Big Sean can easily imagine an, even more, bizarro reality. In this scenario, he never freestyles for Kanye at that radio station in Detroit and never signs to G.O.O.D. Music. He doesn’t invent hashtag rap or collaborate with Nas, Eminem, or Lil Wayne. There are no platinum plaques. There aren’t two No. 1 albums. He doesn’t drop 10 singles that crack the Billboard Top 40 or accept trophies from BET or MTV. Someone else nabs those four Grammy nominations too.
Sean Anderson certainly wouldn’t be at Drai’s Nightclub for a special Drai’s Live Residency on a broiling May Saturday night, rapping on this rooftop aerie overlooking the neon archipelago of the Las Vegas strip—before a frenzied and swaying audience of 4,000 adoring fans who have memorized every syllable.
Being a professional rapper was all Big Sean ever wanted to do, and now he’s one of the most famous rappers on earth. Oh, and he dates Jhene Aiko—who he describes as a cross between Aaliyah and Sade. Who am I to contradict him?
But every time Sean squints, he glimpses the alternate route: a conventional 9-to-5 job anonymously toiled at for a half century, the disappointed wife, the litter of kids who lacked a proper role model—the quiet desperation that Thoreau lamented. Big Sean might not have written Walden, but he did write “I Don’t Fuck With You,” which takes a different route to achieve similar ends.
Lingering neuroses about that thankfully bypassed outcome concerns much of his latest album, February’s Gold-certified, I Decided. It opens with an elderly voice lamenting a wasted life. It concludes with a life-affirming conversation between Sean and his mother, celebrating his ability to elude deadening existential complacency.
“For a few years now, I’ve really felt that this was my second chance to get it right,” Sean says in a luxury suite at the Cromwell, the hotel attached to Drai’s.
“For a few years now, I’ve really felt that this was my second chance to get it right.”
There’s a pool table and many leather-bound books. A flat-screen seemingly as big as a city block. Sean wears a yellow Ice Cream long sleeve shirt bestowed to him by Pharrell as part of the brand’s re-launch. He’s rocking torn blue jeans with zippers and black floral insignia’s, and diamond earrings glistening bright enough to be donated to the Las Vegas Neon Museum.
“The conceptual inspiration came from a conversation with one of my friends. One late night in the studio, it motivated me to finish the song we were working on,” Sean continues. “The next day he told me how much it had stuck with him—that idea that we’re reincarnated and this life is our chance to perfect things.”
If Big Sean’s success has taught us one thing, it’s the power of persistence. At the time that you are reading this sentence, there are approximately 2,523,243 aspiring rappers in the United States. Despite their best attempts to get you to check their Soundcloud, nearly all will fail. Under no circumstances was Big Sean willing to accept the potential “L.”
In arguably the most impressive ambush in rap history, the then high school junior ran up on Kanye at Detroit station, WHTD. Sean had regularly appeared on their late night freestyle sessions and easily convinced the security guard that he’d left his phone behind. Once inside, Sean begged Kanye to give him a chance. Kanye explained that they were too busy, but nevertheless, Sean persisted.
On the way to the parking lot, Sean leveraged 16 bars into 10 minutes of Kanye’s time into a 10-year career (and counting). But that opportunity didn’t manifest for several years, so Sean matriculated at Michigan State and was forced to contemplate normalcy. Consider how you would handle that situation. Most of us, even if we somehow briefly wowed one of the most iconic rappers of all-time, would chalk it up as an aberration. Maybe we’d dismiss it as Kanye merely being polite. Instead, Big Sean kept hitting up his mentor until there was a deal on the table.
“I’ve felt counted out since grade school,” Sean traces his resilience. “Rap is a competitive art form, but this is how I’ve always been. Even when I was running track in school, I wanted to be the fastest.”
Take his latest double-platinum smash, “Bounce Back.” On the surface, it’s a Metro Boomin produced club banger, but the bars convey the philosophy that’s carried him to this point. Every minor setback precedes a major comeback. There was a nearly four-year lacuna between Finally Famous: The Mixtape and Finally Famous: The Album. In that interim, skeptics derided him as a mixtape rapper, a Kanye protégé incapable of landing a mainstream single. Then he silenced critics with three Top 40 singles, including the triple platinum, “Dance (A$$).”
Sean is slightly groggy after having just woken up from a quick nap on the flight from Van Nuys, California, to Las Vegas. He’ll return home right after the Drai’s show to his 4,500-square-foot, five-bedroom, mock-Mediterranean estate filled with arcade games, abstract paintings, and a Big Sean slot machine.
The platinum album he’s alluding to was 2015’s Dark Sky Paradise, where Sean directly confronted the death of his grandmother, his tabloid breakup with Naya Rivera, and subsequent relationship with Ariana Grande. A thoughtful consideration of his Detroit roots, his place in the world and the pop firmament at large. Complex named it the sixth best album of the year, hailing it as “wonderfully plainspoken, impassioned, and dynamic.” In our conversation, he mentions that he’s already at work on the follow-up to I Decided—plus another undisclosed project that he can’t discuss.
“As artists, we sacrifice our personal lives, our story, our everything,” Sean says. “If you listen to my songs, you know that my grandma died and that she was a Captain in World War II and one of the first female black police officers in Detroit. You know about my mom. You know who I broke up with…you know it all.”
The rapper-as-motivational figure has been with us even before Outkast told us to “get up, get out, and get something,” but Sean’s connection with fans is practically umbilical. Whether you love or hate him, it’s hard not be struck by his unstinting positivity and optimism. The ethos can get almost evangelical at times, but he’s spent a substantial portion of his time and energy to make that attitude more than lip service.
Run by his mother, the Sean Anderson Foundation partnered with Adidas to build a state-of-the-art studio at his old high school. They’ve also created a Mogul Prep program, in which music industry professionals visit Detroit High Schools to tell their stories and various secrets of surviving and thriving in the business. Sean readily admits that not everyone graduates to getting six figures a show, but there’s an array of music-related jobs available from publicist to stylist, manager to video director.
We talk for a few more moments about the future. About how he sees himself as someone with a long way to still go, someone who continues to have a ton of untapped potential and refuses stasis. You understand why he made it this far. Even at a career zenith, he’s relentlessly dedicated to self-improvement.
“I want to be remembered as someone who stood for something… someone who did right by the city, who gave back,” Sean says. “Someone that people didn’t expect to go as far as he did—that makes the story even better.”
Then the publicist flashes that unmistakable “wrap it up” hand gesture. It’s time for the Drai’s performance. Sean shakes off the last bit of exhaustion and slowly ambles out the door, down the elevator, downstairs to the deafening crowd. He plays the hits, one after the other, including “Blessings,” which might as well be a personal mantra. Few are this fortunate, even fewer are so appreciative.
“As artists, we sacrifice our personal lives, our story, our everything.”
The set winds down and as if on cue, he pauses for a second, the tufts of smoke temporarily clearing, the confetti having stopped falling from the rafters. If there’s a point he’s trying to convey, this is obviously it.
“Life is about taking risks,” he tells the audience, who grow briefly silent. “That’s what it’s all about. You have to fail to eventually succeed. I’m just telling you from my experience. If I wasn’t sharing it with you from the stage, then I’d feel like I wasn’t living up to my potential.”
Then he raps “Bounce Back” and the crowd detonates once more and I suspect that at this moment, there is no other scenario that he could really imagine.