#10. Chinatown (1974)
Lost to: The Godfather Part II
Well, no one will argue that it should have won, but still. Roman Polanski’s film made a true leading man out of Jack Nicholson. It grabbed eleven nominations, only taking home one. That being said, that one was for Original Screenplay, written by Robert Towne, which may be the greatest even written. Entire courses could be taught on this screenplay alone and Polanski and his actors delivered a perfect translation of it to the screen. Also starring Faye Dunaway and the great John Huston, the story of power and corruption still stands as one of the greatest films of the 1970’s (or any decade for that matter). It’s just a shame it ran into the greatest movie sequel of all time.
#9. Cabaret (1972)
Lost to: The Godfather
Seems weird, doesn’t it? Well, the Liza Minnelli vehicle is on this list for one important reason: it won the most Oscars of all time without taking home the big one. Cabaret grabbed ten nominations and won eight of them, including Best Actress for Minnelli, Best Supporting Actor for Joel Grey, and Best Director for Bob Fosse. In most other years, it may have walked away with Best Picture, but it was up against quite possibly the greatest American film ever made. It had a great pedigree – Fosse directed the Broadway version of “Chicago” and brought his songwriters with him for Cabaret. But Francis Ford Coppola’s masterpiece was too much to overcome.
#8. Brokeback Mountain (2005)
Lost to: Crash
I’ll go on record right now and say that I am not as big a fan of this film as most people. That being said, the divide between critics and the Academy was never so visible than it was in 2005, when the Oscar went to a hyperlink film about race relations in Los Angeles instead of a groundbreaking film about gay cowboys. Ang Lee’s “Brokeback Mountain” was a force to be reckoned with – critics loved it and it broke barriers in terms of a mainstream film taking a look at such a touchy subject. It gave the world a collection of young stars – Heath Ledger, Jake Gyllenhaal, Anne Hathaway, Michelle Williams – that would become the future of the industry. But, in the end, the topic may have been a little too risque and the award went to the much more audience friendly film packed full of A-list stars. The late Ledger’s role as The Joker may be his defining performance, but his work here as Ennis is uncompromisingly subtle and complicated.
#7. Jaws (1975)
Lost to: One Flew Over the Cuckoo’s Nest
The summer blockbuster didn’t really exist until 1975, when a young filmmaker named Steven Spielberg unleashed a shark upon the world. “Jaws” didn’t get as much Oscar love as you would think – only four nominations and three wins (Film Editing, Original Score, Sound), but the lack of recognition for Spielberg in the directing category was a surprise and would begin a strange trend for his films. Eight Spielberg films have been nominated for Best Picture – only one has won (Schindler’s List). Spielberg himself has only won two Best Director Oscars, for “Schindler’s List” and “Saving Private Ryan.” It’s just another example of a director viewed by most as one of the greatest of all time, but without the hardware to back it up. If you’re asking me, while “Jaws” may not have “deserved” the Oscar in 1975 (Milos Forman’s adaptation of Ken Kesey’s novel is a brilliant film), it’s still his best film.
#6. The Wizard of Oz (1939)
Lost to: Gone with the Wind
We already talked about one other loser from 1939 (“Mr. Smith Goes to Washington”), but it pales in comparison to this mammoth of a film. While Frank Capra’s story of a greater America is inspiring, it will never match the impact this classic film made on the world. “The Wizard of Oz” was nominated for six Oscars, winning two (Original Score, Original Song), somehow missing out on any technical awards (though, to be fair, they were in their infancy at the time). Director Victor Fleming shapes a dream-like story of a young girl’s trip to Oz – a magical world with a tin man, a scarecrow, and a lion all searching for the one thing they believe will complete them each. The three of them and Dorothy (Judy Garland) journey along the yellow brick road to meet the wizard and escape the Wicked Witch of the West, accompanied by Toto the dog. It’s great family fun and has since been only expanded in its mythology. But, let’s be honest. Nothing was going to beat “Gone with the Wind.”
#5. Saving Private Ryan (1998)
Lost to: Shakespeare in Love
Steven Spielberg’s highest rated film on the list may not be his best, but it was the most unexpected loser, for sure. From “Saving Private Ryan’s” premiere, it was exalted for its realism, honesty, and true depiction of warfare, specifically the scenes on the beaches of Normandy. Nominated for eleven Oscars and taking home five (including Best Director), the war epic still suffered from some of the typical Spielberg tropes (the final act is a bit melodramatic, for sure). It was chosen as the front-runner early on, but, in the end, the Academy chose a lighthearted comedy named “Shakespeare in Love,” about the young playwright’s love affair. It was early proof that the Weinsteins (Miramax) were a lobbying force to be reckoned with, pushing their little love story to Best Picture (and a Best Actress award for Gwyneth Paltrow).
