Big Sean

In his later years in high school, Sean showed his rhyming skills on a weekly basis as part of a rap battle contest held by Detroit hip-hop station WHTD.[7] In 2005, Kanye West was doing a radio interview at 102.7 FM. Hearing about this, Sean headed over to the station to meet West and perform some freestyle. Initially West was reluctant to hear him, however, he gave Sean 16 bars to rap for him. According to Big Sean, West enjoyed his freestyle: "As we get to the entrance of the radio station ... we stopped in the middle of the doorway. He starts looking at me and bobbing his head."[8] After the freestyle, Sean left West his demo tape. Two years later, West signed Big Sean to GOOD Music. Sean has cited West, Eminem, The Notorious B.I.G., and J Dilla as his influences.[9][10]

Sean in 2009.

On September 30, 2007, Big Sean released his first official mixtape Finally Famous: The Mixtape. His hit single, "Get'cha Some", produced by WrighTrax, attained media attention and led to articles in The Source and the Detroit Metro Times. He also recorded a music video for "Get'cha Some", which was directed by Hype Williams.[11] Sean released a second mixtape hosted by Mick Boogie on April 16, 2009, called UKNOWBIGSEAN. It featured the songs "Million Dollars", "Get'cha Some" and "Supa Dupa". This mixtape includes 30 tracks.[12] Sean released a third mixtape hosted by Don Cannon on August 31, 2010 called Finally Famous Vol. 3: BIG, which features include major artists like Bun B, Chip tha Ripper, Curren$y, Tyga, Drake, Mike Posner, Chuck Inglish, Asher Roth, Dom Kennedy and Chiddy Bang. The mixtape includes 20 tracks.[13]

An unauthorized leak of his collaboration with Drake, called "Made" made its way onto the internet on April 30, 2010. In an interview with TheHipHopUpdate.com on May 1, Big Sean expressed his disappointment over the leak, calling it an unfinished version both musically and lyrically. Big Sean's official Facebook page confirmed that his debut album Finally Famous & Consequence's Cons TV would be released on September 14, 2010. On August 31, Big Sean tweeted that the album was not coming out on that day, but it would be coming out sometime in 2011.[14]

In an interview on Conspiracy Worldwide Radio, Sean discussed the role Kanye West and No I.D. have had in the development of his first studio album's sonic direction as well as the challenges of being inside the studio with West. The album's lead single, "My Last", features vocals from Chris Brown and was produced by No I.D.[15] According to Amazon.com, Big Sean's Finally Famous was delayed by a week, with a tentative release date set for June 28. Big Sean revealed the cover art for his G.O.O.D. Music debut and explained that the one-week pushback was to be blamed on sample and feature clearance issues.[16] The official tracklist was revealed on June 7.[17]

Sean in 2011.

Finally Famous, Sean's debut studio album, was released June 28, 2011, and spawned three hit singles; "My Last", "Marvin & Chardonnay" and "Dance (Ass)". The album featured guest appearances from Lupe Fiasco, John Legend, Pharrell, Kanye West, Roscoe Dash, Wiz Khalifa, Chiddy Bang, Rick Ross, Nicki Minaj, Pusha T, and included production from No I.D., The Legendary Traxster, Andrew "Pop" Wansel, Xaphoon Jones and The Neptunes.[18][19][20][21] When the songs "O.T.T.R." and "Flowers" were leaked in July 2011, speculation began of a new mixtape. Sean confirmed in an interview June 28, 2011 that a collaborative mixtape between him and "two other guys in hip-hop that are just killing it right now" will be released "in a couple of weeks". Wiz Khalifa and Curren$y, were the suspected featured rappers on the mixtape.[22] However, Wiz Khalifa later confirmed that there would be no mixtape, claiming that the songs were created, "just for fun".

In September 2011, Big Sean confirmed in an interview with the Daily Tribune that he'll be working on his second album during the I Am Finally Famous Tour and plans to release the album sometime in 2012.[23] On October 19, 2011, Kanye West announced on his Twitter plans for a Spring 2012 GOOD Music album release.[24] On April 6, 2012, "Mercy", the lead single from the GOOD Music compilation album, Cruel Summer, was released.[25] The song, produced by newly signed in-house producer Lifted, features Big Sean along with Kanye West, Pusha T and southern rapper 2 Chainz.[26] Big Sean then announced his fourth mixtape would be titled "Detroit" and would serve as a lead-in to his second studio album.[24] He then began promoting the mixtape, releasing short versions of the songs on his YouTube page. On September 5, 2012, Big Sean released the mixtape Detroit which features guest appearances from fellow rappers J. Cole, Juicy J, King Chip, French Montana, Royce da 5'9", Kendrick Lamar and Tyga.

