7 Times Leonardo DiCaprio Should Have Won an Oscar

Leo DiCaprio

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It’s crazy to think that Leonardo DiCaprio has been acting professionally since the age of five (he got kicked off the set of Romper Room!) but has yet to take home an Academy Award. The dude’s been in some of the most financially successful and critically lauded movies of all time. What’s it gonna take? Join us on a trip through history as we spotlight seven flicks that Leo should have taken home an Oscar for.

7. What’s Eating Gilbert Grape

DiCaprio’s breakthrough role came as the developmentally disabled teen Arnie in Lasse Hallstrom’s small-town drama. It’s really tough to play a role like this, but the critics unanimously raved over Leo’s methodical inhabiting of the character. He got his first Oscar nomination, but lost to Tommy Lee Jones in The Fugitive. Much respect to Tommy Lee, but that’s highway robbery.

6. The Aviator

Playing a famous historical figure is usually a pretty good in for Oscar recognition, and DiCaprio stunned critics with his transformation into film producer and aviation pioneer Howard Hughes. The Aviator was nominated for a staggering 11 Oscars, taking home five of them. Jamie Foxx won the Best Actor statue for Ray, which in hindsight seems pretty crazy, especially considering the trajectory of both mens’ careers since then.

5. Inception

Keeping Christopher Nolan’s brain-twisting tale of mental invasion and memory relatable for the mass audience is a tough task, but DiCaprio’s performance as Dom Cobb made it all possible. Inception was the most ambitious movie of 2010, truly pushing the envelope for what the cinematic medium could portray. Sadly for Leo, Jeff Bridges took the Oscar for playing an alcoholic country singer in Crazy Heart. What can we say? The Academy loves drunks.

4. The Wolf Of Wall Street

DiCaprio was actually nominated for his role as producer on Jordan Belfort’s coke-addled memoir turned wild Scorsese movie, but I think that he should have taken home the statue for his work in the lead. As Leo slides into his “dad bod” phase, he owns the stereotype of a dissolute party boy steadily destroying both his body and his reputation. His turn as Belfort was terrifyingly believable. Unfortunately he lost the Best Actor trophy to co-star Matthew McConaughey.

3. Django Unchained

Christoph Waltz took the Best Supporting Actor statue for his role in Quentin Tarantino’s spaghetti Western homage. Shockingly, DiCaprio wasn’t even nominated for his chilling turn as vile plantation owner Calvin Candie. It’s a shame, because it was a meaty supporting role that allowed Leo to deliver one of his best performances in years. Hopefully he’ll channel his inner bad guy again in the future.

2. Revolutionary Road

Sam Mendes’ moving depiction of a married couple falling apart in 1960s suburbia reunited Leo and his Titanic costar Kate Winslet and earned them both critical acclaim and a Golden Globe win for Winslet. While costar Michael Shannon scored an Oscar nom, Leo came up empty when it came to awards season gold.

1. The Departed 

This acclaimed Boston-set crime flick took home four Oscars, including Best Picture and a much-deserved win for director Martin Scorsese. Of the stellar cast, only Mark Wahlberg was nominated for Best Supporting Actor. Leo was unjustly shut out for his performance as undercover police officer Billy Costigan.

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Documentary Now! Robert Evans Mansion

The Reel Deal

Everything You Need To Know About “Mr. Runner Up” Inspiration Robert Evans

Watch the two-part finale of Documentary Now! this Wednesday at 10P on IFC.

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Photo Credit: Everett Collection

In its upcoming two-part finale, Documentary Now! spoofs the crown jewel of docs: The Kid Stays In The Picture. It’s the autobiographical documentary about Robert Evans, the unlikely Hollywood mogul whose mix of self-aggrandizing bravado, classic good looks and extremely circumstantial good luck took him from being a salesman to an actor to the head of Paramount Pictures.

If you’ve never seen the film, it’s totally worth it. Rotten Tomatoes agrees, with a staggeringly-high approval rating. Watch it before, or watch it after — doesn’t matter. You’ll appreciate it whenever.

In the meantime, here’s a bit of background that will come in handy…

Robert Loves Robert

Robert Evans desk

USA Films/Everett Collection

Robert Evans is the ultimate Robert Evans fan. The movie was written, produced, directed and narrated by Robert Evans. It is totally unbiased.

