3. Say Anything (1989)
It's never a shock when an '80s babe falls in love with a John Cusack character, but none have done so as endearingly as class valedictorian Diane Court. Cusack plays Lloyd Dobbler, a quirky, well-traveled, aspiring kickboxer who seems to understand more about the meaning of life than most. This is basically the movie that ruined dating for all of us --just ask Chuck Klosterman who wrote about Cusack's characters destroying the modern meaning of love in his 2004 book Sex, Drugs, and Cocoa Puffs: A Low Culture Manifesto-- because Lloyd was so thoughtful and so romantic and their love was SO mindblowing it was just impossible to replicate IRL. Nevertheless, when Lloyd holds up the boombox blasting "In Your Eyes" outside of Diane's bedroom window, your heart will explode...and you'll believe in summer love again. Bonus points for Lili Taylor's collection of "Joe Lies" jilted-ex-lover style songs. Also, this was Cameron Crowe's directorial debut, not too shabby.
4. Stand By Me (1986)
This movie is perfect for any time of year but really captures that "finding yourself" feeling of a great summer flick. This is the heroic story of four best friends; Gordie, the bookish voice of reason who feels invisible; Chris, the youngest in a family of ruffians and drunks, who has a heart of gold; Vern, a chubby, shy, butt of the joke-type and the incomparable Teddy Duchamp, an eccentric spaz. Set in the 1950s the boys set out to find the body of missing boy in an effort to become local heroes. Along their journey they dodge trains, leeches and a gang of hoodlums all while discovering their own strength of conviction. Set against a perfect '50s soundtrack, Stand By Me is the archetypal coming of age story. It made me feel something when I was 12. Plus it stars a young River Phoenix and that's a wonderful treat.
5. The Parent Trap (1961)
Before Linsday Lohan shot to stardom in the 1998 remake, a young Hayley Mills portrayed the role of separated at birth twins Sharon and Susan. When the two identical twins--who never knew the other existed--meet by accident at summer camp, they decided the only logical thing to do is to switch parents. This way they'll get an opportunity to meet the parent they were taken away from and hopefully reunite their divorced parents. Their swap is discovered and Susan and their mother fly to California to switch the girls back but the twins are too smart for that noise. They dress alike to confuse everyone and work their magic to destroy their father's relationship with a young gold-digger and drive him back into the arms of their mother. This movie riveted me as a child, I even video taped it during one of the Disney Channel free preview weeks back when it was a subscription only channel.
6. One Crazy Summer (1986)
Here we once again meet John Cusack this time as Hoops McCann, a recent high school grad who has recently disappointed his family by failing to get a basketball scholarship. As his backup plan, Hoops strives to attend Rhode Island School of Design but must write and illustrate a love story for his application. He decides to spend the summer with his pals George and Squid on Nantucket. On their way to the island they pick up Cassandra (played by a young Demi Moore), a singer who also happens to be being chased by a motorcycle gang. Once on the island Hoops and his pals (including Bobcat Goldwaith) help Cassandra save her grandfather's house from the covetous Beckersted Family. They do irresponsible things with boats and '80s hilarity ensues.
7. Adventureland (2009)
Right after graduating from Oberlin College, James' summer European vacation plans fall through and he's forced to take a silly job at the local amusement park in Pittsburgh, PA. He befriends the park's hottest babe, Em and her sarcastic pal Joel. Together they eat pot-brownies on the job, outsmart game cheaters, and listen to The Velvet Underground. It's a summer of screwed-up romances, disappointing parents, and James finally losing his V-card. It has just the right amount of post-college nostalgia and hopefulness to feel realistic and it's all set to a perfect '80s new-wave/punk soundtrack.
8. The Sandlot (1993)
This is the kind of movie that makes you yearn for those adventure-filled childhood summers. Scotty Smalls moves to a new neighborhood and wants to learn to play baseball. Neighborhood baseball hot-shot Benny "the Jet" takes Smalls under his wing and before long he joins the motley crew of baseball boys. Together they navigate a summer full of baseball, tree-house sleepovers, the traveling fair and a gorgeous lifeguard at the local pool. Perhaps their biggest challenge is the ball-eating dog that resides just over the wall from their sand lot. "The Beast," as he's called, is a legendary force to be reckoned with but after the boys accidentally hit a Babe Ruth autographed ball into his yard, Benny has no choice but to swallow his fear retrieve it. This movie also contains one of the most quotable lines ever, "You're killin' me, Smalls."
9. Wet Hot American Summer (2001)
This ridiculous knee-slapper comes to us from the warped, precious minds of The State cast members Michael Showalter and David Wain. It's the last day of camp in 1981 and Camp Firewood counselors and staff have just a few hours to score with their summer conquests. While Susie and Ben work to organize the big end of summer talent show, Coop strives to win the affections of fellow counselor Katie. Since Coop can't hold a candle to her super hot yet totally unfaithful boyfriend Andy, he enlists the help of shell-shocked Vietnam vet camp cook Gene who shows him how to harness his awesome. Meanwhile, a bunch of goth kids and Niles from Fraiser stop a huge chuck of NASA's sky lab from colliding with the camp. Also, they do heroin and abandon some children on a river. It's a true American classic.
10. Dirty Dancing (1987)
The this is the quintessential summer escape. When Baby's family vacations in the Catskills in the summer of 1963, she develops a righteous crush on the resort's dance instructor Johnny Castle (played by the one and only Patrick Swayze). When Johnny's dance partner Penny gets knocked up by womanizing waiter and general d-bag Robbie, Baby steps in, securing the money for Penny's abortion and taking over for her on the dance floor. Tensions rise on and off the dance floor as Baby falls hard for Johnny. When Johnny is eventually accused of stealing a resort guest's wallet and can't provide an alibi, Baby confesses that she and Johnny were in his cabin doing adult things that night. Johnny gets canned but still makes an appearance at the resorts final talent competition with Baby by his side. Featuring a glorious soundtrack (complete with Swayze hit "She's Like The Wind") and the infamous quip "Nobody puts Baby in a corner," Dirty Dancing is just the best. Accept no imitations (that means don't bother with the remake, because nothing will be better than the original).