A few years ago Blythe Danner and I passed each other crossing 5th Ave. We held eye contact for a few seconds and she gave me a big smile that made me feel like I probably had a chance. I was 38 and she was 65 at the time.
You’re conflating celebrity with being a performer, rather than just famous/celebrated. Stephen Hawking’s a celebrity, but I doubt he plays on his desirability.
I’ve long been a nut-magnet, so any female celeb that’s mentally unstable/damaged would find me irresistible.
Come to think of it, I was once personally thanked by one of the Wilson sisters (of Heart) for having bought a ticket to one of their concerts, but I’m pretty sure that was just politeness. On that particular day, I was in ratty clothes and messed up hair that made me look a bit like Napoleon Dynamite.
Looks like we’re going to have a cat fight over Wilfred Brimley. Not something that I would ever have thought I’d write, but the SDMB is wonderful that way.
As for me, I think I did have a chance with Tracy Bonham. She invited me backstage after a show once in 2000 to use the club’s hot tub with her. Unfortunately for me (and most-likely thankfully for her), I was active duty Navy at the time and literally had to be back on the ship within 45 minutes.
If I’m reading this correctly, the idea is who would you click with personality-wise if you were very wealthy and physically attractive? I’m going to go with Vince Vaughn. He was the first one to pop into my head, but I’ll try to explain my rationale:
(1) I like weight lifting, and men with muscle. He looks strong, but not obsessed with having chiseled abs. I bet we could talk about lifting together.
(2) I’ve heard he’s one of the more politically conservative men in Hollywood. I’m not super-conservative, but probably more conservative than most celebrities.
(3) He comes across as reasonably intelligent, but not very geeky. I like intelligence, but not really into geekiness.