The conquering underdog archetype is tailored to hip-hop’s visceral emotional range with the same precision as a made-to-measure Savile Row suit destined for a James Bond film. “You counted me out and I came back better than ever” is a recurring sentiment that is older than the genesis of hip-hop itself, though contemporary rappers seem to have perfected the “started from the bottom, now we’re here” narrative. Few recent projects have channeled an attitude of righteous reprisal and ultimate triumph in as vehement a manner as Big Sean’s fourth studio album, I Decided. It’s another step in the evolution of the Detroit talent — a definitive statement from a relatable dark horse who has finally won the race.

“I try to meditate on a daily basis. Sometimes I don’t get a chance because I’m running as soon as I wake up but it’s definitely a way I lift my mood and stay connected to my spiritual self,” says Big Sean with no trace of pretension. The practice isn’t driven by New Age mysticism or the modern appropriation of some obscure ancient religion turned West Coast fad, or even legal complications that miraculously led to a flash-bang moment of clarity, as fellow celebrities like Lindsay Lohan, Paris Hilton and others have conveniently experienced. For Sean, the goal is to momentarily mute the demands of a fast-paced life and find a fleeting sliver of normality. Home — a familiar bed worn in from nightly use, the monotony of a daily routine, even a scant few moments of personal time — has become a foreign concept for Sean ever since he catapulted from voraciously determined Detroit teen to finally famous; the upgraded state of being the rapper joyfully reveled in on his debut studio album of the same name.

Sacrifice and feeling underestimated, on the other hand, have become habitual, almost even ritualistic in their correlation with Sean’s success. Both are themes he’s revisited often, communicating the relationship between sacrifice, success and loss in lyrics that chart the spectrum of human emotion. In “Once Bitten Twice Shy” he laments that life has become too hectic to visit his beloved grandmother, stating, “Man I miss my grandma, she ain’t passed away or nothin’ I’m just busy on camera / I love her, I love her, I should call her up and tell her.” While it’s a simple enough admission, crafted into a rudimentary enough verse, there’s a naked sensitivity that’s a departure from the braggadocio and pageantry of today’s popular rap music.

Similarly, “Blessings” revisits the recurring idea that fame seems to find a way to insidiously fracture even the most intimate relationships. “This is that late night working after three, man / This is why my old girl was mad at me / This is why I’m your majesty, man,” Sean raps before revealing, “My grandma just died, I’m the man of the house / So every morning I’m up because I can’t let them down, down.” The overarching theme of divine favoritism tempers the song’s mercurial production while the lyrics embody the kind of difficult but ultimately relatable decisions that make Sean accessible to such a diverse fanbase. “I pledged to put my life experiences, my successes and ‘quote, unquote’ failures, and just anything I’m going through, on the line. That’s what people relate to and I feel like. I hope it helps them out. I hope they can listen to my music and take something from it in times where inspiration is needed,” says Sean.

Big Sean’s music doesn’t necessarily offer the kind of complex metaphor and meticulous storytelling of Kendrick Lamar, or the irresistible, trap-centric pull of 808s, snares and energetic ad libs that Migos have made their own. Instead it hits a more universal note — that of the regular guy who finally made good. There’s certainly still a healthy dose of the standard flexing, but that’s to be expected. Mentions of gluteally blessed women, expensive jewelry, designer clothing and taking care of the day-one crew are as standard as avocado toast is to a Williamsburg brunch menu. Despite buying into more than a few common rap tropes, Sean still manages to maintain a down-to-earthness and affable quality that is reachable. “I got the streets and I don’t got no felonies,” he peacocks on “Sacrifices,” casually offering an alternative to the presiding narrative of rappers engaging with the streets in the context of survival, violence, respect, money, power, or a conflation of all of those things. This ability to channel popular ideas in what mainstream America often still refers to as “urban” music, and repackage them in a way that doesn’t feel too niche, or make protective suburban mothers feel leery, is a skill that many of his peers simply don’t possess. When Sean discusses heartbreak, or working more than he sleeps, or even missing his family, it feels a bit banal in its normality. Yet that is what makes his role as a self-proclaimed underdog feel so universal. He didn’t segue from starring on a major television show straight into the rap business like Drake. He didn’t get shot nine times and then drive himself to a hospital, forever cementing his street credibility and fearlessness like 50 Cent. Instead, he was just a normal, hard-working, clever teenager from Detroit, who, through equal parts determination and luck, caught the eye of a music mogul. We’d all like to think that could happen to anyone, and therein lies Big Sean’s appeal.

