-- Nancy Witcher Astor
Lost To: Forrest Gump
I have a healthy respect for Quentin Tarantino's work, but I daresay I don't place him on the pedestal most of the internet does. That said, I can still recognize Pulp Fiction's importance to filmmaking in general. Tarantino typically challenges traditional Hollywood conventions, but arguably never more effectively than with his breakout movie. Jump cuts, dialogue, casting, narrative flow, none of it is traditional and all of it works. The fact that it lost to Forrest Gump isn't a complete travesty, but is inching that way as the years go by. Film Studies students aren't writing dissertations on the Bubba Gump Shrimp Co. after all...
Lost To: Rocky
The Golden Age of Robert De Niro makes it a shame that this generation probably knows him as the dad in the Meet the Parents when he'd entered his "just cash the paycheck" phase instead of from his Taxi Driver, Deer Hunter, Raging Bull days. I don't have enough faith in today's moviegoing audience to think that an Oscar win for Taxi Driver would mean it was more well known today, but it couldn't hurt. Rocky was a perfectly fine movie, but it didn't have nearly as much to say to society as Taxi Driver.
Lost To: The English Patient
This one keeps getting worse as the years go by. Fargo lost at the time for its rather brutal nature that would arrive in spurts without being announced. Since then, as audiences have become more accepting of that sort of story-telling, Fargo's brilliance has become somewhat undisputed. Meanwhile, The English Patient is another boring romance, this one adapted poorly from a book, removing any depth or political commentary from the story, leaving only Ralph Fiennes to flounder in a romantic lead role and an uninspiring script to work with. The Coens arguably got their makeup call with the example listed in the intro.
Lost To: Dances With Wolves
Seeming like a worthy winner at the time, Dances With Wolves spawned a bit of a trend in Hollywood. Unfortunately for it, its imitators actually laid-bare its own flaws. The string of "white guy shows up to save the problems of a different ethnicity" movies along with Kevin Costner's later works revealed this movie's arrogance. Since Costner loves to martyr himself, I like to think the subsequent backlash to the movie is actually more satisfying to him than the Academy Award. Anyway, on the other hand, you had Goodfellas: the movie that probably ended De Niro's run of caring about every one of his roles (if it didn't end here, it ended with Casino, but I would argue that was after he could only care in short bursts), it's thought to be one of the best gangster movies of all time.
Lost To: Kramer vs. Kramer
I will admit to having never seen Kramer vs. Kramer, and yet this is still obviously a travesty. Apocalypse Now has remained culturally relevant for 3 decades, while Kramer vs. Kramer sounds like a particularly high-concept spin-off of "Seinfeld". Books have been written about Apocalypse Now's troubled shoot, and how much or how little of Marlon Brando's performance was true acting vs. how much was due to the conditions, but nevertheless, a masterpiece emerged. "I love the smell of napalm in the morning" is one of the most enduring quotes of a movie probably has decades more of societal relevance left in it.
Lost To: Chicago
A tour de force from beginning to end, Gangs of New York managed to make John C. Reilly seem like a legitimate actor instead of someone who subsists on whatever scraps Will Ferrell feeds him. Chicago managed to also include him. Gangs of New York featured the impressive ranges of Leonardo DiCaprio and Daniel Day-Lewis. Chicago featured Renée Zellweger trying to squint the audience to death. Where Gangs of New York featured amazing filmmaking, Chicago featured songs. This could have easily been higher on the list if only Cameron Diaz hadn't featured so prominently and hurt my case.
Lost To: The Lord of the Rings: The Return of the King
The LotR win here is a perfect example of a cumulative win. The LotR movies had been the second best two years running (losing to A Beautiful Mind correctly in 2001 and Chicago in 2002... they really screwed up 2002), and the Academy realized they wouldn't get another shot to recognize their greatness. The collateral damage was one of Sean Penn's greatest movies going unrecognized (though Penn himself would win the Best Actor). This movie announced to the world that Clint Eastwood was more than a competent director, he could be a transcendent one.
Lost To: Million Dollar Baby
You could argue that Million Dollar Baby's win was a "makeup call" for Clint Eastwood's Mystic River and you wouldn't get much disagreement from me. It's a perfect example of the Academy's agendas just creating more problems for them. They had to later pay back both Scorsese (for Best Director) and are still waiting to make good with DiCaprio (for Best Actor). They lucked out two years later when Scorsese was the easy winner from a weak year, but DiCaprio hasn't had quite as clear-cut of an easy choice yet. A biopic of an American historical figure losing to a paint-by-numbers drama? Unheard of these days.
Lost To: Shakespeare In Love
The definitive war movie for a generation, this has to be one the Academy is embarrassed to look back on. This is probably the one on the list that everyone just assumes won and would be shocked to hear it didn't. They gave the Oscar to a movie with Gwyneth Paltrow; a massive inside-joke referencing Shakespeare's own works while telling a fictitious story about his life. Quick, tell me one scene you remember from it. Compare that to Saving Private Ryan and the impact it had. Best Picture is supposed to be all-encompassing. In the pure subjectivity of an awards show, Best Picture is admittedly the most subjective of all, and in this case, the sheer cultural significance of SPR should have pushed it over the top.
Lost To*: Oliver!
Ignore for the moment that it commits the cardinal sin of setting itself in the too-near future (although since it's based on a book, it can hardly be blamed for that) and it's an amazing, ahead of its time sci-fi adventure. That description doesn't do it justice, so I'll just say that it holds a 97% on Rotten Tomatoes and was selected by the Library of Congress for preservation for being "culturally, historically, or aesthetically" significant. It lost to a musical version of Oliver Twist. I'll just let that sink in for a minute. And oh, as a parting shot, it wasn't even nominated. That's right: the film widely regarded to be among the best of all time couldn't crack the Academy's Top 5 for 1968.
*Can you lose a race you never ran?
Lost To: Slumdog Millionaire
Another one that wasn't even nominated, the outrage over its exclusion was a major reason the Academy expanded to 10 nominees the following year. Only having 5 nominees for 2008 doesn't excuse them, however, as The Reader is the easy-to-spot weak entry on the list that should've been replaced by TDK. I'm not arguing it should've won the Oscar (Slumdog Millionaire was more than worthy), but it's lack of a nomination is quite the snub in and of itself.