West Side Story (1961)
What is it? A retelling of the Romeo and Juliet story, but set on Manhattan's West Side amid warring Italian and Puerto Rican communities. Only these duelling gangs sing and dance!
Why did it win? The 50s musical hangover still lingering on may be a factor - but this is a cut above the rest, thanks to its, y'know, having a plot. And it's probably the case that even those Academy members who wanted to vote for fellow nominees The Guns of Navarone, Fanny, The Hustler and Judgment at Nuremberg were too busy humming I Want To Be In America to get around to it. That tune really does stick in the skull.
Did it deserve to win? Yes - this is one of those musicals that deserved the big prize, mixing as it does great tunes and athletic choreography with actual drama and social commentary. There were other good films that year - Yojimbo, The Hustler, Breakfast at Tiffany's, The Misfits - but none so outstanding that this feels out of place as a winner.
Worth a look? Does a gang member pirouette in the 'hood?