Would the "celebrity" have a security detail?

Living: Keanu Reeves

Dead: Marcus Aurelius

Fictional: Jean-Luc Picard

Oh you know I'd force a certain King in Chief to sit down with me for four hours, it would be delightful, with a spectacular closing act.

Living: David Attenborough

Dead: Marilyn Monroe

Fictional: Ford Prefect

It would be interesting to talk to Decartes, but I don't speak Français, so it would have to be... idk... Nick Bostrom would be interesting

Keanu Reeves seems like such a nice guy! I haven't heard a single bad thing about him!

Uncle Roger. I want to either enjoy the roast of YouTube videos or have yummy food that I wouldn't necessarily order myself

"Never meet your heros." is as old as celebrity itself.

I think many of my heroes live larger in my mind than they could or should ever fulfill; they couldn't possibly live up to that hype and I wouldn't want to take it from them through the actuality.

Damn shame.

(Side-glance at you UK BBC.)

George Washington Carter, my personal hero

Do I have to do it tonight, or can there be a 'waiting period'? (I have nothing to wear...)

I'm not burning to have a conversation with any celebrity in person, but I'd probably pick some famous philosopher or scientist or something so that the conversation would at least be interesting.

Henry Cavill, seems like a nice guy, and I think we would have a lot of common interests to talk about.

Hmm.

Honestly John Rys Davies, based solely on Dominic Monaghan's description of him ordering dinner when filming Lord of the Rings.

"John Rhys-Davies… took us to a restaurant. And it was when we’d only just started to get to know John. And we sat down at this huge, long table, and he said, “I think I will order the food for tonight.” And we said, “Oh, ok, on you go John.” And you know, we were having a conversation, and the waitress came over, and John ordered food that would probably have fed 35, maybe 40 people. And there were about 12 of us. And he just said, “We’ll have nine lobster and 15 shrimp, and 12 red snapper, 15 filet mignons, and some grilled mushrooms. I’ll have 12 onions and a wild boar…” You know? All this kind of stuff - just like, “Pheasants, and grouse, and - do you have partridge? Bring the partridge.”

Neko Case!

Brennan Lee Mulligan, would love to just geek out about ttrpg theory with him for 6 hours.

Joe Mama

Living: Gabe Newell

Dead: Sir Terry Pratchett

Fictional: Commander Samuel Vimes

Jam Hsiao because I really like his energy and his music. Only major hurdle would be the language barrier between, if we don't include the nervous energy I'd most likely radiate.

That one guy's dead wife obviously.

Stephen Hawking was the only person I'd have used this offer for, now I really can't think of anyone. Brian Cox maybe?

Wallace Shawn

Mmmm nobody, because I don't respect or care for anyone who is considered to be a celebrity. I just don't get it.

I would choose the 500k

David Gilmour (hopefully with a quick jam session as dessert)

Probably Andre Gregory.

Living: Bobby Fingers

Dead: Nietzsche

Fictional: Ignatius J. Reilly