This movie takes the top honors in this ranking, as it incorporates humor with some actual golfing.
Roy "Tin Cup" McAvoy (Kevin Costner) owns his own driving range, essentially his only sanctum. A former golf prodigy with nothing left, he teaches golf lessons out of his range. When Dr. Molly Griswold takes a lesson, she asks Roy to teach him. As a clinical psychologist, she quickly sees through his attempts to catch her eye.
David Simms, Molly's girlfriend, asks Roy to caddy for him. When facing a 230-yard shot, McAvoy criticizes Simms for laying up. Things escalate, and a bet is made. Roy flushes the shot, but is fired after.
Roy then decides he is going to qualify for the US Open. However, he also tries to get Molly, getting her assistance. They arrange a deal, she will help him rebuild his confidence in exchange for golf lessons. As it would have it, Tin Cup qualifies, but he seems to struggle from the issues on course, finishing his round with a seven iron.
In the final round of the US Open, McAvoy is in the heat of the tournament, and one decision to lay up or go for it makes or breaks him.
This movie tops this list for the reasons that it incorporates a real golf story in with humor. Unlike the others, the plot is less comedic, and actually has some meaning.