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Hollywood's greatest leading men: A power ranking

James D. Morgan Archive

James D. Morgan

As any man, dude, bro, or other y-chromosome-dependent label will tell you, men are constantly searching for role models. For some of us, maybe that’s dad. For others, it’s musicians and athletes. For most, however, it’s Hollywood’s Leading Men, a 70-year legacy of style, skill, and charisma to not only marvel at, but mold and mangle and eventually, through force of sheer will and luck, make our own. Who you return to time after time—when you need an escape, a little confidence, or just a killer leather jacket—probably says a lot about you, but from Denzel to Leo, Brando to Dean, there are just some things you can’t debate. So without further ado, let’s do what our generation was born to do—argue about lists—and roll out the red carpet for the greatest leading men of all time. Andddddd action!

15. Brad Pitt

Essential Performances: Se7en, Fight Club, The Tree of Life

Best Remembered: Bare-knuckle boxing (shirtless, of course).

Don’t let those looks fool you. Pitt has always been more human than heartthrob, pairing his washboard abs with an artistic bent, serious range, and unforgettable characters over the course of his nearly three-decade career. Said abs definitely don’t hurt though…

14. Steve McQueen

Essential Performances: Bullitt, The Great Escape, The Getaway

Best Remembered: Driving things really fast.

The godfather of DIY stuntwork, McQueen drove his own cars, jumped his own motorcycles, and, perhaps most importantly, managed to make turtlenecks look badass. Needless to say, without McQueen, modern action stars like Tom Cruise and Harrison Ford simply wouldn’t exist.

13. George Clooney

Essential Performances: O Brother, Where Art Thou?; Good Night, Good Luck; The Descendants

Best Remembered: As a tequila baron.

Although Clooney’s resume may be a little uneven compared to those of his peers, there’s no denying he has it—pure unbridled star power bursting from every perfectly tailored seam of his Italian linen suits. He also possesses a secret weapon: Honest-to-goodness comedic chops, which count for a lot in the shamelessly soul-battering Hollywood landscape.

12. Samuel L. Jackson

Essential Performances: Pulp Fiction, Unbreakable, The Hateful Eight

Best Remembered: Munching on a Big Kahuna Burger.

Make no mistake: Sam Jackson has done some bonafide, put-this-DVD-in-the-microwave-for-the-good-of-mankind shit over the years. His performances when paired with director Quentin Tarrantino, however, alone warrant inclusion, frapping profanity, violence and one of the most intimidating personalities in film history into a bloody and beautiful thing.

11. James Dean

Essential Performances: Rebel Without a Cause, East of Eden, Giant

Best Remembered: Squinting and smoking, in that order.

If you were to evaluate James Dean’s career based simply on his pop cultural impact, you might assume he made dozens upon dozens of classics. The reality, however, is much different. Dean starred in only six hours of Hollywood movies before dying in a car accident in 1955, but 62 years later his star power still burns bright enough to give you a tan (not that Hollywood needs any help with that) .

10. Denzel Washington

Essential Performances: Malcom X, Training Day, Man on Fire

Best Remembered: Ruining Ethan Hawke’s life.

It’s not often that an actor’s breakthrough role is as important—and demanding—as Malcom X. That’s a character for seasoned veterans stepping out of their comfort zone in order to make one last awards season push. But such is the power of Denzel Washington, who used that 1992 turn as a launch pad for one of the most prolific, powerful, and diverse careers in modern Hollywood. It’s also doesn’t hurt that he has the voice of Zeus, but that’s a longer discussion for another time.

9. Robert De Niro

Essential Performances: Taxi Driver, Raging Bull, Goodfellas

Best Remembered: Shouting at himself in the mirror.

Bob is a bit of enigma. After years toiling in some of the darkest rolls Tinseltown could dream up, De Niro turned over a lighthearted leaf in the early aughts and never looked back—scathing reviews be damned. And although he deserves more comedic credit than he’ll ever get—his Meet the Parents performance is a classic—it’s for tough-talking roles like Jake LaMotta and James Conway that he will always, rightfully be remembered.

8. Clint Eastwood

Essential Performances: The Good, The Bad, and The Ugly; Dirty Harry; Unforgiven

Best Remembered: Glaring out from under the brim of a Stetson.

