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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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Give Back

Last-Minute Holiday Gift Guide

Hits from the '80s are on repeat all Christmas Eve and Day on IFC.

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GIFs via Giphy, Photos via The Everett Collection

It’s the final countdown to Christmas and thanks to IFC’s movie marathon all Christmas Eve and Christmas Day, you can revel in classic ’80s films AND find inspiration for your last-minute gifts. Here are our recommendations, if you need a head start:

Musical Instrument

Great analog entertainment substitute when you refuse to give your kid the Nintendo Switch they’ve been drooling over.

Breakfast In Bed

Any significant other or child would appreciate these Uncle Buck-approved flapjacks. Just make sure you’re not stuck on clean up duty.

Cocktail Supplies

You’ll need them to get through the holidays.

Dance Lessons

So you can learn to shake-shake-shake (unless you know ghosts willing to lend a hand).

Comfy Clothes

With all the holiday meals, there may be some…embigenning.



Get even more great inspiration all Christmas Eve and Day on IFC, and remember…

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A-O Rewind

Celebrating Portlandia One Sketch at a Time

The final season of Portlandia approaches.

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GIFs via Giphy

Most people measure time in minutes, hours, days, years…At IFC, we measure it in sketches. And nothing takes us way (waaaaaay) back like Portlandia sketches. Yes, there’s a Portlandia milepost from every season that changed the way we think, behave, and pickle things. In honor of Portlandia’s 8th and final season, Subaru presents a few of our favorites.

via GIPHY

Put A Bird On It

Portlandia enters the pop-culture lexicon and inspires us to put birds on literally everything.

Colin the Chicken

Who’s your chicken, really? Behold the emerging locavore trend captured perfectly to the nth degree.

Dream Of The ’90s

This treatise on Portland made it clear that “the dream” was alive and well.

No You Go

We Americans spend most of our lives in cars. Fortunately, there’s a Portlandia sketch for every automotive situation.

A-O River!

We learned all our outdoor survival skills from Kath and Dave.

One More Episode

The true birth of binge watching, pre-Netflix. And what you’ll do once Season 8 premieres.

Catch up on Portlandia’s best moments before the 8th season premieres January 18th on IFC.

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WTF Films

Artfully Off

Celebrity All-Star by Sisters Weekend is available now on IFC's Comedy Crib.

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Sisters Weekend isn’t like other comedy groups. It’s filmmaking collaboration between besties Angelo Balassone, Michael Fails and Kat Tadesco, self-described lace-front addicts with great legs who write, direct, design and produce video sketches and cinematic shorts that are so surreally hilarious that they defy categorization. One such short film, Celebrity All-Star, is the newest addition to IFC’s Comedy Crib. Here’s what they had to say about it in a very personal email interview…

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IFC: How would you describe Celebrity All-Star to a fancy network executive you just met in an elevator?

Celebrity All-Star is a short film about an overworked reality TV coordinator struggling to save her one night off after the cast of C-List celebrities she wrangles gets locked out of their hotel rooms.

IFC: How would you describe Celebrity All-Star to a drunk friend of a friend you met in a bar?

Sisters Weekend: It’s this short we made for IFC where a talent coordinator named Karen babysits a bunch of weird c-list celebs who are stuck in a hotel bar. It’s everyone you hate from reality TV under one roof – and that roof leaks because it’s a 2-star hotel. There’s a magician, sexy cowboys, and a guy wearing a belt that sucks up his farts.

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IFC: What was the genesis of Celebrity All-Star?

Celebrity All-Star was born from our love of embarrassing celebrities. We love a good c-lister in need of a paycheck! We were really interested in the canned politeness people give off when forced to mingle with strangers. The backstory we created is that the cast of this reality show called “Celebrity All-Star” is in the middle of a mandatory round of “get to know each other” drinks in the hotel bar when the room keys stop working. Shows like Celebrity Ghost Hunters and of course The Surreal Life were of inspo, but we thought it
was funny to keep it really vague what kind of show they’re on, and just focus on everyone’s diva antics after the cameras stop rolling.

IFC: Every celebrity in Celebrity All-Star seems familiar. What real-life pop personalities did you look to for inspiration?

Sisters Weekend: Anyone who is trying to plug their branded merch that no one asked for. We love low-rent celebrity. We did, however, directly reference Kylie Jenner’s turd-raison lip color for our fictional teen celebutante Gibby Kyle (played by Mary Houlihan).

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IFC: Celebrity seems disgusting yet desirable. What’s your POV? Do you crave it, hate it, or both?

Sisters Weekend: A lot of people chase fame. If you’re practical, you’ll likely switch to chasing success and if you’re smart, you’ll hopefully switch to chasing happiness. But also, “We need money. We need hits. Hits bring money, money bring power, power bring fame, fame change the game,” Young Thug.

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IFC: Who are your comedy idols?

Sisters Weekend: Mike grew up renting “Monty Python” tapes from the library and staying up late to watch 2000’s SNL, Kat was super into Andy Kaufman and “Kids In The Hall” in high school, and Angelo was heavily influenced by “Strangers With Candy” and Anna Faris in the Scary Movie franchise, so, our comedy heroes mesh from all over. But, also we idolize a lot of the people we work with in NY-  Lorelei Ramirez, Erin Markey, Mary Houlihan, who are all in the film, Amy Zimmer, Ana Fabrega, Patti Harrison, Sam Taggart. Geniuses! All of Em!

IFC: What’s your favorite moment from the film?

Sisters Weekend: I mean…seeing Mary Houlihan scream at an insane Pomeranian on an iPad is pretty great.

See Sisters Weekend right now on IFC’s Comedy Crib

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