Conan O'Brien

More than any television comic since the great Ernie Kovacs, Conan O'Brien is at heart a surrealist. His funniest inventions—The Masturbating Bear, If They Mated, The Walker, Texas Ranger Lever, etc.—suggest the mind of a 12-year-old Dadaist, tossing off both strikingly absurd juxtapositions and genially rude jokes. A former staff writer for Saturday Night Live and The Simpsons, O'Brien had almost no on-camera experience when producer Lorne Michaels chose him to take over David Letterman's timeslot in 1993. Unfortunately, it showed—for its first year or two, Late Night with Conan O'Brien was painfully bad. But as O'Brien gained confidence in his own peculiar comic sense, he became the most consistently funny and engaging host in late night TV. What he is not, however, is a Johnny Carson-style comforting presence—O'Brien's self-deprecating comic persona is that of a man twitchily uncomfortable in his own skin. This works better at 12:35 than immediately after the local news, so O'Brien's too-soon-interrupted stint as host of The Tonight Show would likely have been doomed to fail even if NBC's executives hadn't panicked and lunged back to the insipid Jay Leno. Talents like O'Brien's work better on the margins.