#4. Citizen Kane (1941)
Lost to: How Green Was My Valley
It’s widely identified as the greatest American film of all time. It was a labor of love and obsession by one of the industry’s greatest directors at such a young age. It was a cutting attack on the newspaper industry veiled as a fictional biopic. But, while 99% of film enthusiasts may look at this as one of the biggest travesties of all time, this was never unexpected. “Citizen Kane” has aged more gracefully than any film. As time has gone on, the respect and admiration for what Orson Welles created has grown and blossomed. But, in 1941, John Ford’s “How Green Was My Valley” taking home the top prize was not a surprise. It didn’t incite riots. No one set the theater ablaze out of anger and frustration. It was just early proof that, regardless of how much weight we put on the Oscars, they mean nothing when debating what films are truly “great.”
#3. Raging Bull (1980)
Lost to: Ordinary People
We’ve seen what felt like the Oscars vs. Steven Spielberg saga in a few places on this list, but a much larger, more obvious battle was a longstanding divide between the Academy and the great Martin Scorsese. Beginning in 1976 with “Taxi Driver,” Scorsese had four films nominated for Best Picture before finally winning in 2006 with “The Departed,” though he made plenty of other Oscar-worthy films during that span. This film was the second of those losers, but the first that was the overwhelming favorite. Raging Bull was a tour-de-force for Robert De Niro and one of the most intense, honest films that revolved around a sport of all time. But it was exceedingly dark and painful to watch as Jake LaMotta’s downward spiral was captured fully by Scorses and Michael Chapman’s black and white cinematography. “Raging Bull” grabbed eight nominations, only winning two (Best Actor, Best Film Editing). But, its loss to Robert Redford’s family drama “Ordinary People” has gone down as one of the biggest surprises (and disappointments) in Oscar history.
#2. Goodfellas (1990)
Lost to: Dances with Wolves
Martin Scorsese had already been “cheated” by the Academy once, with the previous entry on this list. Ten years later, he collaborated with author Nicholas Pileggi to adapt his novel Wiseguys into the motion picture that would become “Goodfellas.” Starring Ray Liotta, Joe Pesci, Robert De Niro, Paul Sorvino, and Lorraine Bracco, the true life mob story of a gangster-turned-informant portrayed protagonist Henry Hill as a kid looking for an opportunity to “be someone” in a world that was defined by this set of criminals. Eventually, his entry into that world slowly destroys him and the people he loves, forcing him to turn his back on a life he would still go back to in a heartbeat. Nominated for six Oscars (winning just one – Best Supporting Actor for Pesci), “Goodfellas” has long been regarded as one of the biggest Oscar misses of all time. Kevin Costner’s sweeping, yawn-inducing western “Dances with Wolves” took home the gold (along with six other wins and twelve total nominations). Liotta was never better, De Niro found a new place in cinema, and Pesci gave a juggernaut of a performance in, ironically, the same year he would be bested by a pre-teen (“Home Alone”). “Goodfellas” took a mob story, made it a personal character study, and only sits behind The Godfather, Parts I and II in the pantheon of gangster films. Which is ironic, because it was also nominated against “The Godfather Part III,” an awful, awful film. “Goodfellas” may not be Scorsese’s best film, but it damn sure should have a Best Picture Oscar.
#1. Star Wars (1977)
Lost to: Annie Hall
And so it comes to this. Sometimes, a film defines a genre. Sometimes it defines a fan base. Other times, it defines an entire movement of culture. In 1977, George Lucas crafted this first film in a trilogy that would essentially change the world. Star Wars was something different: a western set in space. The Lucas formula used interesting characters and an expanded mythology to create what felt more like a comic book issue for the silver screen. It grabbed ten total nominations, winning six (all in technical or music categories). It lost out on the big prize, Best Director, Supporting Actor (Alec Guinness), and Original Screenplay. It wasn’t a huge surprise – the Academy wasn’t quite at the stage to truly accept a genre film. Fast forward to 2013. Now Disney owns the rights to make more Star Wars films, after George Lucas finally phased himself out, before he could destroy his creation further. Regardless of what happens from now on, the original trilogy and, more specifically, the film that kicked it off, holds a place in society as one of the most important cultural events of the last fifty years. Should it have won? Not sure. “Annie Hall” is a really good movie.
— Joshua Gaul