Big Sean's Top 10 Defining Career Moments: From Kanye West Co-Sign to 'I Decided'

Big Sean, 2017
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Big Sean seen in the streets of Manhattan outside Phillip Lim during New York Fashion Week on Sept. 11, 2017 in New York City. 

"I know what it feels like to be the underdog, to know you're full potential and it not be recognized. All I can say is keep going, earn it," Big Sean wrote on Twitter the day his fourth studio album, I Decided, was released.

But Sean raps on the album's lead single "Bounce Back," he's always considered himself a "top 5" rapper even if others haven't caught on yet. And if his extensive repertoire of hits prove anything, it's his ability to hold his own against the most respect lyricists in the game.

The Detroit MC's career has been fueled by a series of well-thought-out -- and sometimes rather risky -- decisions that have aided in his success and rightfully placed the rapper in "best MC" talks. With a penchant for introspective rhymes and witty, braggadocios punchlines, the self-proclaimed “underdog” has gained acclaim for his top-charting songs and albums, high-profile collaborations, fashion deals and more.

And to think it all started with an impromptu audition for Kanye West in a hallway over a decade ago.

In honor of his 30th birthday today (March 25), Billboard takes a look at Big Sean’s career-defining moments. 

Auditioning for Kanye West -- 2005

Big Sean was making a name for himself in Detroit through a local station’s weekly Friday freestyle battles before an encounter with West eventually helped launch his career. When a friend of Sean told him West would be at a local radio station, the then-budding rapper seized the opportunity and showed up at the radio station, where he performed an impromptu freestyle for West. West was reluctant to hear the young spitter at first but then offered Sean enough time to spit 16 bars, even though he ended up freestyling for 10 minutes.

Signs with Kanye West’s G.O.O.D Music label -- 2007

Big Sean didn't hear much from West after his freestyle, but still had a career in music in his sights. He graduated Cass Technical High School with a 3.7 grade point average and gave up a full-ride scholarship to Michigan State University to pursue his rap dreams. The result? A placement on West’s G.O.O.D Music label in 2007. Sean even hit the road with West while he was crafting his 2007 album, Graduation.

Drops debut album Finally Famous -- 2011

After signing with G.O.O.D Music in 2007, the Detroit native doled out his debut mixtape under West’s label, Finally Famous Vol 1: The Mixtape, in 2007. But it wasn’t until 2011 that his proper debut was released. Sean led with “My Last” featuring Chris Brown as his first single, which was originally created for J. Cole.

“That record was actually made for J. Cole during one of his sessions,” No I.D, who produced the record, told Complex. “I told Cole it was going to be a single and he said, ‘Nah, I don’t know about that one.’ So I passed it for Sean while he was working on his album, and told him this would be the one, and he said ‘I don’t know about that.’ He thought it sounded too commercial or whatever.”

But being “commercial” is exactly what helped Big Sean gain further recognition. The song peaked at No. 30 on the Hot 100, and was followed up with “Marvin & Chardonnay” and the colossal hit “Dance (A$$) featuring Nicki Minaj.

Kanye West, Big Sean and JAY-Z release “Clique” -- 2012

2011 was a big year, not only for Sean but also JAY-Z and Kanye West, who dropped their collaborative album, Watch The Throne, the same year. Then, “Clique” happened. Big Sean joined Hov and Yeezy on the track, which was featured on G.O.O.D Music’s compilation album Cruel Summers. Flexing his lyrical dexterity alongside his mentors, Sean dished out witty lines (“I tell a bad bitch do whatever I say/ My block behind me, like I'm coming out the driveway/ It's grind day, from Friday to next Friday”) before making way for Hov and 'Ye.

Pop crossover success with Justin Bieber -- 2012

A year after releasing his debut album, the “My Last” rapper had proved to be a formidable force within hip-hop and his next order of business was making his presence known in the pop world. Who better to help him crack the pop charts than pop prince Justin Bieber? The Biebs and Sean joined forces for “As Long As You Love” at a time when the singer was making his transition from teen bops to more mature material for his third studio album, Believe. Sean’s collaboration with the teen sensation soared to No. 6 on the Hot 100 and earned the rapper his highest charting single to date.

Big Sean Unleashes “Control”

In 2013, Big Sean unleashed the fiery track “Control,” featuring Kendrick Lamar and Jay Electronica, and was instantly met with a wave of praise (and controversy), thanks to Lamar’s scathing verse where he warned his fellow rappers that he’s “tryna make sure your core fans never heard of you n----s.”

“I knew what it was for the culture of hip-hop,” Big Sean told Vibe. “You see how excited people are, and I wanted to do that for music -- make that play happen. It gave me like the feeling of how hip-hop was. How it used to be.” Sean said he had no plans of changing his part when Lamar sent his verse in and felt like the track could bring hip-hop back to the days of competition. Many people believe "Control" was the start of an ongoing feud between the rappers.

The Don Drops Dark Sky Paradise -- 2015

Big Sean’s third studio album found him in a more introspective state, especially on songs like “Win Some, Lose Some” and “One Man Can Change the World” -- an ode to his grandmother who passed away.

“Home-cooked meals after school all the time, birthday cakes, your favorite ones, every year. She was just great. She was the person who showed me that one man -- meaning human -- can change the world,” he said to Vanity Fair. “I always said that she deserved to have John Legend sing about her after a verse that I rapped about her. I’m happy that it turned out, and that I got to get her voice on the song. She’s a special person. She’s seen Hitler and Obama in the same lifetime, and I just hope that one day I can make as big of an impact as she did.”

But there are moments on the album that saw a playful Big Sean shut down a particular person on the anthemic “IDFWU,” featuring E-40, and boast about his lifestyle on the Drake-assisted “Blessings.” Dark Sky Paradise became Sean’s first No. 1 album on the Billboard 200.

Creating the experimental group with Jhene Aiko – 2016

Following the success of Sean and Jhene Aiko’s Dark Sky Paradise collab “I Know,” the pair realized their musical chemistry was way too strong for just one song, and fans were pining for more music from the two. Sean and Aiko made wishes come true when they formed TWENTY88 in 2016, which was a nod to their birth year 1988 and turning 28 just days before releasing the full TWENTY88 album.

The duo teased their joint project with a series of glossy, futuristic videos on their social accounts before unveiling the project on April Fool’s Day. TWENTY88 was replete with lust-drenched jams as well as songs about dealing with a toxic relationship.

Notches highest-charting single with “Bounce Back” -- 2017

At the end of 2016, Big Sean was frustrated with the media prying into his life, whether it was about his former relationships or feuds with other rappers. In response to the negative press, he unleashed “No More Interviews,” which served as a precursor to his next single, “Bounce Back.”

“Bounce Back” was the lead single off Sean’s latest album, I Decided, and became his first solo Hot 100 top 10 hit. On “Bounce Back,” Sean took aim at his detractors, rapping, “N---a how dare you stand before me and not respect my authority/ If you f--k with my glory, I'ma drop the L and get gory,” and reminded critics that he’s “been top 5.”

Big Sean Strikes Puma Deal -- 2018

Tour merchandise aside, Big Sean made his foray into fashion by joining the PUMA team in 2017. For his debut collection with the brand, Sean and PUMA recreated the classic suede sneaker to celebrate PUMA’s 50th anniversary. The collection also features classic athleticwear including hoodies, T-shirts, and joggers, doused in neutral colors. The full range will be available for purchase on March 31 on PUMA’s official site.