetic Justice” (recorded before the pair’s public falling out in 2013). Drizzy even made up for his previous miscues with Future on the duo’s 2015 #1 commercial mixtape, What a Time to Be Alive. This time their chemistry jumped out of the speaker. Drake battles the trappings of fame; Future battles addiction. But it’s not dour; it’s an 11-song “Look, Ma, we made it!” victory lap.

Then there’s Kendrick’s revelatory feature on the 2017 remix of Future’s “Mask Off.” Without him, the snarling, octuple-platinum joyride would still be a ridiculously catchy anthem, Future touting an empire of “drug houses, lookin’ like Peru.” But Kendrick adds much when he skillfully homes in on the glaring dichotomy of this unlikely duo: “How y’all let a conscious n-gga go commercial?”

The rise of Drake, Future and Kendrick did not happen in a vacuum, of course.

With the emergence of streaming sites like Apple Music, Spotify, Amazon Music and Tidal, hip-hop fans were able to connect more directly with their favorite artists. And by the late 2000s, such influential blogs as 2DopeBoyz, NahRight, DJBooth, Fake Shore Drive, OnSmash and Rap Radar were quickly becoming go-to destinations for the latest mixtapes, songs, reviews, exclusives and interviews.

In this brave new world, rappers like our thrillsome threesome, as well as J. Cole, Kid Cudi, A$AP Rocky, Chief Keef, Tink and The Cool Kids, among many others, were bypassing traditional gatekeepers, creating a new hip-hop ecosystem in which artists had more say about how their story and music would be presented to the public.

As writer-turned-manager Tim Larew noted in a 2012 Complex piece lamenting the waning power of the aforementioned tastemaker sites, “Artists were generally more focused on the bigger picture, seeing beyond the moment and identifying how their career could unfold—and fans, via blogs, could experience the journey alongside them.”

Much of that bigger picture meant tapping into lucrative avenues befitting the unprecedented commercial and cultural growth of hip-hop, which in 2018 officially surpassed rock to become the most popular musical genre. Thus Drake, Future and Kendrick were able to translate their larger-than-life creativity to the concert stage.

“Obviously, demand has been pretty spectacular for Drake,” says Ryan McElrath, SVP, North American Touring at Live Nation, which is producing the superstar’s It’s All a Blur Tour summer/fall trek with 21 Savage and has promoted sold-out jaunts for Future and Kendrick. “All three are putting out big records, big songs, and people want to experience that live.”

It makes sense that the triumvirate under consideration is enjoying their most acclaimed artistic and commercial periods during a time when hip-hop shows have become multimillion-dollar extravaganzas. It’s a far cry from 30 years ago, when rap gigs consisted largely of MCs walking back and forth across the stage backed solely by a DJ.

Drake and Future’s co-headlining Summer Sixteen Tour, which took in $84.3 million, featured multiple platforms that merged into one massive LED screen, topped by hundreds of suspended, syncopated glowing orbs, which at times risked sensory overload. 2018’s Aubrey and the Migos Tour was even more audacious, with the stage transformed into a sort of dream landscape, covered in projected images and trippy swaths of Technicolor, a swarm of tiny firefly drones and a yellow Ferrari flying over the audience’s heads.

Kendrick’s comparatively stripped-down 2022 The Big
Steppers Tour was unadulterated performance art. The stage setup resembled a therapist’s office, a thematic nod to his emotionally cathartic Mr. Morale & the Big Steppers. Kendrick rapped in an elevated cube, played piano next to a rhyming ventriloquist dummy and was backed by dancers reacting to
his words like a Greek chorus.

His live rendering of frantic single “N95” unveiled both fiery pyrotechnics and subdued light-piercing shadows as the voice of Oscar-winning actress Helen Mirren guided Kendrick through the 91-date avant-garde spectacle. “That’s all entirely Kendrick’s vision,” says McElrath. “Innovation and new technology have allowed hip-hop artists to deliver a level of performance never seen before.”

Consistent invention, hitmaking and influence have allowed Drake, Future and Kendrick to become avatars of the culture.

