Leslie Nielsen–Anyone who can transition from drama to slapstick comedy has to be a pretty cool dude.
Jack Palance–'Nuff said.
(seconded…no, thirded…) Sam Elliott
Christopher Lee.
Michael Caine
Tommy Lee Jones
Gene Hackman
Dominic Chianese (Uncle Junior on The Sopranos)
Robert Loggia
Yeah, but you have to figure that his mustache is nearly as old, if not older, so the total sum of their ages easily qualifies him.
Donald Sutherland’s pretty cool, and he’s Canadian. But my vote would definitely have to go for Sir Ian McKellan (or possibly Christopher Lee).
Hector Elizondo. At 69 he makes me go all droolish. Robert Reford - not because he’s physically aged well, he hasn’t. But because he seems to care for a lot of things outside himself.
StG
How 'bout it. Another one I’d do without hesitation.
I’d like to hang out and have a few beers with Gene Hackman or Morgan Freeman. And I bet Eli Wallach would have some good stories to tell about working with practically everyone. It’s a pity Robert Mitchum bit the dust some time ago; I’d love to hear him say, “Build my gallows high, baby,” in real life.
As for women still attactive into their sixties, I’m going to pick Dames Helen Mirren and Diana Rigg.
Talking about actors who are too cool to care about their shitty films, Michael Caine has to be at the top of the heap; his comment about Jaws: The Revenge (“I have never seen it, but by all accounts it is terrible. However, I have seen the house that it built, and it is terrific.”) takes the prize. Donald Sutherland is a close runner up. Harrison Ford, on the other hand, just seems…confused, as if he’d like to make a good film once in a while, but can’t seem to get around to actually reading a script. As far as I’m concerned, he retired his talent hat after The Fugitive, and he wasn’t even the best actor in that film.
Stranger
Even a tired and emotional deputy leader of Britain’s Labour Party. (See the “Personal Problems” section here, also the “Foreign Secretary” section for the origin of “tired and emotional.”)
Michael McKean is still plenty cool, but he won’t turn 60 until October of next year.
Trophy girlfriends are uncool now? 
They display a certain insecurity that is uncool.
Eh, fair enough. He still rescues people in his helicopter.
Yeah, but Michael Caine is…Michael Caine.
Not many people know that.
Stranger
No he’s not. 
I thought Michael Caine was Sir Maurice Mickelwhite…
An explanation for the coolness of our older generation. People in their sixties were in their twenties and thirties during the 1960s, when many many young people broke from the traditions of the WWII generation. Even those celebrities who define themselves as conservative are conservative by today’s standards. In the 50s they’d be considered “out there” on the fringe in many ways.
Plus, so many older men and women (not just celebrities) are much more health conscious than their chain-smoking red meat eating parents and grandparents. They just look cooler.
IMHO
Sir Rhosis
Robert Duvall and Gene Hackman are in a category all their own for me 
Nobody deserves a name like that…not even someone who starred in Blame It On Rio.
Stranger