Conventional wisdom (aka pop culture) suggests that coolness fades as a person gets older. I entirely disagree, but that’s a subject for another thread.
Septuagenarian Adam West (Batman) gets my vote as really cool–the kind of guy I would really enjoy shooting the breeze with over lunch or golf. Paul Newman is an obvious pick, but I’m looking for others.
Ian McKellen seems like he’d be fun to party with if you can keep up. Hugh Downs was going on archaeological digs and swimming with sharks, both just for fun, when he was well over 70 (it was in an interview with him some years ago) and until emphysema and a long neglected body slowed him down Kurt Vonnegut seemed to get new wind after he was 60 as did Studs Terkel, who in interviews in his 80s seemed as pissed off as ever. Helen Thomas, a fixture at every White House press conference since James A. Garfield, is still the wrath of God in her 80s as well.
Patrick Stewart, without a doubt. I think I’ve had a crush on him since I was about sixteen. I’d love to have a conversation with him, just to hear that voice in person, but I know I’d be all twitterpated and wouldn’t remember a second of it.
Paul Newman. Not only is he cool, I, not even 25 years old, would still do him.
Also, Sean Connery, Peter O’Toole (I was hoping he could be the replacement Dumbledore, but perhaps he’s too drunk), I still get hot for Harrison Ford (all that Indy Jones as a kid did me in, I imagine) Raquel Welch (how you get to be 60 and still be unbelievably hot, I would like to know) and Eartha Kitt. I love Eartha Kitt. And Sophia Loren.
And God help me, I’d love to hang with Shatner, Takei, and Nimoy.