41. Drake – "Light Up" (Feat. Jay-Z)
Drake is like that guy at the bar who oscillates between talking about his emotional problems too much and trying to be slick at all the wrong times, so Jay has to swoop in with show-stealing aura. Equal parts braggadocio, confidence, and counsel, Jay zones on a verse that lacks any fucks to give while schooling Drake on what winners do. I'll let you expound on who you think he's taking shots at here, but that Windows 7 line gets me every time.