5 best golf movies ever made: Caddyshack isn't No. 1

4. The Greatest Game Ever Played (2005)

Starting: Shia Labeouf, Stephen Dillane, Josh Flitter, Elias Koteas

Based on the events leading up to and surrounding the 1913 US Open, the film focuses primarily on Francis Ouimet (Labeouf), who came from a poor Massachusetts family and made his early living caddying at The Country Club in Brookline.

At the time, golf was a "gentleman's game", and those from poor backgrounds were considered second-class citizens on the course. Even Harry Vardon (Dillane), who at this time had won five British Opens and a US Open, was considered unworthy of membership a the prestigious country club because he came from a poor upbringing.

In an attempt to show Americans that the English were the best golfers on the planet (like USA Basketball), they sent Vardon, Ted Ray, and amateur champion Wilfrid Reid to play in the US Open and win it decisively. Ouimet made it into the US Open field by way of a qualifier, and the rest is literally history (check Wikipedia for spoilers). 

The acting in this film is fantastic, and the story is compelling. I never get tired of seeing it, and if you like golf and the way Disney does sports movies, you'll enjoy this film as well. It's always fun to see the equipment and dress of golfers in the early days.