Sean Michael Leonard Anderson was born March 25, 1988, in Santa Monica, California to James Leonard and Myra Anderson. When he was only two months old, his family relocated to Detroit, Michigan, a city that would shape the young performer’s worldview and eventually put him in front of his future mentor, Kanye West. Raised by his schoolteacher mother and grandmother, on the city’s beleaguered West Side, Sean’s childhood was underpinned by a familial commitment to education. From kindergarten through eighth grade he attended Detroit Waldorf, one of the best schools in the city, and the only remaining independently private academy left in Detroit today. He then went on to enroll in Cass Technical High School where he graduated with a 3.7 GPA. Like many college prep academies, Cass offered a strenuous, personalized curriculum and an admission system predicated on test scores and grades, rather than neighborhood stratification. Perhaps a testament to the success of the high school’s music program is that Sean is only one of many notable alumnus — Diana Ross, Alice Coltrane, Lily Tomlin and Jack White were all Cass students.

Still, when it comes to musicians, artists and others of the creative ilk, there’s often a perception that their minds are so unique, sensitive or misaligned with reality that traditional learning environments are destined to fail them. It’s a mythology that further removes the creators from the non-creators, and implies that your favorite artist occupies a special world that others cannot access. Kanye West’s now-iconic debut album, The College Dropout flirts with these themes, something that stands in stark opposition to Sean’s own ethos — he has credited much of his success to educational opportunities. That he was specifically educated in Detroit’s school system only adds another layer of relatability to the image he’s developed as the inoffensive but scrappy everyman who knew he was destined for greatness. For years the city’s highly publicized struggles with violent crime, under-served public schools, racial tensions, and a crumbling infrastructure have been headline news and fodder for idealistic politicians, as well as informing the music of high school dropout Detroit rappers like Eminem and Danny Brown. Sean’s quiet investment in Detroit, through his eponymous nonprofit which seeks to directly help the city’s education system, is just the kind of thing people want to see from their entertainment idols. It’s a reminder that he too came from humble circumstances, and that he hasn’t forgotten the people who are still there.

The story is kind of a narrative for me; it’s about how I feel and a lot of the things I’ve gone through. A lot of times I do feel like the older me is guiding me. I think that wisdom really helps me progress.

“Your hometown influences who you are. I feel like Detroit is a city that has been overlooked. It’s a city where people have really had to struggle, but it’s also a city that has seen a lot of success; it’s a place where people are just thankful to get by. Being from Detroit and being black — those two things were big odds for me,” Sean says. “I mean you look at statistics or even what people tell you — it’s like you’re supposed to do one thing or you’re destined to wind up in jail. I remember the first day of school in the assembly they said, ‘Take a look at the person to the left of you, now take a look at the person to the right of you; there’s a 50 percent chance that they won’t be here when you graduate.’”

Granted, a doomsday prophecy is not what hundreds of young minds existing in a city that is consistently portrayed as embroiled in crisis need. Still, the memory empowered Sean to consciously make the choice not to be relegated to a mere statistic in the eyes of those around him. He kept busy by securing a position as the host of a hip-hop show on the now-defunct local station WHTD. The job also gave Sean an opportunity to participate in local showcases and battle rap sessions that helped him hone and nimble the one-word punchline style of rap, coined “Supa Dupa” flow, that he has been credited with pioneering. Years later, friendly interactions with Drake and the popularity of the Canadian rapper’s single, “Forever,” (which features a very similar rhyme scheme) lead to much debate about who actually bit whose flow. Ultimately, Drake credited Sean for being one of the first to utilize the “Supa Dupa” style. In a 2010 interview with AllHipHop he said, “To be honest, that flow, you can trace it back to like… I trace it back to Big Sean. That’s the first guy I heard utilize that flow throughout the duration of a verse. I’ll give him that credit. I think Kanye got it from him.”

