Rank 'Em: The Best Picture Winners of the '60s

Decade by decade, I'm ranking the winners of the Academy Award for Best Picture.  From greatest to least great, here's the '60s.

1. Midnight Cowboy (1969) - The only X-rated film that ever won Best Picture was a complete 180 from the previous year's winner "Oliver!"  It's still one of the darkest New Hollywood films, featuring a pair of small time hustlers, played by Jon Voight and Dustin Hoffman, who try to survive New York together.   It's a perfect snapshot of the end of the '60s, and a signal to the Hollywood establishment that more challenging films about adult subjects were here to stay.

2. The Sound of Music (1965) - This is a strong contender for my favorite musical, a rousing family and love story told in the grandest terms possible.  The songs are endlessly singable, Julie Andrews lights up the screen, and Austria has never looked so picturesque.  The only real competition "Sound of Music" had in the Best Picture race was David Lean's epic "Doctor Zhivago."  "Sound of Music" proved far more enduring, still regularly being broadcast on television to this day.

3. In the Heat of the Night (1967) - This year was the turning point where New Hollywood broke through, with nominees like "Bonnie and Clyde" and "The Graduate."  This was also the height of Sidney Poitier's success, who appeared in both "In the Heat of the Night" and "Guess Who's Coming to Dinner?"  Personally, I would have given the award to "The Graduate," but "In the Heat of the Night" is properly iconic in its own right, and still an excellent watch after all this time.

4. My Fair Lady (1964) - It beat out "Dr. Strangelove" and "Mary Poppins," and probably didn't deserve to.  And yet, I don't know how anyone could resist Audrey Hepburn and Rex Harrison in this movie.  Hepburn was famously considered the weak link in the film, which is ironic considering how beloved her Eliza Doolittle has become.  I think the biggest trouble is that "My Fair Lady" isn't very good as a musical, but it's an excellent romantic comedy and  farce, with production design to die for.  

5. Lawrence of Arabia (1962) - Some cineastes will be aghast that I have "Lawrence" ranked this low, but it's a film of very masculine concerns that I never connected to very well on any level but aesthetic appreciation for the epic filmmaking.  O'Toole should have gotten the Oscar instead of Gregory Peck, but as far as I'm concerned, "To Kill a Mockingbird" should have won Best Picture over "Lawrence of Arabia."

Shout out to Anne V. Coates for the greatest match cut of all time though.

6. The Apartment (1960) - I love a good Billy Wilder romantic comedy, and this is one of the best.  Jack Lemmon and Shirley MacLaine are so winning and so adorable as the leads, and these are the performances I remember them for best.  Wilder would work with both of them again in later films, like "Irma La Douce," but there was never that same chemistry, and the writing and humor were never quite as good.  "The Apartment" was far and away the obvious winter that year.

7. Oliver! (1968) - I'd argue that this was the last winner properly of the Old Hollywood tradition, an adventurous period musical produced by the Brits, improving on the stage version from which it was adapted.  It's better loved in the UK, where the musical is a staple of children's theater, but I've always been very fond of it too.  The kids are great, Ron Moody's Fagin is a treasure, and I still think of Oliver Reed first as the villainous Bill Sykes.  Still, "The Lion in Winter" should have won.   

8. West Side Story (1961) - Of the big musicals of this period, "West Side Story" is the one I'm the least attached to, despite knowing most of the songs inside and out.  The casting was always a big problem for me, and it aged so much worse than its contemporaries much faster.  I like the Spielberg remake so much better, I honestly feel a little bad about how little regard I have for this version.  It won Best Picture in a fairly weak year, against far more sedate dramas like "Judgment at Nuremberg."   

9. A Man For All Seasons (1966) - Now, I should add the qualifier that I haven't seen this film in about twenty years, but "A Man For All Seasons" always struck me as a particularly stately, drab morality play.  It's about Sir Thomas More standing up for virtue and decency in the face of King Henry VIII's antics, and essentially becoming a martyr for it.  Good cast and solid fundamentals, but I much prefer some of the other nominees, including "Who's Afraid of Virginia Woolf" and "Alfie."  

10. Tom Jones (1963) - The '60s were a much more sexually, er, exuberant time than I think many people realize, and "Tom Jones" is very much a film of that era and mindset.  Albert Finney playing an enthusiastically bawdy 18th century horndog is occasionally good for some hearty laughs, but I don't think I have to explain why it doesn't go down so easy in 2022.  Other contenders I'd have given the trophy to first include "Lilies of the Field," "America, America," and "Cleopatra."   

---