Big Sean pushed back the release date of his second studio album Hall of Fame, and was eventually released on August 27, 2013. The album has skits to give it a "classic feel", and includes features from multiple artists, including Lil Wayne, Miguel, and Nas. The album's production was primarily handled by No I.D., and Key Wane along with additional production from Hit-Boy, and Da Internz, Mike Dean, Travis Scott, Xaphoon Jones and Young Chop among others. Big Sean also stated in an interview that he was in the studio with fellow Detroit native Eminem. Sean went on to say they made a "Detroit classic" but he is unsure if it will be on Hall of Fame because of "timing issues".[27] Hall of Fame had spawned five singles, "Guap", "Switch Up" featuring Common, "Beware" featuring Jhené Aiko and Lil Wayne, "Fire", and "Ashley" featuring Miguel.

A month prior to the release of Hall of Fame, Big Sean told Complex that he had already begun work on his third album due to the inspiration from his new relationship.[28] On September 12, 2014 Big Sean announced that he had signed a management deal with Roc Nation.[29] Later that same day he released four new songs titled, "I Don't Fuck with You", "Paradise", "4th Quarter" and "Jit/Juke". Producers for these songs include, Mike Will Made It, DJ Mustard, Kanye West, DJ Dahi, Nate Fox, Da Internz, L&F, and Key Wane.[30][31] "I Don't Fuck with You" was released to iTunes on September 19, 2014.[32] In an interview with Sway Calloway, Sean confirmed that Lil Wayne will be featured on the album.[33]

Sean performing in April 2015.

On January 25, 2015 various artists who worked on Big Sean's upcoming third studio album such as Kanye West, Ty Dolla Sign, DJ Mustard, Drake, Travis Scott and Ariana Grande posted the album cover to Twitter or Instagram.[34] The next day, Big Sean posted a trailer to his new album which revealed the album's release date as February 24, 2015.[35] The album, Dark Sky Paradise debuted atop the Billboard 200 making it his first No. 1 album.[36] He would lead with Video singles for songs entitled "IDFWU", "Blessings", "I Know", "One Man Can Change The World", and "Play No Games." As of February 1, 2016, Dark Sky Paradise was certified platinum. On December 31, 2015, Big Sean released a track recapping 2015, "What A Year (Ft. Pharrell Williams & Detail)".

On March 25, 2016, Big Sean released a track to celebrate his 28th birthday, "Get My Shit Together". Two days later he announced a self-titled album with Jhené Aiko, as Twenty88, scheduled to be released on April 1, 2016, exclusively on Tidal.[37] The album was released on April 5, 2016 on Apple Music and Spotify. A week after the exclusive release of Twenty88 on Tidal, Big Sean and Aiko released a 15-minute short film called Out of Love, which is composed of several recordings from the album. Around the same month, upon the wake of the Flint water crisis, Big Sean tweeted to the city's official Twitter account, asking if he could do anything to help, and later on donated $10,000.[38]

On October 31, 2016, Big Sean released "Bounce Back" as the lead single from his fourth studio album, I Decided, which was released February 3, 2017.[39] "Moves" was released as an instant-grat on December 16, 2016. Sean consulted the advice of Jay Z and Rick Rubin while working on the album.[40] Big Sean achieved his second number one album on the Billboard 200 chart, as I Decided debuted at the top. It earned 151,000 equivalent album units in the week of February 9, according to Nielsen Music. 65,000 of the amount were in pure album sales.[41] As of April 18, 2017, I Decided was certified gold.[42]

Two months after the release of I Decided, Big Sean was offered the official Key to the City of Detroit for his contribution to his own Sean Anderson foundation.[43][44][45]

On November 3, 2017, Sean and Metro Boomin released the single "Pull Up N Wreck", featuring 21 Savage. A month later, it was announced that Sean and Metro were to release a collaborative album titled Double or Nothing. The album was released on December 8, 2017, which included features from Travis Scott, 2 Chainz, 21 Savage, Kash Doll, Young Thug, and Swae Lee, and included the single "Pull Up N Wreck".[46]

On July 24, 2019, Big Sean released his first solo single since 2017 titled "Overtime", produced by Hit-Boy, Key Wane, and the Tucker Brothers.[47] In an interview with Beats 1 Radio, Sean said he was "returning to his roots" with the single ahead of his forthcoming album.[48] On July 26, he released the song "Single Again", which includes background vocals from Jhené Aiko and Ty Dolla Sign.[49] On August 26, he released the single "Bezerk" featuring ASAP Ferg, performing it at the 2019 MTV Video Music Awards.[50]

On March 25 (Big Sean's 32nd birthday), he announced that his new record would be titled Detroit 2.[51] On August 25, he released the album's lead single, "Deep Reverence", featuring late rapper Nipsey Hussle.[52]

Detroit 2 was released on September 4, 2020, and features collaborations with Eminem, Jhené Aiko, and Lil Wayne.[53] The album debuted at number one on the Billboard 200, marking his third number-one album.[54]

On September 17, 2020, Big Sean revealed in a Reddit AMA that another Twenty88 album is "in the works". A track attributed to the project appeared on Detroit 2.[55] He has also announced that he plans of launching his own record label.[55]