Rain Man (1988)
What is it? Tom Cruise plays Charlie Babbitt, a wheeler-dealer who expects a big inheritance when his father dies - only to learn that it has gone to the autistic brother (Dustin Hoffman) he never knew he had.
Why did it win? A majority of Oscar voters are actors, and acting roles don't come much more impressive than Dustin Hoffman's Oscar-winning turn as Raymond Babbitt. Besides, Cruise's turn - arguably the moment when he turned from boy wonder to megastar - is a masterpiece of (relative) understatement, and the film as a whole is well put together and better than the many parodies since would make you think.
Did it deserve to win? Not a disreputable one, but as usual that the best films of the year were genre efforts (the mighty Die Hard, Who Framed Roger Rabbit, Bull Durham) or fatally foreign (Cinema Paradiso, Women on the Verge of a Nervous Breakdown). Among the nominees, it beat acting-y drama The Accidental Tourist, period intrigue in Dangerous Liaisons, racial tension in Mississippi Burning and sparkling yuppie comedy in Working Girl.
Worth a look? Yes: it's a superior road movie with great performances.