Album: So Far Gone
Label: Young Money, Cash Money
Best Pick Up Line: "Sweat pants, hair tied, chillin' with no make-up on/That's when you're the prettiest, I hope that you don't take it wrong."
This single off So Far Gone helped Complex cover star Drizzy Drake smash the airwaves and assured he'd have no problem "smashin' em allllll" if he wanted. The video was a bit of a stretch (GET IT?), and had him in the doghouse with some female fans, but he's managed to work his way back into their good graces.