This qualifies as a Rewatchable movie, according to Bill Simmons. That is, one that when it comes on basic cable, you'll happy watch it again and remember why is was good at the time.
Cameron Diaz is Mary, a high school student in Rhode Island. The boys love her, and when Ted (Ben Stiller) screws up a chance to take her to the prom, he loses track of her, but never forgets her. So Ted hires a private eye, Pat (Matt Dillon) to find Mary. Pat goes down to Florida, and is so taken, that he decides to date her himself. When Ted finds out, he road trips to Florida with his friend Dom (Chris Elliott) to recapture the lost glory days.
Now that's a long description of a movie best remembered for Ben Stiller jacking off before his date with Mary, Ben Stiller getting his "frank and beans" caught in his zipper, Matt Dillon looking through windows as a peeping Tom (peeping Matt), and a general making fun of "retards", old Florida men and women, men who walk with crutches, musicians, and just about everyone else you can think of.
Surprisingly it works. The characters all have some heart and depth, especially ones who otherwise are made fun of: Tucker, Magda, Warren. Perhaps it's the complex plot, with multiple people all eventually meeting in the same room, like
Reservoir Dogs.
Tho whole premise is someone outdated in this Pre-Facebook/Google movie, when it was possible to move to Florida as an adult and everyone in your hometown to lose track of you. But the discovery of what the person turned out to me makes it a fun and interesting story, with lots of funny gags. Believe it or not, Cameron Diaz did not want to do the "hair gel" scene and it turned out to be the most iconic of her entire career.
A modern classic: * * * * *
