1. The Sandlot (1993)
Director: David M. Evans
Stars: Tom Guiry, Mike Vitar, Patrick Renna, Chauncey Leopardi, Marty York, Brandon Quintin Adams
Vacation destination: The neighborhood baseball field and the local pool
Maybe it's because our introduction to The Sandlot's scrappy crew coincided with our own youth, or because HBO played the movie every single morning the summer of '94 (a summer marked by the release of Green Day's Dookie, another pop culture landmark), but we can confidently declare that no other film epitomizes the restless spirit of summer vacation quite like this one.
Every amazing thing about a three-month hiatus from school was captured in this movie: baseball games whose players were limited to the kids on the adjacent blocks, meddling disguised as adventure (flesh-starved canine "The Beast" could easily stand in for any exaggerated obstacle we tangled with as kid), and most importantly, creeping on the Wendy's of the world (ie: whichever girls were developing the fastest and flaunting it the most).
We also owe our respects for the phrase "You're killing me, Smalls!", which is applicable in just about any situation, ever. Tip your hats, folks.