Owen Wilson. Plain and simple. The man cracks me up and I think he'd hilarious in every role he has. I've been a fan for about 15 years now and he never ceases to crack me up.
Second would be Jase Robertson from Duck Dynasty. Another person that always cracks me up and just seems like he'd be so much fun to hang out with and get in trouble with.
What about you? Who do you wish you could hang out with/ were friends with ?