A sentimental pick, if only because it marks the last feature film appearance of Cary Grant. It's also a cute movie that is a remake of the equally cute The More the Merrier, transporting the story to Tokyo during the 1964 Olympics where a housing shortage finds Grant's businessman sharing an apartment with a young woman and an Olympic hopeful and trying to play matchmaker between them. It's a breezy and inconsequential movie, but it's pretty delightful.
Michael Ritchie's Downhill Racer, which stars Robert Redford as a skier who competes in the 1968 Olympics, is one of the great movies about athletes. Not one of the great movies about sports, necessarily, but rather about the mindset, the drive, and the narrow focus of an athlete trying to compete at the top level of their sport. Redford's character isn't really a likeable guy, but that's the point: he's channeled so much of himself into his pursuit of glory that there's nothing left for being a human being.
Is The Cutting Edge a brilliant work of art? No, not even close. But it is an extremely watchable movie, no matter how cheesy it might be. If you're a woman in your 30s, you've probably seen this romantic comedy about a figure skater and the ex-hockey player who is recruited to be her pairs partner in the 1992 Olympics at least once. It was, after all, on TV all the time in the '90s and became something of a slumber party staple. Ask just about any woman between the ages of 30 and 40 what she thinks when she hears the term "toe pick," and she'll name this movie.
The story of the Jamaican bobsled team is one of the most enduring feelgood stories in Olympic history thanks in no small part to Cool Runnings, the film which dramatizes (and takes several liberties with) their story. Like The Cutting Edge, Cool Runnings isn't exactly brilliant cinema, but it's pretty damn entertaining.
It's hard to argue with 4 Oscars (plus 3 more nominations), including one for Best Picture. I bet that music is already stuck in your head.