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Name a cooler dude than Cary Grant?

Dean Martin.

I’ll throw one out that nobody ever mentions….James Garner.

Yep. Garner's output isn't as large as the others, but movies like "Marlow" and "The Americanization of Emily", he is outstanding in them.

"Marlow" also happens to have the utterly delicious Rita Moreno playing a stripper...yes she's wearing a skin colored costume, but my gawd...yummy.
 
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The guy at the beginning of the line at OP’s mom’s house

Condom_Man.jpg
 
Bringing Up Baby is on TCM right now.
I love the scene where he and Hepburn are exchanging witty banter as he showers and she sits in the other room. Madcap antics occur, and as he steps into the living room dressed in a woman's robe and confronts the aging aunt and has to explain his appearance, he exclaims, "All of a sudden I decided to go GAY"!!!
 
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Yep. Garner's output isn't as large as the others, but movies like "Marlow" and "The Americanization of Emily", he is outstanding in them.

"Marlow" also happens to have the utterly delicious Rita Moreno playing a stripper...yes she's wearing a skin colored costume, but my gawd...yummy.
I have never seen anything with Garner in it that I didn’t like.

Another cool guy that hasn’t been mentioned…..Kurt Russell.
 
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CG was great and his style was upbeat and effortless and very likeable. i would suggest that robert downey jr and bruce willis in the current era are similar in those respects.
 
I actually love live theater. Back when we lived in La Jolla (San Diego) for several years we had season tickets to the La Jolla playhouse. We saw several shows that went onto Broadway and to win Tony awards like jersey boys, cry-baby, and Memphis.

On the stage you have to speak and move differently since most of the audience cannot see much in the way of facial expressions. But that just looks weird in film.

It looks weird because of how people view modern movies compared to what they were in the 30s/40s. Back then, they were, essentially, plays on film. As newer, at the time, directors came up watching movies while growing up, the movie experience transitioned, specifically in the 1950s/60s. It's a part of why movies by the late 60s started getting edgier. It's also why the Hays Code was pushed aside for the MPAA ratings.

Kind of like sports, it's impossible to compare what movies are now to what they were 80 years ago.
 
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Eastwood, before he became a whacknut. The entire cast of the Navarone movies, Dirty Dozen, the cast of Coccoon (the old dudes and Jessica Tandy). Don Ameche had a Burmeister/Coralville connection.
 
Johnny Cash. Dude had some issues, but man did he ever have fun on his own terms.

I've always thought Willie Nelson was a cool dude also. I guess those two are pretty similar in their FU attitudes/actions. Always appreciate that in people.
 
Clint Eastwood.
I dunno, man. Clint Eastwood seems like an asshole. Maybe that's part of being cool? I'm not questioning his acting talent and/or directing skills. But, Clint has rubbed a lot of people the wrong way!
 
I dunno, man. Clint Eastwood seems like an asshole. Maybe that's part of being cool? I'm not questioning his acting talent and/or directing skills. But, Clint has rubbed a lot of people the wrong way!
I was just talking on screen. I have no idea what these people are like in real life(and don't care, for the most part).

Edit: This is why I chose a celebrity as my answer in the first place. If we're talking day to day, there is a fella who works in the drive thru at Checkers by my work that seems like a pretty cool fella.
 
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I've been on a tear watching Grant's films lately. I watched The Awful Truth which paired Grant up with Irene Dunne and Ralph Bellamy, and Holiday which featured an electric combination of Grant and Katherine Hepburn.
The guy was suave as can be, witty... He lived the high life in the golden age of Hollywood.
I am willing to entertain suggestions as to who was a cooler dude.
And, CSB, he died in Davenport. I did not know that until I was doing some research on those movies. Grant was in his 80s and doing some one man shows, and while in Davenport he suffered a stroke. He refused treatment, and passed away several hours later. Many believe he'd grown despondent over the death of so many contemporaries in the previous years, and that is why he refused advanced care the day he suffered the stroke.
Watch "Bringing up Baby" with Grant and Hepburn. A really funny movie.
 
Watch "Bringing up Baby" with Grant and Hepburn. A really funny movie.
I’ve seen it. TCM had it on today, and I stopped what I was doing to watch about 30 minutes of it.
Grant had a natural talent for improv and for blending in with some talented leading ladies.
 
Kris Kristofferson:

Oxford scholar
Golden Gloves
Army Ranger
Actor - A Star is Born
Singer - including in The Highwaymen with Willie and Waylon and Johnny
Wrote “Sunday Morning Coming Down” and “Me and Bobby McGee”

That’s pretty cool.
 
This dude would kick everyone's ass mention so far and would look good doing it.

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