Well, time has been flying and now we’re a third of the way done with What Should’ve Won That Could’ve Won, at 33 movies in! I thought we should take a moment to look back on the project so far. I also wanted to check in to make sure people are out there reading the series, because nobody comments on blogs anymore. If you’re out there, are you enjoying the series? Anyone still around from when the series began back in 2012 and surprised to see it start up again? Are there any picks that infuriated you that you’re still smarting about? How about the ads, are they funny and worth doing? If you’re reading these, please post a comment below to say hi!
And if you’re new to the blog, welcome! This is a series called What Should’ve Won That Could’ve Won where I declare which movie should have won the Oscar for Best Picture for each of the Academy’s first 100 years. Below, you can click on each line and link to a post where I go through each movie and explain what the nominees were, how hard my decision was, who made the movie, what the story is, whether my pick got any nominations or wins, why it didn’t win (if it lost), and, finally, 4-6 reasons why is should’ve won (or did win).
- 1928: What Did Win: Wings, What Should’ve Won: The Crowd
- 1929: What Did Win: Broadway Melody of 1929, What Should’ve Won: Applause
- 1930: What Should’ve Won and Did Win: All Quiet on the Western Front
- 1931: What Did Win: Cimarron, What Should’ve Won: City Lights
- 1932: What Should’ve Won and Did Win: Grand Hotel
- 1933: What Did Win: Cavalcade, What Should’ve Won: I Am a Fugitive From a Chain Gang
- 1934: What Should’ve Won and Did Win: It Happened One Night
- 1935: What Should’ve Won and Did Win: Mutiny on the Bounty
- 1936: What Did Win: The Great Ziegfeld, What Should’ve Won: Modern Times
- 1937: What Did Win: The Life of Emile Zola, What Should’ve Won: The Awful Truth
- 1938: What Did Win: You Can’t Take It With You, What Should’ve Won: Holiday
- 1939: What Did Win: Gone with the Wind, What Should’ve Won: The Wizard of Oz
- 1940: What Should Have Won and Did Win: Rebecca
- 1941: What Did Win: How Green Was My Valley, What Should’ve Won: Citizen Kane
- 1942: What Did Win: Mrs. Miniver, What Should’ve Won: To Be Or Not to Be
- 1943: What Should’ve Won and Did Win: Casablanca
- 1944: What Did Win: Going My Way, What Should’ve Won: Double Indemnity
- 1945: What Did Win: The Lost Weekend, What Should’ve Won: Scarlet Street
- 1946: What Did Win: The Best Years of Our Lives, What Should’ve Won: It’s a Wonderful Life
- 1947: What Did Win: Gentlemen’s Agreement, What Should’ve Won: Black Narcissus
- 1948: What Did Win: Hamlet, What Should’ve Won: Fort Apache
- 1949: What Did Win: All the King’s Men, What Should’ve Won: The Third Man
- 1950: What Did Win: All About Eve, What Should’ve Won: Sunset Boulevard
- 1951: What Did Win: An American in Paris, What Should’ve Won: A Place in the Sun
- 1952: What Did Win: The Greatest Show on Earth, What Should’ve Won: High Noon
- 1953: What Did Win: From Here to Eternity, What Should’ve Won: Roman Holiday
- 1954: What Did Win: On the Waterfront, What Should’ve Won: Rear Window
- 1955: What Should’ve Won and Did Win: Marty
- 1956: What Did Win: Around the World in 80 Days, What Should’ve Won: The Court Jester
- 1957: What Did Win: The Bridge on the River Kwai, What Should’ve Won: 12 Angry Men
- 1958: What Did Win: Gigi, What Should’ve Won: Vertigo
- 1959: What Did Win: Ben-Hur, What Should’ve Won: Some Like It Hot
- 1960: What Should’ve Won and Did Win: The Apartment

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