It has to be a living celebrity and they won’t do anything overtly illegal or sexual, they aren’t going to blow you or be the wheel man of your getaway car. They also won’t give you money or any gifts so the only thing you are taking away from this day is the story.
A caller to our local morning show said they’d pick Kevin Costner, have him squeeze into his Robin Hood: Prince of Thieves outfit and go to Target stores and shoot at the signs.
I would pick Matthew McConaughey give him a microphone and have him just narrate what I do all day like I’m in a Lexus commercial.
I would hire Paul McCartney or Elton John, and have them sit down with a guitar, or piano, and write a song from scratch, and then play a few of their favorite songs for an audience of one.
Neil deGrasse Tyson - just to hang out and talk about stuff. Maybe bring my granddaughter along because she’s a little STEM whiz and I’d like to see their interaction.
Seth Rogen. I’d order us some pizza, we’d get really stoned and watch This is the End and I’d get to hear his stories about it. (Tons of famous people in it; there have to be some good stories.) The idea being I’d get an in-person, unfiltered DVD commentary experience.
Hmmm. Well, poster neiltyson has been claimed, so I think I’ll go with David Chang of Momofuku fame. I figure I can get him to cook for me, and bombard him with questions on techniques as well as Asian-fusion options and have a great time, a great meal, AND learn something!
Arnold Schwarzenneger, to do a kickass morning workout with, and then have him narrate my day like @Sitnam thought of.
We could go grocery shopping: "Get to da shoppah!’
We could go to my doctor: "It is not a toomuh!"
Answer some work emails: “I’m afraid that my condition has left me cold to your pleas of mercy.”
Tell people what I do for a living: " . . . crush my enemies, see them driven before me, and hear the lamentations of their women."
I’m not seeing a downside to this.
Tripler
Close a SDMB post: “Hasta la vista, baby.”
If I can change the hypothetical a little: If I had to spend several hours in a room with celebrity…
Michael Palin
Jeff Bridges
Barack Obama (good pick I’ve borrowed from above; also because I have a relative who once hosted a dinner for him and Michelle when they were POTUS and FLOTUS)
I would gladly talk about anything they felt like. No photos, no autographs.
Good call-- it wouldn’t be much fun hanging out with a mouldering corpse
“Is Danny McBride 1/10 of the a-hole every single character he plays seems to be?”
And, of course, every single time he gets up to use the bathroom or get a drink from the fridge, get him to say “ah’ll be bahhhk!”
I considered a variety of musicians for my pick to jam with, but I already have a musician friend who is so much better than me that I can’t keep up. Keith Richards is a good pick-- like you say, not to jam with but just to hang out with and shoot the shit. It’d be fun to hear some catty stories about Mick Jagger, which I’m sure would come out after a little bit of Jack.
I’d say Robert Downey Jr. but I’m worried I’d just be like Chris Farley when he used to interview celebritiess on SNL
“Remember in the first Iron Man movie, when you put on the prototype suit and were hovering around the garage and figuring out how to control it, and at the end of the scene you said “Yeah, I can fly.” ? Remember that? That was awesome.”
My kitchen cabinets are in tough shape. Harrison Ford or Nick Offerman has some background in that area and I bet both would appreciate doing something with a fan completely unrelated to acting.
And no matter how they turn out I will tell everyone that walks in my house who did it.