His fourth and fifth albums, I Decided (2017) and Detroit 2 (2020), both also debuted atop the chart; the former was supported by the single "Bounce Back", which peaked at number six on the Billboard Hot 100 and remains his highest-charting song.

[3][5] Anderson's grandmother, Mildred Leonard, served in World War II, and was one of the first ever black female captains in the United States Army.

[7] 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.

His hit single, "Get'cha Some", produced by WrighTrax, attained media attention and led to articles in The Source and the Detroit Metro Times.

[13] 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.

[18] 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, Pop Wansel, Xaphoon Jones and The Neptunes.

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".

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.

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.

[38] He would lead with Video singles for songs entitled "IDFWU", "Blessings", "I Know", "One Man Can Change The World", and "Play No Games."

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.

On July 24, 2019, Big Sean released his first solo single since 2017, "Overtime", produced by Hit-Boy, Key Wane, and the Tucker Brothers.

[50] On July 26, he released the song "Single Again", which includes background vocals from Jhené Aiko and Ty Dolla Sign.

[51] On August 26, he released the single "Bezerk" featuring ASAP Ferg, performing it at the 2019 MTV Video Music Awards.

[53] On August 25, he released the album's lead single, "Deep Reverence", featuring late rapper Nipsey Hussle.

In 2020, Big Sean starred in the Showtime series Twenties in the recurring role of Trsitan, an anti-social media character who learns the value of online connection.

[59] In October 2021, Big Sean released a collaborative extended play (EP) with record producer Hit-Boy titled What You Expect, which peaked at number 76 on the Billboard 200.

[60] In February 2022, Big Sean released a duet single with American singer Queen Naija titled "Hate Our Love", which entered the Billboard Hot 100 at number 88.

In July 2024, Big Sean released the collaborative single "Tobey" with fellow Detroit rappers Eminem and BabyTron; it peaked at number 27 on the Billboard Hot 100 and served as the second single for Eminem's twelfth album, The Death of Slim Shady (Coup de Grâce).

Two weeks later, he performed a freestyle on the radio show On the Radar, wherein he indirectly affronted his former label boss Kanye West.

Seemingly undeterred, he wrote on the platform himself later that month: “The pressure of life (being a new Dad, being [an] artist that’s growing, being a human in development, etc) and embracing it all led me to a lot of clarity on what I needed to focus on to find a piece of happiness [...] The past few years making this album have been a journey to say the least, but l’m just glad we finally here.” before he announcing his sixth album, Better Me Than You to be released on August 9.

[75] He credits therapy, a healthy lifestyle, exercise and taking a break from touring to refocus on his music as instrumental in his recovery.

During the same year, the foundation donated a recording studio for students at Big Sean's alma mater, Cass Technical High School.

[78] In December 2018, Big Sean in partnership with Ally Financial, Thurgood Marshall College Fund & the Sean Anderson Foundation, created an annual scholarship competition for HBCU students called “Moguls in the Making.”[79] In 2019, the foundation partnered with Boys & Girls Club of Southeastern Michigan, donating a second $100,000 recording studio to the club during that year's D.O.N.

[77][80] Since 2012, the foundation has participated in the annual All Star Giveback on Thanksgiving, where it distributes turkeys, trimming and canned goods to Detroit residents.

[85] He has an endorsement deal with Adidas, through which he has released his own "Detroit Player" line of sneakers,[86] and is a follower of the Rosewood clothing style.

[93] In that role, he leads the design of team apparel, with practice jerseys bearing his “Don Life” logo, and other non-game, community-driven initiatives.

[96] On October 26, he pleaded guilty to second-degree unlawful imprisonment, and was fined $750;[97] the charges of third-degree sexual abuse were dropped as part of the plea bargain.