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In his later years in high school, Sean gained a valuable relationship with Detroit hip-hop station WHTD; he would show his rhyming skills on a weekly basis as part of a rap battle contest held by the station.In 2005, Kanye West was doing a radio interview at 102.7 FM.
After releasing a number of mixtapes, Sean released his debut studio album, Finally Famous, in 2011.
According to Big Sean, West enjoyed his freestyle: "As we get to the entrance of the radio station ... His hit single, "Get'cha Some", produced by Wrigh Trax, 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.
He released his second studio album, Hall of Fame, in 2013.
Sean's third studio album, Dark Sky Paradise, was released in 2015 and earned him his first number one album in the US.
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. Finally Famous, Sean's debut studio album, was released June 28, 2011, and spawned three hit singles; "My Last", "Marvin & Chardonnay" and "Dance (Ass)". R." and "Flowers" were leaked in July 2011, speculation began of a new mixtape.
In an interview on Conspiracy Worldwide Radio, Sean discussed the role Kanye West and No I. 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 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. 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".
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. An unauthorized leak of his collaboration with Drake, called "Made" made its way onto the internet on April 30, 2010.
In 2017, he released his fourth studio album, I Decided, which debuted at number one on the US Billboard 200 chart.
Big Sean is often heard saying "west side" in his songs; he is referring to the west side of his hometown Detroit, Michigan.
Hearing about this, Sean headed over to the station to meet West and perform some freestyle.