Ash. That guy would be hysterical. Being his drinking buddy would pretty much make my life.
Seth Gecko would be prettty damn entertaining. Not gonna say I wouldn't end up dead at the end of the night, but it'd be fun.
Peter Vincent mainly because I'd want to hang with that guy whenever. He's just one cool cat.
Then of course Freddy Krueger. He'd have some sick sense of humor and would just be an overall good time.