Drake

He played a wheelchair-bound basketball star on Degrassi for seven seasons, reportedly using his acting income to help cover his mother's medical bills while quietly recording mixtapes in Toronto. His 2009 So Far Gone cracked the formula open: a kid singing about feelings in a genre that mostly treated feelings as a liability. Lil Wayne signed him. Thank Me Later debuted at No. 1, and every studio album since has done the same. He didn't just top charts. He made rap-singing the default setting, and half the genre has been trying to sound like him ever since.

The Kendrick Lamar beef of 2024 was the first major public loss of his career. "Not Like Us" hit No. 1, swept five Grammys including Song of the Year, and Lamar performed it six times in one night at a June concert in Inglewood. Drake answered with a federal defamation lawsuit against UMG, alleging stream manipulation and promotion of lyrics calling him a pedophile. The court dismissed it in October 2025. His UMG contract was reportedly up for renegotiation in 2025. Still the highest-ranked rapper on Spotify's 2024 Wrapped, which doesn't quite cover the sting.

He's Black and Jewish, grew up in Toronto between a working-class neighborhood and a Jewish day school, had a bar mitzvah, and spent seven years on a soap opera before rap took him seriously. The biography reads weirder the closer you look: his dad drummed for Jerry Lee Lewis, his maternal grandfather owned a furniture factory in Toronto, his son's mother is a French former adult film actress. Pusha T outed the hidden son in a 2018 diss track, and Drake absorbed it and kept selling out stadiums. The drama doesn't stick to him the way it should.