In 2005, only a year after establishing the G.O.O.D. Music label, West made an appearance at 102.7 radio in Detroit. Sean was working in telemarketing at the time but was alerted to West’s presence by friends. He immediately went straight to the station, hoping for a chance to meet one of his favorite rappers. After working up his nerve, Sean says he approached West and asked him to listen to an impromptu freestyle. At first the famously moody “Famous” rapper refused, but eventually he acquiesced and a terrified Sean began to rap, directly to the floor. West would later explain that he wasn’t signing new acts at the time but felt impressed enough with Sean’s raw talent that he accepted his demo tapes, and the two kept in contact. Two years later, in 2007, Sean finally signed to G.O.O.D. Music, joining a roster that was much more robust and less curated than it is today. Though acts like Common, Mr. Hudson, Mos Def, Cyhi the Prynce, John Legend, and Consequence have come and gone, Sean has remained.

Since then, the 28-year-old’s career has treated him to more ups and downs than the city of Detroit itself. And all of it has been recorded in the verses of song. Celebrations, deaths, failures, breakups and makeups comprise Sean’s output. So much so, his music tends to hint at, and perhaps sometimes even foreshadow, events in his real life. Finally Famous was a buoyant reflection on making it in the industry after years of hard work and uncertainty. Dark Sky Paradise surprisingly revealed a more acrimonious side of the rapper. Songs like “I Don’t Fuck With You” seemingly took aim at his former fiancee actress Naya Rivera. Similarly, “All Your Fault” references the mediocre performance of his sophomore album, Hall of Fame, the disappointment perhaps being compounded by his breakup with Rivera. “We done made it through hell and disaster / my crib done got bigger / my woman got badder,” gloats a Sean who has returned to confidence and to the dating scene — at the time he had started a new relationship with pop star Ariana Grande.

It’s only natural that I Decided. would bring listeners into another chapter of Sean’s life, one that is no less relatable than what he’s revealed in the past. The album does feel a bit like a final metamorphosis; the last leg of an odyssey where the hero has finally learned to work with the pull of fate rather than against it. Last year, Sean co-founded alt-R&B duo TWENTY88 with his current girlfriend, singer Jhene Aiko. The two worked together on prior projects dating back to Sean’s sophomore album, Hall of Fame. When TWENTY88 was formed, Aiko was still married to producer Dot Da Genius, but after their relationship soured, rumors began to circulate that she and Sean were dating. The resulting social media commotion — tweets and Instagram posts were fired off by both Dot and Aiko — led to accusations of infidelity on both sides. Eventually the drama reached Sean, who had a rather public falling out with former G.O.O.D. Music signee, Kid Cudi, after the Cleveland rapper took to social media to defend longtime friend and collaborator Dot.

One of the biggest things I’ve learned in life is forgiveness.

The personalized vitriol of Sean’s popular single, “I Don’t Fuck With You,” might lead one to expect some form of retaliation against Cudi; if not for pride reasons, at the very least for the publicity a diss track would undoubtedly garner. However, the markedly more Zen iteration of Sean that appears on I Decided. is at peace with the reality that some relationships are unsalvageable and some rumors just aren’t worth addressing. “One of the biggest things I’ve learned in life is forgiveness,” Sean explains. “Forgiving yourself, forgiving others and not holding on to grudges. It takes energy to hold a grudge, it’s almost like paying a fee for something you don’t really need every month. I also recently read that anything you consider a mistake or a failure is just an opportunity to turn things into something greater. No pun intended but it’s an opportunity to bounce back. That’s one of the themes of the album, even though it did take a while to realize that, and come to the point of looking at everything I’ve done in life, that I thought was a mistake, as a lesson that made me a better person. After I did that my life did adjust for the better though. I was no longer spending valued energy on things that didn’t matter.”

“No More Interviews,” a standalone single released in October 2016 seems to be Sean’s last cathartic swipe back at the naysayers, former friends and gossips. “This is my last time putting my ex in a song even though the last one went triple platinum,” raps Sean in reference to singer Ariana Grande whom he dated prior to his relationship with Aiko. He addresses his falling out with Kid Cudi much less dismissively, stating, “What happened to our family ways, though? / When I had put you on that song with Nas, you had told me you was forever grateful / And that we was brothers, so it hurt to hit the internet to find out that me and you don’t fuck with each other / Over a miscommunication that probably could be fixed with a five minute conversation.”