Drake, however, does have his detractors. Given his propensity for naming ex-girlfriends in his songs, some critics have called out his ladies’-man-with-a-heart-of-gold persona. Others have joked about his authenticity; an online search will lead you to hysterical write-ups dissecting the many accents and slang used over the years by Canadian Drake, Southern Drake, Spanish Drake, Jamaican Drake and British Drake. He has become, as he’d be the first to admit, a walking meme.

“I feel like I have a polarizing presence,” Drake admitted last December in a Twitch stream hosted by sports-betting platform Stake. “I’m almost a character in people’s movie. Therefore there’s a running dialogue. There are jokes. You’re either the villain to some people or a hero to some people… I’ve always been able to laugh at myself.”

Villain or hero, there’s no denying the role Drake has played in obliterating the line between MC and vocalist. Melodic, lovelorn testimony, pithy, swaggering lyrics and moody production sonics, all hallmarks of the Drake formula, have not only been adopted by his acolytes, they’ve been used as a cheat code for the alternative-R&B set. His influence can be heard in the music of everyone from the late Juice WRLD, Brent Faiyaz and Bryson Tiller to Kehlani, Roddy Ricch and A Boogie Wit da Hoodie.

Future may be the only rapper who can match Drake for sheer ubiquity; his sound and patois are inescapable. When GQ named him “Best Rapper Alive” in 2022, there were some eye rolls. But like Vol. 3-era JAY-Z, the I Never Liked You provocateur has become the patron saint of hip-hop’s cool kids, among them Lil Baby, Lil Durk and NBA YoungBoy.

“I remember when he recorded his verse for ‘We in This Bitch 1.5,’” recalls Drama. “Future literally went in the booth and just straight freestyled off the top of his head. I was thinking, ‘Yo, this guy is going to be the next hook king.’ He was dropping heat in Atlanta. I told his manager, ‘It’s only a matter of time before Rihanna and Beyoncé call.’ And that’s what happened.”

Still, Future’s “sex, drugs and hip-hop” image sometimes overshadows his gifts as a songwriter. “I can hear your tears when they drop over the phone/ Get mad at yourself ’cause you can’t leave me alone,” he coldly tells a distraught lover. Keith Sweat he’s not.

And what happens when you’re expected to do more than “just” write hits? Kendrick had already been hailed as “the voice of a generation” by an all-too-eager press before he became the first hip-hop artist to win a Pulitzer Prize, in 2018 for 2017’s bare-knuckled DAMN., upon which it seemed he was anticipating the knives coming out. “A virtuosic song collection unified by its vernacular authenticity and rhythmic dynamism that offers affecting vignettes capturing the complexity of modern African American life,” gushed the Pulitzer committee. Was the adulation he received from this elite bastion of whiteness evidence of Kendrick’s losing his edge?

He didn’t stick around to find out; instead, he started therapy, became a father and virtually dropped out of sight. When he returned five years later with the gorgeously messy Mr. Morale, it was as if he’d turned on a firehose and unleashed all of his hopes, dreams, anger, anxiety, fears, failures and family trauma.

“I’m a private person,” Kendrick confessed to W Magazine in a 2022 cover story. “I could have cut corners and got flashy with it and worded my words a certain way—nah. I had to be in the rawest, truest form I could possibly be in order for it to be freeing for me, in order for me to have a different outlook and the perspective on people I’m talking to.”

As for the next 10 years, it’s anybody’s call.

In February, on Lil Yachty’s A Moody Conversation podcast, Drake said he’s been pondering “a graceful exit.” But if he’s actually having serious thoughts about retiring, he has a funny way of showing it; two months later, he dropped a previously unreleased collaboration with Lil Uzi Vert called “At the Gates.” Social media lit up over what sounded like a subliminal shot at his one-time friend: “Fake woke n-ggas, fake deep, you ain’t know fame before me.” In fact, Drake’s been engaged in a back-and-forth with Kendrick for a decade, since the Compton spitter’s seismic verse on “Control” (a 2013 promotional single by Big Sean featuring Kendrick and Jay Electronica), on which he challenged rap’s elite for the crown.

In a perfect world, Drake and Kendrick would have already made peace and appeared together onstage, with a beaming Future taking it all inâ€•the three most vital hip-hop artists of their time doing it for the culture. Imagine that.