Barkley's gotta be the number one athlete of all time I'd hang out with. Mickey Mantle fucking partied but probably was kind of an uninteresting hick. Babe Ruth was a slob and looks like he smelled. Some dudes might say AI, but I guarantee you you would get bored hanging out with Iverson real quick and you'd be lucky if you didn't get robbed or beat up. Um. DiMaggio, Favre, and Brady are/were tools. Jeter would outshine you. Gronk seems like a good time but I don't know much about him. Honestly of active athletes I might hang out with Jared Allen. Dude seems legit funny. Anybody who signs copies of his DWIs for fans is probably pretty down to earth and chill to crack a Coors Light with.
But all time definitely Barkley. If only for what he said to the cops.