The Most BULLSHIT (!!) Oscar Wins of the Last 25 Years

Year: 2005
Category: Best Picture
What Should’ve Won? Brokeback Mountain

The most notorious bad Oscar win of my lifetime was when Crash, the paper-thin treatise on racial politics in Los Angeles that wound up laying a blanket of absolution over everyone with the comforting lullaby that everyone is a little bit racist, beat the groundbreaking gay romance of Brokeback Mountain. (Or, for that matter, Steven Spielberg’s provocative Munich, or the chilly and committed Capote, or the topical history lesson Good Night and Good Luck.) Even presenter Jack Nicholson looked shocked that Ang Lee’s Best Director win didn’t portend a Brokeback Best Picture victory. Almost immediately, the backlash hit Crash, and it hasn’t let up.

Where to stream Crash

Year: 2003
Category: Best Supporting Actor
Who Should’ve Won? Benicio Del Toro, 21 Grams

The 2003 Oscar race among supporting actors was a strange one. The critical champ, Peter Sarsgaard in Shattered Glass, was surprisingly absent, as was the one guy everybody kept assuming would turn up in the lineup eventually, The Lord of the Rings‘s Sean Astin. Tim Robbins was settled on as the compromise choice incredibly quickly, and he ended up winning all the major prizes that year, from the Globes to the SAGs to the Oscars. This all happened, seemingly, without anyone to stop and realize that Robbins … is kind of bad in Mystic River. The problem was that he was up against a series of great performances in mediocre movies like Ken Watanabe in The Last Samurai and Benicio Del Toro in 21 Grams.

Where to stream Mystic River

Year: 2010
Category: Best Director
What Should’ve Won? David Fincher for The Social Network

As a movie, The King’s Speech is not bad. It’s well acted; it’s a decently engaging story; it’s inspirationally stirring here and there. The big problem was that it triumphed in such a stacked Best Picture field, with The Social Network, Black Swan, Inception, and The Fighter as competition. Best Director is where it gets galling, though, both because Hooper’s direction is not the best thing about The King’s Speech, and because the names he beat out included Fincher, Aronofsky, David O. Russell, and the Coen brothers.

Where to stream The King's Speech

Year: 1997
Category: Best Supporting Actress
Who Should’ve Won? Julianne Moore, Boogie Nights

At the time, I was a giant L.A. Confidential fan and was just happy to see it win something over Titanic. But as the years go by, Basinger’s performance as Lynn Bracken gets more cosmetic and circumstantial. Meanwhile, performances like Julianne Moore’s in Boogie Nights shine all the brighter. Moore was able to win an Oscar, at long last, in 2014 for Still Alice, but that doesn’t help Minnie Driver any! Or Joan Cusack! Both of these gorgeous creatures have since gone Oscar-less, while Basinger … made I Dreamed of Africa. And was really terrible in 8 Mile!

Where to stream L.A. Confidential

Year: 1996
Category: Best Actor
Who Should’ve Won? Tom Cruise, Jerry Maguire

After losing for his performances in Jerry Maguire and, three years later, Magnolia, Tom Cruise seems to have stopped trying to win Oscars with his movies. Which is too bad, because, though he’s a far cry from Olivier, he’s the kind of risk-taking movie star who should have won an Oscar. As should, frankly, Ralph Fiennes, who gave a great performance in the dominant Best Picture winner, The English Patient, and yet still couldn’t pull it off in Best Actor. The other two nominees — Woody Harrelson for The People vs. Larry Flynt and Billy Bob Thornton in Sling Blade — were also excellent. So while Geoffrey Rush wasn’t even bad in Shine, he still managed to win for the biggest, hook-iest, Oscar-bait-iest performance. Also, great romantic comedy performances never win! A Tom Cruise win for Jerry Maguire would have been a standard-bearer for an entire genre!

Where to stream Shine

Year: 1995
Category: Best Picture
What Should’ve Won? Apollo 13

Braveheart SUCKS! Mel Gibson SUCKS! Honestly, the Best Picture category that year ended up being a little hinky, with Harvey Weinstein barnstorming Il Postino into the proceedings. But any of the other three films, from Ang Lee’s Sense and Sensibility to Ron Howard’s Apollo 13 to the pop-cultural sensation that was Babe would have made for better winners than Mel Gibson’s orgy of tartan-clad violence. 21 years later, Gibson would end up back in the Best Picture race for Hacksaw Ridge but some of us never dropped that grudge.

