10. Trent Walker-Swingers
A quick-witted, good looking actor, Vince Vaughn made Trent the perfect man to shepherd his lonely friend who just can't let go of his previous relationship in Swingers. Trent is there at every turn to teach any and all of his friends how to handle every aspect of getting a lady while simultaneously working to rebuild the shattered ego of his friend. Trent is undoubtedly the alpha dog in this movie.
9. Axel Foley-Beverly Hills Cop franchise
When this street smart cop from Detroit finds himself in Beverly Hills, he's able to employ his natural charm and the tricks he learned along the way to outwit every other cop in the city. Prior to Eddie Murphy landing the role, Mickey Rourke and Sylvester Stalone almost brought the character that would make Murphy a star to the big screen. Though those two stared in several films that we love, it's the comedic timing and improvisational feel that Murphy brings to Foley that lands him on this list.
8. Tyler Durden-Fight Club
Tyler is one of the few who lives outside of the lifestyle of visceral men who want to break out of society's barriers that most of us comply with. As a result, he leaves the audience wanting to do the same during every viewing of Fight Club. Durden lives in a run down apartment that leaks and floods with brown water; yet somehow he leaves the audience envious of the life he lives. It could be his lack of compromise, or his ability to lead. Either way, he makes it all look cool.
7. James Bond-James Bond franchise
This spy genre of films is populated with characters who are trying to be cool. Whether it's gadgets, or his entire demeanor, James Bond is the best of them all because he doesn't need to try. Often considered one of the greatest film heroes ever, audiences can assume that Mr. Bond can save the day and get the girl in the end. To top things off, 007 always does things in style even over 20 films later.
6. Danny Ocean-Oceans trilogy
It took a huge amount of charm and presence for George Clooney's character to outshine Frank Sinatra's version. In the 2001 remake, Danny is the brains behind a group of criminals that manages to pull off the impossible. Danny rolls with whatever changes come his way, and always makes sure that everything works to his advantage. He's cool, calm, and collected through and through.
5. John Shaft-Shaft franchise
Shaft is the black private dick that's a sex machine to all the chicks, and we can all dig it. Whether it's the clothes he wore, the women he slept with, or the attitude, he made it clear that he's not one to be messed with. One thing's for certain; Shaft was is, and always will be the man.
4. Rick Blaine-Casablanca
"We'll always have Paris." And we'll always have rick Blaine thanks to this iconic romantic drama, and one of the greatest films of all time. As the owner of a high-class Morocco night club, he's jaded on the outside, but underneath the cool exterior is a man who's torn between love and virtue. With a sketchy background that adds to his mystique, Rick is the tough, but smart guy in a trench coat. He sticks his neck out for nobody, and is the envy of all other men. Here's looking at you Rick!
3. Jim Stark-Rebel Without a Cause
James Dean's short lived film career defined what is was to be cool for a generation. It was this character from the mid 50's drama that defined his legacy the most. The fact that the actor died in a high speed car crash shortly before the film was released put even more weight on Dean's shoulders. He portrayed a teen trying to make sense of the world he lives in, but in a unique, interesting way. James Dean made this character into one that we can relate to.
2. Han Solo-Star Wars
Luke Skywalker may be the ultimate hero of the Star Wars saga, but it's his friend Han that audiences always wanted to be. Han is a scoundrel with a heart of gold, and is always interested in making a quick buck. He'll also save the day along the way.
Honorable mentions:
Butch Cassidy-Butch Cassidy and the Sundance Kid
Crash Davis-Bull Durham
Jules Winnfield-Pulp Fiction
Jacob Palmer-Crazy, Stupid, Love
Ferris Bueller-Ferris Bueller's Day Off
1. Jeff "the Dude" Lebowski-The Big Lebowski
All he wanted to do was bowl, drink a White Russian, and get high. Instead the Dude finds himself in the middle of intrigue and violence. He does raise his voice in a scene or two, but the Dude is mostly relaxed and takes everything in stride. There's one thing that's for certain; the Dude abides, and we take comfort in that.
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