Who are the coolest people you ever hung with?

Rob Van Dam. He's one of the coolest, most down to earth person I've ever met.
 
Tough to say. I've known some cool people over the years. People who are open-minded and intelligent, and just plain fun to be around.

But it seems like you're asking about celebrities and not necessarily about cool people. So in that case:

Tug McGraw and Reggie Theus are probably the most famous people I've had a conversation with. Though Nick Eddy was my high school track coach, and he was famous back in the day.
 
Tim Armstrong from Rancid is probably the coolest guy in the world. I met him at a concert and me and my ex hung out in a tent with him for a couple hours, drinking. It was awesome.
 
I was lucky enough to have a (relatively brief) conversation with David Lynch once, mainly about the post-production process and the evil, evil people that are corporate executives.
Also, I dunno if anyone knows the band Gama Bomb, they're still relatively obscure, but I hung out with them after a show from around the time they were recording their first album, drinking and talking about Siouxsie and the Banshees and old school video games.
 
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