Another famous Oscar misfire.

Of course, and maybe it would have been the big winner if Gene Kelly's An American in Paris hadn't had a somewhat come-from-behind victory just the year before. Plus, compared to that film, Singin' in the Rain would have been considered more slight, trivial, less cultured. The Academy loved its cultured films, Broadway adaptations, and travelogues in the 1950s and 1960s before realism, action, and emotional maturity took over in the 1970s.

But really, Singin' in the Rain just wasn't initially met with the great acclaim it has today, and I can't seem to find anyone who can explain it.

What should it have won?

At the very least:

Picture
Director
Supporting Actress (Gloria Grahame is forgettable in the role for which she won, and though she had a better, longer career than Jean Hagen, nothing she did topped Lina Lamont.)
Original Screenplay
Scoring-Adaptation (why did it lose?)

I'd probably throw it Editing over High Noon and Color Cinematography over The Quiet Man, but those both are debatable.

The tricky ones are Art Direction and Costume Design. Singin' definitely deserved those, but so did the actual winner, Moulin Rouge. I can see Moulin winning Art because of those French sets, whereas Singin' is mostly soundstages despite some wonderful elements in the "Gotta Dance" number and "Fit as a Fiddle." But Costumes I would have definitely given to Singin' because of the sheer volume. Moulin Rouge is an artistic film but can't compare to the depth and range of the Baz Luhrmann film, btw.

I haven't seen Viva Zapata! to know whether Anthony Quinn deserved his first Oscar over the not-nominated Donald O'Connor, but Quinn had at least two subsequent worthy performances (one of which actually won), so with hindsight on my side, I doubt I'd vote for him.

I can understand Gene Kelly not winning, but I doubt I would have given the sullen Gary Cooper another Oscar for High Noon either.

Ivanhoe was most likely the most undeserved, filler nomination of the year, though The Greatest Show on Earth apparently hasn't held up well either.

For my money there shouldn't even have been few to no other nominees. 1952 isn't exactly a banner year for undying filmmaking.

Keep in mind that the movie spoofs Hollywood, and Hollywood doesn't necessarily take to seeing itself portrayed onscreen, spoofed or otherwise.

"Sunset Boulevard" was nominated in 1951 for "Best Picture" but lost to "All About Eve". Seems Hollywood likes sardonic/tragic portrayals of actors but only if they're in the theater, not the cinema.

(None of the versions of "A Star Is Born" ever made it to "Best Picture"; the first version in 1938 was given an Oscar for the rather odd aspect of "Special Recognition" - but after that, nada.)

"Don't call me 'honey', mac."
"Don't call me 'mac'... HONEY!"