If history is any indication, it's unlikely that Sunday's Academy Awards ceremony will end with the most deserving nominee going home with the "best picture" Oscar. This is common sense for anyone who cares about cinema and has been paying attention in recent years. How did The Artist beat out The Tree of Life in 2011? How did Argo beat out Zero Dark Thirty in 2012? How did Birdman beat out Boyhood in 2014? When will Hollywood stop its self-congratulatory streak of crowning showy movies simply because they are meta commentaries about show business? (A trend that looks like it will continue with La La Land.)
The iffy track record of the Academy is nothing new. One only has to look at a list of all the past best picture winners to see how poorly many of them have aged compared with the films they beat out. According to my own survey of the best picture winners from the last 50 years, only 40% of the time (or 20 of the last 50 best picture Oscar winners) did the best film win of those that were nominated. Note that this number would be far less if compared to all the films of any given year. Quite often the year's best films aren't even nominated (like this year: Silence). Of the 20 best picture winners that I think Oscar got right given the nominated choices, I think only about six can truly lay claim to being the overall best film of their year. These would be The Godfather, Annie Hall, The Silence of the Lambs, Unforgiven, Schindler's List, and No Country for Old Men.
Many of the best picture winners over the years are now mostly forgotten, or widely panned (ahem, Crash). The reasons for Academy misfires are complex. The most important reason is probably that a film's greatness is often determined by how well it stands up over time, which is obviously impossible to determine just a few months after it comes out. The Oscars are more about marketing and momentum and the current zeitgeist than they are about real assessment of quality. It's a wonder the best picture Oscar winner has ever hit the bullseye.
So which nominated film each year was most deserving? Here's my take on where the Academy got it right, and where the Academy would probably want a do-over, from the last 50 years:
1966 Winner: A Man for All Seasons Nominated film that should have won: A Man for All Seasons
1967 Winner: In the Heat of the Night Nominated film that should have won: The Graduate
1968 Winner: Oliver! Nominated film that should have won: Romeo and Juliet
1969 Winner: Midnight Cowboy Nominated film that should have won: Butch Cassidy and the Sundance Kid
1970 Winner: Patton Nominated film that should have won: Five Easy Pieces
1971 Winner: The French Connection Nominated film that should have won: A Clockwork Orange or The Last Picture Show
1972 Winner: The Godfather Nominated film that should have won: The Godfather
1973 Winner: The Sting Nominated film that should have won: The Exorcist
1974 Winner: The Godfather Part II Nominated film that should have won: Chinatown
1975 Winner: One Flew Over the Cuckoo's Nest Nominated film that should have won: One Flew Over the Cuckoo's Nest
1976 Winner: Rocky Nominated film that should have won: Taxi Driver
1977 Winner: Annie Hall Nominated film that should have won: Annie Hall
1978 Winner: The Deer Hunter Nominated film that should have won: The Deer Hunter
1979 Winner: Kramer vs. Kramer Nominated film that should have won: Apocalypse Now
1980 Winner: Ordinary People Nominated film that should have won: Raging Bull
1981 Winner: Chariots of Fire Nominated film that should have won: Chariots of Fire
1982 Winner: Gandhi Nominated film that should have won: E.T.
1983 Winner: Terms of Endearment Nominated film that should have won: Tender Mercies
1984 Winner: Amadeus Nominated film that should have won: Amadeus
1985 Winner: Out of Africa Nominated film that should have won: Out of Africa
1986 Winner: Platoon Nominated film that should have won: The Mission
1987 Winner: The Last Emperor Nominated film that should have won: The Last Emperor
1988 Winner: Rain Man Nominated film that should have won: Rain Man
1989 Winner: Driving Miss Daisy Nominated film that should have won: Dead Poet's Society
1990 Winner: Dances with Wolves Nominated film that should have won: Goodfellas
1991 Winner: The Silence of the Lambs Nominated film that should have won: The Silence of the Lambs
1992 Winner: Unforgiven Nominated film that should have won: Unforgiven
1993 Winner: Schindler's List Nominated film that should have won: Schindler's List
1994 Winner: Forrest Gump Nominated film that should have won: The Shawshank Redemption
1995 Winner: Braveheart Nominated film that should have won: Braveheart
1996 Winner: The English Patient Nominated film that should have won: Fargo
1997 Winner: Titanic Nominated film that should have won: Good Will Hunting
1998 Winner: Shakespeare in Love Nominated film that should have won: The Thin Red Line
1999 Winner: American Beauty Nominated film that should have won: The Sixth Sense
2000 Winner: Gladiator Nominated film that should have won: Gladiator
2001 Winner: A Beautiful Mind Nominated film that should have won: The Lord of the Rings: The Fellowship of the Ring
2002 Winner: Chicago Nominated film that should have won: The Pianist or Gangs of New York
2003 Winner: The Lord of the Rings: The Return of the King Nominated film that should have won: Lost in Translation
2004 Winner: Million Dollar Baby Nominated film that should have won: Sideways
2005 Winner: Crash Nominated film that should have won: Capote or Munich
2006 Winner: The Departed Nominated film that should have won: The Departed
2007 Winner: No Country for Old Men Nominated film that should have won: No Country for Old Men
2008 Winner: Slumdog Millionaire Nominated film that should have won: Slumdog Millionaire
2009 Winner: The Hurt Locker Nominated film that should have won: Inglourious Basterds
2010 Winner: The King's Speech Nominated film that should have won: The Social Network
2011 Winner: The Artist Nominated film that should have won: The Tree of Life
2012 Winner: Argo Nominated film that should have won: Zero Dark Thirty
2013 Winner: 12 Years a Slave Nominated film that should have won: 12 Years a Slave
2014 Winner: Birdman Nominated film that should have won: Boyhood
2015 Winner: Spotlight Nominated film that should have won: Spotlight