Where to stream Braveheart

Year: 1998
Category: Best Actor
Who Should’ve Won? Ian McKellen, Gods and Monsters

The ultimate triumph of glad-handing hype over any kind of substance. Roberto Benigni blazed a path through the 1998 awards season, playing the hyper-active, semi-fluent Italian transplant whose happy little clown movie about dancing your way through Auschwitz was becoming the toast of the establishment town. Meanwhile, Ian McKellen and Nick Nolte were giving career-highlight over there in Gods and Monsters and Affliction. But once Benigni won an upset at the SAG Awards and brought his traveling circus to awards audiences desperate for a) fun, and b) a narrative, it was all over. Look at Helen Hunt’s eyes when she announced the winner! She knows what’s coming, and she’s terrified.

Where to stream Life Is Beautiful

Year: 2000
Category: Best Picture
Who Should’ve Won? Crouching Tiger, Hidden Dragon

Nobody tell Colin Jost — or Elizabeth Taylor, really — but Gladiator is a fine action movie with Ridley Scott pretensions of waving wheat fields and featuring a ferocious lead performance from Russell Crowe, but it is a far cry from Best Picture in any year, but especially in a year when it was up against Crouching Tiger, Hidden Dragon, Traffic, and future cable-TV champion Erin Brockovich. Sorry, but that is fully insane. Sideways middle thumb to this one!

Where to stream Gladiator

Year: 2001
Category: Best Picture
What Should’ve Won? The Lord of the Rings: The Fellowship of the Ring

This one might be controversial, because A Beautiful Mind has its fans, but those people are WRONG! It is a terrible movie! This isn’t kneejerk anti-Ron Howard snobbery either. Howard has made a lot of very good movies. He should’ve won in 1995 for Apollo 13! (See above Braveheart rant.) But A Beautiful Mind is over-sentimentalized, schmaltzy, faux-intelligent garbage, and we should all get onboard with that. Yes, The Lord of the Rings finally had its moment in the sun in 2003, but it should have already been an Oscar winner for its first (and best) installment.

Where to stream A Beautiful Mind

Year: 2012
Category: Best Supporting Actor
Who Should’ve Won? Philip Seymour Hoffman, The Master

The thing about the 2012 Supporting Actor race is that all five of the nominees had previously won Oscars, which had never happened in an acting category before. This fact was trumpeted a lot, most irritatingly in that year’s nomination announcements, which was the year that Seth Macfarlane and Emma Stone did a whole annoying song and dance before announcing each set of nominees, and for this one, they spoiled the whole category right at the beginning by calling out each nominee as a former winner. We’re not stupid! We know if you start calling out Alan Arkin as a former Oscar winner, then all the other nominees are gonna be Oscar winners, because nobody wants to make (pre-Revenant) Leo DiCaprio feel bad! Idiots.

Anyway, the hell of it is, with five former winners, no single one of them had all that much momentum to win a second (or, in the case of Silver Linings Playbook‘s Robert De Niro, a third), so the Academy just kind of shrugged and gave it to Waltz for delivering the exact same performance he gave in Inglourious Basterds. Meanwhile, despite the fact that Philip Seymour Hoffman was a lead actor slumming it in Supporting, he still gave one of the year’s best performances, and, as it sadly turned out, this was Oscar’s last chance to award him.

Where to stream Django Unchained

Year: 2011
Category: Best Actress
Who Should’ve Won? Viola Davis for The Help

This one was not easy! Meryl Streep is our greatest acting talent, and she deserves to have three Academy Awards to her name. But they chose to give it to her for The Iron Lady, one of her least essential performances in one of her least essential movies, and one that, frankly, makes her look less than what she is. This is Meryl Streep! She’s more than just some Academy-friendly parlor trick where some canny makeup and a wig makes her resemble a historical figure. That is for lesser actors! Meryl could have and should have won her third Oscar for any number of performances, from Adaptation to The Devil Wears Prada to Julie & Julia. And that’s only counting the ones she was nominated for! (Justice for her Clarissa Vaughan in The Hours!)

The balm on this bullshit win is that a) Meryl gave one of the best Oscar acceptance speeches in the modern era, both gracious and memorable and a little funny, and b) Viola Davis ended up winning her Oscar for a better movie, so now when we think of Viola Davis’s Oscar, we don’t have to think “Emma Stone white-savior movie.” Which is nice.

Where to stream The Iron Lady