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Biggest Oscar Mistakes: Us Weekly’s Film Critic Reflects on the Movies That Should Have Won Best Picture

Oscar mistakes and films who should have won.
Jesse Eisenberg in "The Social Network"

2010 Best Picture winner: The King’s Speech 

Shoulda-been: The Social Network

Yeesh. It’s only been two years, and the King’s Speech coronation already ranks as an infamous Oscar goof. Though there’s admittedly something inspiring and charming about the story of King George’s true-life struggle to overcome his stutter and rule England, it lacks the sizzle of Mark Zuckerberg’s true-life struggle to overcome lawyers, broken friendships and the Winklevoss twins and rule social media. With the killer one-two punch of Aaron Sorkin’s searing screenplay and David Fincher’s crisp direction, the drama mesmerizes from the moment Jesse Eisenberg (as Zuckerberg) and Rooney Mara verbally spar it out in a college bar. (Ahem, before the opening credits). All 900,000,000-and-counting Facebook users should have demanded a recount via their status updates. (Hey, it’s better than looking at someone else’s vacation photos!)

Brokeback Mountain
Jake Gyllenhaal and Heath Ledger in “Brokeback Mountain”

2005 Best Picture winner: Crash 

Shoulda-been: Brokeback Mountain

And now, a moment of silence for the timeless, heart-piercing Western that should have taken a ride into glory. . . then got robbed by a disjointed we-are-all-connected drama. Jake Gyllenhaal and Heath Ledger pour their souls into their roles as sturdy cowboys who forge a doomed 20-year relationship with each other. (Anne Hathaway and Michelle Williams, as their respective suspicious spouses, also shine in their first grown-up performances). The haunting, cliché-free love story between two men is told in few words but speaks volumes in terms of its relevancy in American cinema. The buzz on Crash, meanwhile, went silent sometime around 2006.

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Saving Private Ryan
Tom Hanks in “Saving Private Ryan”

1998 Best Picture winner: Shakespeare in Love

Shoulda-been: Saving Private Ryan 

Steven Spielberg is the most successful director of our era and on the cusp of taking home a third best director Oscar (for Lincoln), so let’s not get in the business of feeling sorry for him. Still. It’s truly baffling that a frothy, meandering comedy — even one that stars a glowing, pre-GOOP Gwyneth Paltrow — beat out his brilliant and captivating World War II masterpiece. (Want proof? Go to Youtube and take a gander at the visibly crestfallen look on presenter Harrison Ford’s face when he opens the envelope.) In the story of a military unit’s quest to locate a young soldier (Matt Damon) and send him home, Spielberg captures war at its most harrowing and achingly tragic. He even managed to squeeze a gritty performance out of Vin Diesel.     

Jerry Maguire
Tom Cruise and Jonathan Lipnicki in “Jerry Maguire”

1996 Best Picture winner: The English Patient 

Shoulda-been: Jerry Maguire

Do you know that the human head weighs 8 pounds? Do you know that bees and dogs can smell fear? And can you friggin’ believe that Cameron Crowe’s sparkling and emotionally textured gem was overlooked in favor of a long-winded and pretentious World War II romance? (Actually, given the Academy’s reluctance to reward contemporary feel-gooders, it is believable). Tom Cruise — in only his most open and engaging performance ever — is the smooth sports agent; Cuba Gooding Jr. is his hot-rod NFL star client; Renee Zellweger is the single mom who completes him. Between its biting sports elements and straight-from-the-heart romance, this movie continues to entertain with each passing viewing. Good thing it airs on cable every five minutes.

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Toy Story
Toy Story

1995 Best Picture winner: Braveheart

Shoulda-been: Toy Story

The Pixar movie that started it all should have won out just for its groundbreaking computer animation alone. Factor in its wildly imaginative narrative — bedroom toys come alive! — and cue the Titanic-like shoo-in. But nooooo. . . . it wasn’t even nominated. How fantastic is this plastic? It ushered in two fully rounded, iconic characters, cowboy Woody (voice of Tom Hanks) and astronaut Buzz Lightyear (voice of Tim Allen), and turned Mr. Potato Head into a salty comic. Two sequels and gazillions of DVD sales later, this clever comedy still delivers joy to kids of all ages (and makes for a cheap babysitter). Or pop in Mel Gibson’s heavy-handed, ultra-bloody take on 14th century Scottish patriot William Wallace. Your choice.    

Do The Right Thing
Spike Lee in “Do The Right Thing”

1989 Best Picture winner: Driving Miss Daisy

Shoulda-been: Do the Right Thing

Hey, want to rile up Spike Lee? Tell him that the New York Knicks are overrated and remind him that his thought-provoking classic  — with a pulse that still beats to this day — didn’t even make the Best Picture short list. Lee, who wrote, directed and stars, set his film on the hottest day of the year in racially divided Brooklyn. As the temperature rises, so do the tempers between an Italian pizza parlor owner (Danny Aiello) and his African-American customers (which, FYI, includes notorious Breaking Bad alum, Giancarlo Esposito). Controversial and provocative with a thumping Public Enemy soundtrack, the film refuses to present any easy answers with its unsettling resolution. Yet, the Academy resolved to give its big award to a significantly more conventional drama about race relations and a persnickety Southern woman and her loyal driver’s trips to the Piggly Wiggly. Fight the power, indeed.

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