Detroit rapper Big Sean began writing poetry as a kid and was selling his own CDs by high school. His break came in 2005 when he freestyled for Kanye West in a radio station parking lot—an encounter that led to a deal with West’s GOOD Music label. After a trio of mixtapes, Sean debuted in 2011 with Finally Famous, an album that balanced wit (“My Last”), introspection, and swagger (“Dance [A$$]”). He quickly became one of the most versatile rappers of the 2010s, and has continued to deliver bangers (“Blessings”) and heartbreak ballads (“Beware”) ever since. He’s also the consummate collaborator, not just on his own albums (“Deep Reverence [feat. Nipsey Hussle]” and “Body Language [feat. Ty Dolla $ign and Jhené Aiko]” from the guest-packed Detroit 2) but also on joint full-length projects with Jhené Aiko (2016’s TWENTY88) and Metro Boomin (2017’s Double Or Nothing).