By now, you’ve seen more than enough Wheelchair Jimmy memes to be intimately aware of Aubrey Drake Graham’s five-year gig on the Canadian drama Degrassi: The Next Generation. His rap career was well on its way by the time he left the show in 2009. He released his first mixtape, the aptly titled Room for Improvement, in 2006, and “Replacement Girl,” a collaboration with early ally Trey Songz from 2007’s Comeback Season tape, became the first track from an independent Canadian rapper to be featured on BET. Houston talent scout and CEO of Rap-a-Lot Records, Jas Prince, discovered Drake’s music—again on MySpace (those were the days)—and convinced Lil Wayne to listen. When Wayne finally obliged, he requested Drake be flown out to Houston a few days later. (Prince has since filed a lawsuit against Drake’s management team claiming an agreement to split profits between himself and then-manager Cortez Bryant was never honored.) All the same, Drake flew to Houston in 2008 to meet Wayne for the first time in his tour bus.
“Wayne was getting like the most painful tattoo in the world,” he recounted to Interview Magazine in 2011. “He was getting these huge wings on each side of his body.”
Wayne played him Tha Carter III, which had yet to be released, and Drake stayed on the road with him for a week and a half, during which they recorded “Ransom” and a remix to “Brand New.” Drake’s star-making mixtape So Far Gone dropped in 2009, and a few months later, he announced that he was signed to Young Money.