Coolest Actors Who Deserve an Oscar (But Will Never Get One)

We may love these guys, but the Academy sure doesn’t

We may love these guys, but the Academy sure doesn’t

Winning an Oscar is a delicate art. Actors have to be popular, but respectable. Well-spoken, but not boring. Handsome, but also kind of ugly in a Philip Seymour Hoffman kind of way. And a little talent helps. But if that was all that mattered, the following actors and all-around awesome dudes would have already won. Sadly they’re destined to a lifetime of gracious loser cutaway shots. Guys, if it’s any consolation, you’re invited to our after party. (Bring taco shells and taco meat and napkins.)

Robert Downey Jr.

Nominated: Best Actor for Chaplin, Best Supporting Actor for Tropic Thunder

Photo: Merie Weismiller Wallace/DreamWorks | Licensed to Alpha Media Group 2012

Is there anything this guy can’t do? Win an Oscar, obviously. Perhaps he’s too cool, funny, and charming for the Academy to fully embrace. Even his more dramatic performances tend to have shades of humor or lightness, and we all know the Academy takes to comedy like a Fudgesicle to a hot tub. (Fudgescile is what we call our pet hamster.)

Oscar Advice: Get older. They didn’t give The Dude his Oscar until he grew up and swapped out his White Russians for straight whiskey, broken dreams and a geeeetar.

Woody Harrelson

: Best Actor for The People vs. Larry Flynt, Best Supporting Actor for The Messenger

Photo: Warner Bros./Everett Collection | Licensed to Alpha Media Group 2012

Why won’t he win? He’s a tad too crazy to be taken seriously. He’s known for playing psychos and nutjobs on screen (Natural Born Killers, 2012), and loves pot more than Lil Wayne. To add to the crazy, his hitman dad assassinated a federal judge and died in 2007 inside a supermax prison. (The judge’s last name was Wood. Woody…Wood? Weird, right?) Maybe the Academy is too afraid of controversy.

Oscar Advice: Lose the accent. Woody’s trademark Texas drawl reminds us too much of his character on Cheers. Accents are also what keep John Ratzenberger and George Wendt off the Academy’s red carpet.

Edward Norton

: Best Supporting Actor for Primal Fear, Best Actor for American History X

Photo: Mary Evans/Everett Collection | Licensed to Alpha Media Group 2012

This guy came out blazing in the mid-90s in movies like American History X and Primal Fear. He proceeded to lose Oscars to Roberto Benigni and Cuba Gooding Jr. And since those two are now triple-A superstars, it’s no wonder that Eddie feels slighted. It doesn’t help Norton’s case for credibility that he’s headlined a bunch of forgettable movies over the last eight years. Do you remember Leaves of Grass, The Painted Veil or Stone? Shut up! We’re trying to make a point. Just say “no.”

Oscar Advice: American History XX: I’m Racist Again. There’s no shame in going back to the well, Mr. Norton.

Clive Owen

: Best Supporting Actor for Closer

Photo: Universal/Everett Collection | Licensed to Alpha Media Group 2012

No one took him seriously when he was on his prestigious indie kick – Gosford Park, Closer, Children of Men – and they certainly won’t now that he seems to have accepted his fate of endless Bond auditions and action movies.

Oscar Advice: Change your name. Clive Owen is too British and stuffy. How about Panther Bigsby? With a name like Panther Bigsby no one will refer to you as, “That British guy who’s in all those movies? No, not Jude Law. The other one? I think his name is Collin…Rollin? Whatever.” 

Johnny Depp

: Best Actor for Pirates of the Caribbean: The Curse of the Black Pearl, Best Actor for Finding Neverland, Best Actor for Sweeney Todd: The Demon Barber of Fleet Street

Photo: Twentieth Century Fox/Everett Collection | Licensed to Alpha Media Group 2012

A lot of people maintain that Johnny Depp should’ve gotten Oscar nods for his early Tim Burton movies, like Edward Scissorhands. But those movies encapsulate why Johnny is never going to win over the Academy: He’s just too weird. They tried to get behind him when he toned it down for a blockbuster franchise – Pirates of the Caribbean: Curse of the Black Pearl was his first nomination ever – but they gave up when he decided he was just going to keep making those movies until he had enough money to buy France and convert it into a stop motion Burton fever dream. Only with way more baguettes.

