First off, I'm extremely glad that @VinMcCarthy made this challenge because this is one of those random survey-style questions I always think about.
Well, this one, and the one where you're a convict on death row and you get to pick your last meal. (The answer, obviously, would be a bottomless mimosa brunch buffet.)
But if I had to pick three people to eat dinner with, it would be (in no particular order): Amy Poehler, Cher, and Andre 3000.
Andre Benjamin is the coolest guy on planet Earth right now. (And if not, he is the prototype.) I grew up listening to a ridiculous amount of Outkast, particularly ATLiens and Southernplayalisticadillacmuzik. Andre always stuck out as something more than an MC. He's a true artist with unique style that transcends into everything he does - whether it's in a record studio, on the runway, or playing on the movie screens.
Speaking of people that are cooler than being cool, I am obsessed with Cher. She's like the fun, cool aunt that I never had growing up. (Sorry, Aunt Sue.) Her life has just been so INTERESTING, plus she's sharp as a tack, so I'd love to be able to sit down to dinner with her and bask in the glow of her witticisms. Also, here's a secret about me: I have a killer Cher impression, and I'd love to have a 'Cher-off' duet with her one day.
I used to HATE Amy Poehler. Back during SNL and the 'Baby Mama' era, she felt a bit obnoxious and a little unauthentic. But then she came into her own as a comedienne, and I fell in love. Her book, "Yes, Please", was like receiving advice from someone who understood me. Every chapter have leave me shouting "Holy crap, this is my LIFE." I'd like to thank her for being the voice of ambitious 'smart girls' (over dinner, of course).