I frequently wish that a better movie had won the Best Picture statuette. Some years there isn't a better movie, or maybe the better movie was foreign and no one saw it or it didn't qualify. But some years, the Academy just screws up.
1938 - You Can't Take It with You
Now, I'm not saying this is a bad movie - far from it. It's a pleasant, uplifting bit of Capra-corn. But I do object to this win because the competition was so obscenely better. Two great crowd-pleasers, The Adventures of Robin Hood and Pygmalion, were nominated and so was Grand Illusion, a.k.a. one of the single greatest movies ever made. Since Grand Illusion was a foreign film, it was always a long-shot. But really, Academy - you chose a fluffy movie with some quirky characters over a ground-breaking masterpiece that examined class and anti-semitism among World War I soldiers.
1941 - How Green Was My Valley
John Ford's exercise in old country whimsy and tasteful tragedies completely misses the point of his source material. Richard Llewellyn's masterpiece about Welsh miners is extremely bleak and could really be deemed anti-nostalgic; the movie cuts out anything that can't be made to have a silvery lining or to compel cathartic tears with a background of choral music. Plus, Citizen Kane lost.
1944 - Going My Way
The fact that this shlock was even nominated is objectionable. In a year when Double Indemnity or Gaslight could have won, the Academy chose a comedy with Bing Crosby as a singing priest. This movie is so wholesome it should make toddlers gag - and this is coming from someone who cries during Little Women every time I watch it (frequently). This isn't not as good as the competition; it's just plain bad.
1952 - The Greatest Show on Earth
Without a doubt, the worst movie to ever win the Best Picture statuette, this bloated, boring melodrama set in a circus and starring Charlton Heston inexplicably made a lot of money, but certainly hasn't held up over time. It's also worth pointing out that Singin' in the Rain was not even nominated. This was really a lifetime achievement award for Cecil B. DeMille in disguise, but even so, it was the golden age of Hollywood and there were at least a dozen films that should have won over this.
1956 - Around the World in Eighty Days
I will admit that this movie is entertaining except when you're cringing over the racism and happy-go-lucky embrace of British imperialism. It was also a year of obscenely long movies with massive casts, so this one fit right in. What's frustrating is its lack of substance. It's just a silly movie with tons of famous people in it and scenes of not so authentic foreign cultures. Even The King and I, irritating as it is, was made with a minimal engagement with the realities of racism and imperialism.
1965 - The Sound of Music
I really loathe this movie. Christopher Plummer has apparently referred to this film as "The Sound of Mucus" and I completely agree. Lots of excellent musicals were made in the 60's and this was not one of them. The songs are so annoying that they could be used in lieu of water-boarding. Yuck.
1980 - Ordinary People
I'm not entirely sure why this movie makes me so nauseated, but it might have something to do with the endless repetition of Pachelbel's Canon or the therapist who apparently has no other patients but Timothy Hutton. There was stiff competition this year from Raging Bull, but most of my objection comes from a deep-seated dislike of this movie. Or Pachelbel's Canon.
1997 - Titanic
If any other movie had won in 1997, I wouldn't care. But this particular choice proved once and for all that the Oscars are a popularity contest. Yes, it made an insane amount of money. Yes, the special effects were fancy. The acting could have been worse, but there are three main reasons why this movie is awful: 1) The script was a daytime soap opera rewritten to be aimed at semi-rebellious teenage girls; 2) It posits that independent women prove their independence by learning how to spit; and 3) Celine Dion sings. And she sings the soapiest, sappiest song of all time.
2002 - Chicago
Everyone got really excited about this movie when it came out because it was the first major musical to come out of Hollywood in several decades. Perhaps it was the lack of other musicals for comparison that led people to believe that Renee Zellweger, Richard Gere, and Catherine Zeta Jones could sing and dance - they can't. The only actual singer in the cast was Queen Latifah and she was the only one who belonged there. Musicals cast with actors who can't sing or dance should not win Oscars.
2011 - The Artist
I feel a little bad for including this on the list, but I have to. I think it's great that so many Americans were willing to sit down and watch a foreign film. Except that that's totally cheating because this film is "silent" and thus does not require subtitles. Granted, it was a really disappointing year - nearly all the nominees were politically correct to the nth degree - but still, it's kind of terrible that the only foreign films that ever win this award are in English or silent.