Oscars: Top Best Oscar Winners Of All-Time Ranking

There have now been 90 years of Oscar winners and losers and, along with them, 90 years of cheers for deserving victors as well as 90 years of jeers for imposters that snuck into the winner’s circle. Some best picture winners still retain their status as all-time classics that people today still watch and love — Casablanca, All About Eve, Lawrence of Arabia, the two Godfathers, among others — while there are those that either haven’t been seen by anyone in decades (for good reason) — Cimarron, Cavalcade, The Great Ziegfeld, The Greatest Show on Earth, Around the World in 80 Days — or are almost instantly perceived through the next morning’s hangover as “What were they thinking?” choices, including such toe-stubbers as Oliver!, Driving Miss Daisy, Chicago and Crash.

I’ve been watching the annual spectacle since I was nine years old and have more often come away disappointed (and sometimes royally pissed off) by the winners than satisfied. Sometimes the Academy has gone through periods of preferring “entertainments” over deep-dish dramas, while at others the show has simply felt like insiders patting fellow members of the Hollywood club on the back. There have been sympathy votes for ailing artists and comeback kids, prizes for people who should have won the year before and get make-up trophies instead. And sometimes Hollywood wants to demonstrate that it’s “grown up” and does so by embracing serious, small and/or socially conscious films, sometimes misguidedly so; we’re in one of those periods right now. And then there have been years when everyone was just out to lunch.

I’ve seen all the winners, from 1927-28, when William Wellman’s robustly entertaining World War I flying drama Wings won the award for “production” and F. W Murnau’s visually sublime Sunrise took a parallel award for “artistic quality of production,” to Barry Jenkins’ most recently victorious Moonlight, one of the smallest-scale and most atypical best picture winners in awards annals.

Following are my ten favorite all-time best picture Oscar winners — none, I’m only mildly surprised to say, have been made in the last 24 years. They are listed chronologically.

I’m not including Sunrise here because Wings has almost always been considered the actual best picture winner, with the “arty” (and very influential) Sunrise having been relegated to a special category that was abandoned after the Academy Awards’ first year. The 1930s was one of the greatest decades for Hollywood moviemaking and many films from that period rank as all-time favorites. Unfortunately, the Academy did a very good job of ignoring Hollywood’s best creations from the first full decade of sound pictures, honoring instead “distinguished” literary adaptations and biopics instead of snappy romantic comedies and deep-dish melodramas. Therefore, there are no 1930s Oscar winners on my all-time list because the best films from that decade were very rarely even nominated.

For the list of my ten least favorite all-time best picture Oscar winners, click here.