Anything in a Business Suit.
Groucho Marx, Charlie Chaplin and Conan O'Brien over dinner at a sea-food restaurant.
Michael Williams, The Beatles, Bonzo Doo Dah Band, Tom Lehrer, Gilbert and Sullivan, Neil Innes, Drew Tretick, Andrea BocelliI like musicals and soundtracks: Andrew Lloyd Webber, Kurt Weill, Kander and Ebb, Danny Elfman, Mark Hollman, Stephen Sondheim, Carter Burwell, Jon Brion
Film people, rather. Charlie Chaplin, Buster Keaton, Marx Bros, Harold Lloyd, Laurel & Hardy, W.C. Fields, Woody Allen, Wes Anderson, Charlie Kaufman, Stanley Kubrick, Alfred Hitchcock.Lolita (1996), Rushmore, Royal Tenenbaums, Red-Headed Woman, Vertigo, Modern Times, Amelie, Patch of Blue, Monty Python (Grail and Brian), Eternal Sunshine of the Spotless Mind, Being John Malkovich, Secretary, (unfortunately anything with an age difference between the romantic leads, sado-masochistic undertones is always a plus).
Late Night with Conan O'Brien, Late Show with David Letterman, Strangers With Candy, Kids in the Hall, The Office (British), Ally McBeal, Boston Legal.
Authors instead: J.D. Salinger, Oscar Wilde, W.S. Gilbert, David Sedaris, Augusten Burroughs, Sir Arthur Conan Doyle, Kurt Vonnegut.
My mom, Conan O'Brien