Hmm, Caligula or Debbie Gibson…
Are you sure I can’t get together with the both of them? I’d sure love to hear that dinner conversation. 
Russell Crowe & Jackie Chan.
Look, I already know I’m obnoxious. My best guess is that Russell Crowe would put up with me for maybe… Maybe… 15 minutes. Then he’d take a poke at me.
And Jackie Chan would smile & laugh his ass off.
Günther Lütjens. Another navy man (even if he was a skimmer) - he’s got to have some great sea stories!
Salvador Dali, for sure.
Hmm. Scott Bakula or Zachary Ty Bryan… Hmmmm… Hmmmm… I do like Quantum Leap…
John Lennon it is!
Alyssa Milano, best known as Phoebe Halliwell on Charmed.
Malcolm X
I would ask him to select the restaurant and topic of conversation. (Which would probably start with “How did I get HERE?”) I’ll pick up the tab.