Won: My Fair Lady/Oliver!
Robbed: Dr. Strangelove/2001: A Space Odyssey
It's one thing, in a given year, for some confluence of fashion, shortsightedness, and luck to hand a mediocrity the big statue over a future classic. But there's something especially, even charmingly perverse about the two greatest films of the most critically revered American director of the last 50 years both losing out to that most ur-Hollywood of creatures, the big, splashy musical. (What are the odds?) While Stanley Kubrick was making cinematic and cultural history with Dr. Strangelove: or, How I Learned to Stop Worrying and Love the Bomb and 2001: A Space Odyssey, the Academy was paying homage to Cockney flower girls and pocket-picking moppets. (Only Strangelove was even nominated for Best Picture, although Kubrick did get Best Director nods for both films.)
Not that My Fair Lady and Oliver! aren't perfectly respectable examples of the form (particularly the devilishly entertaining Lady), outfitted as well with the Academy catnip of high-art origins (a Shaw play and a Dickens novel, respectively). But it stands as an elegantly perfect expression of Oscar-family values during the dying days of the bloated studio system that these all-singing/all-dancing Big Productions aced out Kubrick's thematically rich, aesthetically groundbreaking masterpieces. Exploring the biggest possible issues (humankind's destruction and humankind's creation) through daringly unexpected filters (nightmarish black comedy and space opera), Strangelove and 2001 couldn't be more different in visual and narrative style--a testament to the filmmaker's expansive artistic imagination. But both are immensely rewarding moviegoing experiences, intellectually stimulating and addictively watchable even after dozens of viewings. (As to the oft-repeated criticism that the stately, poetic 2001 is boring, try sitting through a couple of Oliver!'s interminable production numbers.) Kubrick did snag a statue for 2001's special effects (for which he rather arrogantly took sole credit), but he never did win as either a producer or director. He did get a nice tribute at the '99 Oscars, though, having conveniently died a few weeks before the ceremony.
They wuz robbed! 1942 - Sullivan's Travels
They wuz robbed! 1951 - A Place In The Sun
They wuz robbed! 1979 - Apocalypse Now
They wuz robbed! 1980 - Raging Bull
They wuz robbed! 1994 - Heavenly Creatures