5. Caddyshack II-
What can I say? There aren't that many golf movies.
4. The Legend of Bagger Vance-
Directed by Robert Redford it is a unique film that perfectly demonstrates "The Thing and the Other Thing" school of storytelling. It was based on a book by Steven Pressfield, best known for his atrocious novel Gates of Fire. One of the really great things about this film is actually the soundtrack which is filled with some really great entries from early 1930's jazz.
3. Caddyshack-
This one really doesn't need an explanation. Harold Ramis hits this one out of the park in one of the funniest and dirtiest movies of the period. The Baby Ruth in the pool, the playing through scene, and Bill Murray's attempts to catch the moles are all hilarious.
2. Happy Gilmore-
A lot of people will look at the rise in popularity that golf achieved at the end of the 90's and give all of the credit to Tiger Woods. While this is surely true, I think that both golf and Tiger benefited from the popularity of this Adam Sandler vehicle. This film also started the trend of sports comedies that feature a prominent actor in an individual sport (as opposed to a team), which has been taken to the limit by Will Ferrell. Adam Sandler went on a nice little run of funny movies that were named after the lead character.
1. Tin Cup-
One of the finest Kevin Costner films. You have to love the "going for it" mentality. I don't know why, but to me,the combination of the comeback story and the fact that Costner really nails his roles in sports movies makes this highly inspirational fare.
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