He’s Kind Of A Big Deal

Robert Evans, Chinatown
Paramount Pictures

Evans produced some of Hollywood’s true classics: Chinatown, Rosemary’s Baby, The Godfather, Love Story…the list goes on. Totally legit and amazing movies.

He’s Also Kind Of A Joke

Wag The Dog
New Line Cinema

Evans has been parodied in TV shows and movies like Entourage and Wag The Dog. He is the quintessential “producer” you already have in your head.

So Wrong He’s Right

Robert Evans Slap
20th Century Film Corp

Robert Evans is a notorious narcissist whose love of self is so blind and sincere that it’s actually adorable.

There’s Something Missing

via Giphy

Entire sections of Robert Evans’ life are left out of the documentary. Maybe it’s because of timing. Maybe it’s because real life isn’t a tidy narrative. Who knows.

He Blew It

Spider coke

Evans had a pretty spectacular fall from grace. He was convicted of cocaine trafficking in the early 80’s, and was connected to a contract killing during the production of The Cotton Club. Oops.

Losing Is For Losers

Everett Collection
Everett Collection

In the Robert Evans mythology, all tragedies are just triumphs in disguise, and every story has a happy ending…for Robert Evans.

Bill Hader Jerry Wallach

With these simple facts in hand you are now prepared to thoroughly enjoy the two-part finale of Documentary Now! starting this Wednesday at 10/9c on IFC.

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Weird Roles

Anthony Michael Hall’s Most Rotten Movies

Catch Anthony Michael Hall in Weird Science on Friday at 8P on IFC.

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Photo Credit: Universal/Everett Collection

Anthony Michael Hall was the quintessential ’80s nerd. We love him in classics like The Breakfast Club and National Lampoon’s Vacation. But even the brainiest among us has his weak spots. In honor of Weird Science airing this Rotten Friday, we analyze Hall’s worst movies.

Weird Science (1985) 56%

A low point for John Hughes, Weird Science is way too wacky for its own good. Anthony Michael Hall’s Gary and his pal Wyatt (Ilan Mitchell-Smith) create the “perfect woman.” Supernatural chaos ensues. The film costars a young Bill Paxton, floppy disks, and a general disconnect from all reality.

The Caveman’s Valentine (2001) 46%

This ambitious drama starring Samuel L. Jackson couldn’t live up to its rich premise. Jackson plays Romulus, a Juilliard-educated, paranoid schizophrenic who lives in a cave. Hall co-stars as Bob, a rich man, who wants to see Romulus play the piano. The plot centers around Romulus investigating a murder, but with so much going on, the movie never quite finds its rhythm.

All About the Benjamins (2002) 30%

Ice Cube plays a bounty hunter who teams up with Mike Epps’ con man to catch diamond thieves. Hall plays Lil J, a small-time drug dealer. It’s definitely a role we’ve never seen Hall in, but overall the movie isn’t funny or original enough to justify its violence.

Freddy Got Fingered (2001) 11%

This showcase for Tom Green’s goofy gross-out comedy is often hailed as one of the worst films of all time. Green plays Gord, a 20-something slacker, who dreams of having his own animated series. Hall is Dave Davidson, a CEO of an animation studio who eventually helps Gord find success. Too bad Tom Green wasn’t so lucky.

Johnny Be Good (1988) 0%

Hall plays against type as Johnny Walker, a star quarterback. Robert Downey Jr. is his best friend and Uma Thurman plays his devoted girlfriend. Despite the support of a future A-list cast, the movie lacks central conflict and charm. Or, as TV Guide put it, “Johnny be worthless.” Ouch.

Catch the “Too Rotten to Miss” Weird Science this Friday at 8P on IFC.

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Season 6: Episode 1: Pickathon

Binge Fest

Portlandia Season 6 Now Available On DVD

The perfect addition to your locally-sourced, artisanal DVD collection.

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End of summer got you feeling like:

Portlandia Toni Screaming GIF

Ease into fall with Portlandia‘s sixth season. Relive the latest exploits of Fred Armisen and Carrie Brownstein’s cast of characters, including Doug and Claire’s poignant breakup, Lance’s foray into intellectual society, and the terrifying rampage of a tsukemen Noodle Monster! Plus, guest stars The Flaming Lips, Glenn Danzig, Louis C.K., Kevin Corrigan, Zoë Kravitz, and more stop by to experience what Portlandia is all about.

Pick up a copy of the DVD today, or watch full episodes and series extras now on IFC.com and the IFC app.

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