William S. Burroughs and Hunter S. Thompson--strong drink and firearms, yer bugger.
Go on the road with Kerouac or Kesey.
Share a bottle of champagne with Capote at Studio 54.
Kick Hemingway's butt at arm wrestling, kick Scott Fitzgerald's butt (period) and take Zelda out on the town.
An all-nite pub crawl with Bukowski.
But first and foremost, I'd love to have been a regular at Villa Diodati during that gloomy, stormy summer of 1816. Blam, you got the Shelley's, Byron, Polidori...I've read even Monk Lewis stopped by once. The birthplace of English Horror right there in a moody, delicious setting. (And maybe years later sweep the widowed Mary off her lonely feet, take her back to the states with me. Hey, why not? It seems she had a thing for Washington Irving, so...)
I could do this all day, dammit...