The ultimate steely-eyed badass, Eastwood didn’t need dialogue to make a big impact, preferring the power of a six shooter and a cigarillo instead. But while he will forever be known as a stoic assassin, Eastwood has more range than the prairies he used to frequent, starring in everything from Dirty Harry to the The Bridges of Madison County over the course of his 60 career.

7. Leonardo DiCaprio

Essential Performances: The Aviator, The Departed, The Revenant

Best Remembered: At the bow of the Titanic (come on, you can’t deny it).

Once Hollywood labels you a “pretty boy”, it’s only a matter of time before you’re spit out the bottom of the rom-com barrel. But not Leo. Somehow he managed to ride "dreamboat" rolls in Romeo + Juliet and Titantic and into the upper thespian echelon. An actor, celebrity, activist, and IDGAF style icon, DiCaprio—like Dean before him—is the dude by which his generation will be measured, and that says more than any monologue ever could.

6. Sean Connery

Essential Performances: From Russia With Love, Indiana Jones and the Last Crusade, The Rock

Best Remembered: Behind the wheel on an Aston Martin.

Sorry Roger Moore, but Sean Connery is THE James Bond—a scotch-swilling, tux-rocking alpha who is as much an embodiment of mid-century manhood as he is a British spy (Bond was never a very good spy anyway). Without this role, Connery—for all his gruff charm—probably doesn’t crack the top 50. With it, he’s a f—king icon.

5. Sidney Poitier

Essential Performances: In the Heat of the Night, Guess Who’s Coming to Dinner, Lillies of the Field

Best Remembered: Smashing paradigms like ice cubes.

In terms of impact on the filmmaking landscape, no man on this list can touch Sidney Poitier, a class act who obliterated Hollywood’s color barrier not because he set out to, but because he was so damn good he couldn’t be ignored. Without Poitier, stars like Denzel Washington and Samuel L. Jackson wouldn’t exist, and that is worth far more than some golden trophy on the mantel (though he has one of those, too).

4. Robert Redford

Essential Performances: Butch Cassidy and the Sundance Kid, All the President’s Men, Jeremiah Johnson

Best Remembered: As the founder of the influential film festival on earth.

Let’s just get this out of the way: Redford is an on-screen legend, putting together one of the single greatest film runs in Hollywood history in the late ‘60s and early ‘70s. With that said, his impact behind the curtain—as the founder of the Sundance Film Festival in 1978—is even more profound. The single most disruptive force in filmmaking since sound, Sundance singlehandedly made “indie” films a viable genre, opening up Hollywood to an entirely new world of creators and viewers alike.

3. Jack Nicholson

Essential Performances: One Flew Over the Cuckoo’s Nest, The Shining, The Departed

Best Remembered: Hacking into your nightmares with an axe.

Nicholson is at his best when he’s going just a little bit crazy. Throw him in a Nancy Meyers rom-com and he almost seems normal, but pair him with Kubrick or put him in the lead of Ken Kesey’s acid test opus, and the wheels come famously (and gloriously) off. It’s a shame most Gen Zs will probably know him (and Spike Lee, for that matter) as little more than NBA sideline grifters, but that doesn’t change the fact that Jack is the most namecheckable actor of all time. Full stop.

2. Paul Newman

Essential Performances: Cool Hand Luke, Butch Cassidy and the Sundance Kid, The Sting

Best Remembered: On a bottle of Balsamic Vinaigrette.

The dude played Cool Hand Luke and Butch Cassidy, had a Rolex named after him, and raced cars to relax. He also started his own food empire as a charity and pioneered dressing down as dressing up. Any objections?

1. Marlon Brando

Essential Performances: A Streetcar Named Desire, On the Waterfront, The Godfather

Best Remembered: As The Don.

If “I could have been a contender” isn’t the most quoted line in Hollywood history, then “I’m gonna make him an offer he can’t refuse” definitely is. The constant? Marlon Brando, who revolutionized acting by simply acting human. That may seem obvious now, but in 1955, as Brando, bedecked in flannel and denim, rubbed the back of his neck and mumbled his way into the hearts of women from Sunset Boulevard to Madison Avenue, he may as well have landed on the moon.