3. Shooter McGavin (Chris Macdonald) in Happy Gilmore
I don't know why, but there's something about 'ol Shooter that stays with me. I realize he's smarmy and self-absorbed, but he looks like he could knock back a few with you and subtly manipulate the hell out of other bar patrons. He's one of those guys who you would be friends with and everyone would wonder why. I just understand Shooter and his frustrations of everyone not knowing how awesome he really is. He tries to be evil, but is terrible at it. That's what makes him so endearing to me. Because of that I personally was rooting for him to win that last tournament. Sometimes you just need to hang with a scoundrel to make yourself feel better. Just remember to stay out of his way and listen to what he says, and don't eat what he eats for breakfast.
2. Jabba the Hut (Larry Ward) in Return of the Jedi
This might be my number one. First of all, he has an awesome fortress set up in the middle of the desert. Second, hanging out with him would be just one giant party. It appears everyone at the palace can just cavort around casually, pass out anywhere they want, then wake up and go for a cruise on the old sailing barge. I'd take in the views, dance away to that wicked band, drink his good scotch, and ogle his princess laying there in a gold bikini. I'd even take his pet whatever-the-heck-that-is outside on occasion to go to the bathroom.