Sit with Cruise, he's so small I would always win the armrest war. Plus Oprah is so fat she would spill over and she would probably talk too much.

Kick Gallagher in the melons, for sure. Ask Dinah Shore about casting couches in old hollywood and about Burt and Dom sleeping together.
Drinks with Andy Griffith. Just to ask him filthy questions about Mayberry and make him blush. (you know Floyd was a molester and Ernest T was fucking the chickens)