Oscar Advice: Go normal. Instead of playing eccentric characters, play a normal guy named Timmy Miller who wears cargo pants and eats at Red Lobster. Trust us. This will work.

Don Cheadle

: Best Actor for Hotel Rwanda

Photo: TriStar Pictures/Everett Collection | Lilcensed to Alpha Media Group 2012

The Hotel For Dogs actor probably never won an Oscar because despite the Hotel for Dogs actor’s amazing roles in Hotel Rwanda and Boogie Nights, the Academy knew that the Hotel for Dogs actor would one day star in Hotel for Dogs and they didn’t want to run the risk of tainting the Academy’s name with the following ad: “Hotel for Dogs is dog-gone good! Staring Academy Awarding winning Don Cheadle. For reals! Arf!” 

Oscar Advice: Play a sassy, Southern, world-weary ghost who teaches a young boy about tolerance and life. Not sure where to find such a role? May we offer you our script for Ghost Guy.

Sam Rockwell

: Never

Photo: Mark Tille/Sony Pictures Classics | Licensed to Alpha Media Group 2012

He’s a little too indie – for evidence see Moon, one of the best movies of 2009 which went largely unrecognized. (Also unrecognized? His groundbreaking work as a villain who nefariously sips Coke from a really long straw in Charlie’s Angels.) Rockwell probably has a better shot at a Tony, considering his blossoming bromance with crazy-ass playwright and sometimes director Martin McDonagh .

Oscar Advice: Ask Cheadle about this Ghost Guy movie. You’d be perfect for the female lounge singer trapped in the body of a ’70s police detective named Chuck Gator.

Alan Rickman

: Never

Photo: Warner Bros. PIctures | Licensed to Alpha Media Group 2012

This man has given us Hans Gruber, Severus Snape and the blueprint for the world’s greatest GPS. What has the Academy given him in return? Not even an invitation. It doesn’t help that the Oscars are definitely Team Amurrica – only 12 Brits have won Best Actor or Best Supporting Actor since 1980 – or that many of Rickman’s movies fall in the action, sci-fi or fantasy genres rather than the old-alcoholic-has-been-forms-unlikely-friendship-or-reconnects-with-his-children genre. Sadly, the closest poor Al is likely to get to an Oscar is an eventual appearance in the memorial montage, scored to a particularly somber “Snape. Snape. Sev-er-us Snape.”

Oscar Advice: American remake of Love Actually entitled Love Totally.

Harvey Keitel

: Best Supporting Actor for Bugsy

Photo: Everett Collection | Licensed to Alpha Media Group 2012

He was awesome in Mean Streets, Taxi Driver, Reservoir Dogs and, of course, Sister Act, but all the Academy’s ever done is throw him a measly nod for Bugsy back in the ’90s. Clearly they think their work here is done.

Oscar Advice: Come back to life. (We assume he’s dead.)

Peter O’Toole

: Best Actor for Lawrence of Arabia, Best Actor for Becket, Best Actor for The Lion in Winter, Best Actor for Goodbye Mr. Chips, Best Actor for The Ruling Class, Best Actor for The Stunt Man, Best Actor for My Favorite Year, Best Actor for Venus

Photo: Everett Collection | Licensed to Alpha Media Group 2012

With eight nominations and zero wins under his belt, Peter O’Toole is definitely the bridesmaid of the Oscars. He technically received an honorary award in 2003, but we all know that’s just a “Dude, you’ve been in a lot of movies and you’re super old. Congrats!” certificate of achievement no one wants.

Oscar Advice: Yeah, um…not gonna happen Pete. Perhaps you should aim for the Documentary Short Subject award. They hand those things out like Halloween candy.

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