From the pits of the $5 bin at Wal-Mart comes Captain Ron. One of my weaknesses is for DVDs under $10, though increasingly I'll wait for a movie to make it to the $5 range. When I was a kid, I really liked this movie. It stars Martin Short as an up-tight father who inherits a sail boat from his uncle. He takes his family down to the Caribbean to sail the boat back to the US where he'll sell it. The boat is in considerably worse condition than he'd expected it to be, so the auction house sends the less-than-reputable Captain Ron Rico, played by Kurt Russell, to help the family sail the boat back. Along the way they realize that appearances can be deceiving and that quality time can be found even in the most dire of circumstances.
Kurt Russell's laid back crazy is paired perfectly with Martin Short's up-tight crazy. The two work well together. In a lot of ways there is a battle of masculinity at play in this movie. Russell represents a more primal version of masculinity. He is overtly sexual and has obviously seen a great deal of violence in his past (as his missing eye attests to). He is also a more desirable physical specimen than Short, often walking around in a bright orange Speedo. Martin on the other hand represents the modern corporate man. He gets ahead based on his mind, and less his physicality. Throughout the film, he fears that Russell's more hegemonic masculinity will usurp his own place as the head of his family. In the end, Short loosens up his thinking masculinity and adopts some of Russell's, even taking on an impression of Russell. Of course, Short's diminutive nature would prevent him from ever fully embodying the same hegemonic masculinity that Russell does, but with an attitude adjustment he may be partly there.
The humor in this film derives largely from a fish out of water formula. As a result a lot of slap-stick exists throughout as Short fails to react in time to the dangers of the open ocean. There are also a lot of great lines throughout the movie. The film asks what happens when an average family is placed in extraordinary circumstances, and it answers with laughs. Check it out if you have the time.