46. Lil Wayne "I'm Single" (2009)
Producer: 40, Omen
Album: No Ceilings/I Am Not a Human Being
Label: Young Money, Cash Money
"I'm Single" is essentially Wayne making a Drake record. He calls on 40 for the droning synth beat and works in the same honest misogynist space that Drake occupies. But Wayne forces sympathy with such an awkward charm that you almost feel bad for the guy while he's so maliciously cheating on his girlfriend. Even at his most dramatic Drake has never been so convincing. It's proof that while the student may have become the teacher for the moment, the teacher is still the master.