Even if he grew up surrounded by music (his Dad was a bluesman while his brother played with Levon Helm plus the Chairmen of the Board), the boisterous rapper known as OB O'Brien broke through thanks to his sense of humor and recurring comedic roles in his boss Drake's videos. Like Drake,O'Brien was born and raised in Hamilton, Ontario. He wrote rhymes, produced beats, and joined drama clubs during high school, but he met Drake thanks to video gaming, just as the future rap superstar was finishing his run on the television series Degrassi: The Next Generation. The two worked on a post-Degrassi series that never got off the ground, but as Drake became the man behind hits like "Started at the Bottom" and "HYFR," O'Brien became the "bearded dude" in the accompanying videos. He also began writing for Drake and Boi-1da, then in 2014, he released the track "Hazelton Trump" onDrake's label OVO.