“I definitely learned about patience with this album,” Sean says, reflecting on what a life of constant public exposure and feeling underestimated has taught him. “Going through the things that inspired a lot of it, whether it was current, ideas from the past, or things I hadn’t really touched on all the way… I tried to incorporate all of those things. This is my first time making a project with a story, so it’s my first concept album. The story is kind of a narrative for me; it’s about how I feel and a lot of the things I’ve gone through. A lot of times I do feel like the older me is guiding me. I think that wisdom really helps me progress.”

Sean also found that the nomadic lifestyle of touring and back-to-back media appearances could actually have a positive effect on his creative process. “I recorded Dark Sky Paradise in one place but I recorded about 35 to 45 percent of the new album on the road. I think that gave it a different feel and made me approach the songs in a different way. I recorded most of it in Europe, specifically, so being overseas was a different experience for me than recording in America. It was great though. We were in a little eight-by-eight room — I’m talking super small to where only about two people could fit in there and you couldn’t even stand straight. We were in the back of the tour bus in this little section we turned into a studio. That’s where I recorded songs like ‘Move’ and worked on ‘Bounce Back,’ ‘Oh Me’ and ‘Inspire Me.’ A lot of the major songs on I Decided. were recorded on the road and I think it made a major difference.”

The album is also broken up into four acts. Combined, they tell a complete story of a wasted life, death, rebirth and second chances. “You get the first part of the album with ‘Light’ and ‘Bounce Back’ and ‘No Favors.’ ‘Light’ is when you realize that all you ever needed is inside you. Once you get it right on the inside that’s when everything on the outside starts changing and brightening up too. Then you have ‘Bounce Back’ and it’s like you’re picking yourself up from your losses, and then ‘No Favors’ is when you’re all the way charged up. The next act is more about relationships. It’s like you’re going after the person you think is your one true love and things end differently than what you thought. The third act is a little darker because it’s way more themed around depression, maybe there’s even suicide on your mind. Then when you get to the last act it’s like God and family pulling you out of the rut and helping you realize that what you’re going through is bigger than you.”

Sean’s polished explanation is so neatly packaged it’s press release worthy, nevertheless you can’t accuse him of being disingenuous. I Decided. isn’t trying to win listeners over with subtle metaphor or deep existential questions. The concept of the underdog somehow getting a second chance to finally be the person they’ve always dreamed of being is easily discernible because Sean’s music tends to be like an all-access, all-ages concert — there’s something for everyone. Even the album’s last four songs — “Sunday Morning Jetpack,” “Inspire Me,” “Sacrifices” and “Bigger Than Me” — seem laser-focused to this purpose. Not only do the titles read like chapters in a 90-day self-help book, they bring the story arc to the satisfying kind of happy ending we expect from our favorite feelgood movies.

Maybe there is no such thing as right or wrong, but maybe it’s just what you choose, you know? Whatever you do choose puts you on the trajectory towards your end point in life.

The story makes sense for an artist like Big Sean, whose platinum-selling projects have always found that happy place between popular music and niche hip-hop. I Decided. doesn’t depart from the approach that seems to work, Sean is simply more confident in himself and more centered than before. “Everything ties back to this idea of being certain about yourself and making a declaration about your life,” he explains. “That’s where I feel like I’m at now. I think that it’s something I had to work hard to find. It’s not easy to be secure with yourself, to be definitive and to know what you want. You have to go through a lot of life experiences… and hopefully mine inspire people. Life is about the choices you make so you have to make definitive choices at the very least. Maybe there is no such thing as right or wrong, but maybe it’s just what you choose, you know? Whatever you do choose puts you on the trajectory towards your end point in life, and that’s something I believe we can all apply to how we view the world.” Whatever end point Sean envisions, it seems likely that he will act as his own seventh trumpet, proclaiming his fate in universally relatable songs, long before that end actually arrives.

This story originally appeared in Highsnobiety Magazine Issue 14, which is available now from our online store, as well as at fine retailers worldwide.

Brands Featured: Aimé Leon Dore, Casbia, Dress Down Day, DSQUARED2, Opening Ceremony, Perry Ellis, RETROSUPERFUTURE, Rolex, Supreme

  • Photography: Thomas Welch
  • Styling: Jenny Haapala
  • Photography Assistant: Bryan Luna
  • Styling Assistant: Rashied Black
  • Special Thanks: Opening Ceremony & Gentry
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