35. David Letterman
Letterman was awarded Kennedy Center honors last December, and for good reason. He's up in that jazz legend/famous author realm of great American artists at this point; you can go years without watching The Late Show then check back in to find him exactly the same dry genius you remember – only now there's a lovable cantankerous Midwestern grandpa side to go with it. And even at 65, Letterman can still bring the fourth wall-smashing fire; in a recent retrospective interview with Regis Philbin he followed up a clip of some of his Eighties standup from The Tonight Show by telling Regis, with embarrassed rage: "If you roll anymore tape I'm coming across the desk. There's gonna be bloodshed right here. I can take you."