18. Napoleon Dynamite
This movie might be branded an “acquired taste” or “love it or just don’t get it”. Made on an extremely low budget of around $400K, this goofy comedy follows Napoleon Dynamite, an eccentric, weird teenager (Jon Heder) who helps his friend Pedro (Efren Ramirez) run for student body president of their high school.
Despite the low budget, the production quality, script and acting are all top notch. Word of mouth spread quickly on the film and despite never being in the top 5 for weekend box office still made a respectable $44.5 million. The film gets a lot of things correct for the time and would be considered a “slice of life” type film not trying to be anything grand and just tell a funny, simple story. “Vote for Pedro!”
19. Pretty in Pink
One of the classic teenage love triangle films of the 1980s, Andie (Molly Ringwald) has to decide who she likes better, her friend “Duckie” (Jon Cryer) or new rich guy Blane (Andrew McCarthy) in another John Hughes classic. More “cliques” are on display here, mostly the “haves” and the “have nots” and the fact they do not mix together well without everyone talking. Teenage relationships can be very complicated often having many outside influences.
Another Hughes staple, Anthony Michael Hall, was going to play the “Duckie” role, but turned it down in fear of being typecast. As with other Hughes films of the time period, the film’s soundtrack featured a lot of new wave artists and music and was very highly regarded for its time. Another great “Brat Pack” film of the period.
20. Rebel Without a Cause
What can you say about James Dean? He is still the only actor to receive two posthumous Academy Award nominations, one for this film and one for “East of Eden”. This time he plays Jim, a troubled teen who moves to a new town to start a new life. He does not have a good relationship with his parents, so he seeks the approval of Judy (Natalie Wood). He eventually falls in with the wrong crowd getting involved in a dangerous race toward a seaside cliff.
The film was heralded for the fine acting performances from its teenage stars including Dean, Wood, Sal Mineo and Dennis Hopper. It is ironic three of these stars died premature, tragic deaths (Dean, Wood and Mineo).
21. Risky Business
It’s true Tom Cruise had made several films before sliding across the living room floor in his socks; however, it was this film that made everyone sit back and take notice of him. When his parents leave on vacation, teenager Joel (Cruise) decides to have some fun in their absence. He ends up calling a high class prostitute (Rebecca De Mornay) for some fun and things begin to become unhinged.
Needless to say, his father’s Porsche 928 and an expensive glass egg become involved and Joel has to come up with a plan to resolve the situation. Writer and director Paul Brickman tells a compelling, funny, poignant story which is a step above the other “sex comedies” of the period.
Wes Anderson began his directing career with “Bottle Rocket”. Although not financially successful, the film was received well by critics. His follow-up, “Rushmore”, had better box office results and really marked a transition for star Bill Murray from his “Caddyshack”, “Ghostbusters” characters to more serious but still funny “Anderson” roles including “The Royal Tenenbaums”, “The Life Aquatic with Steve Zissou” and “The Darjeeling Limited” which he is still doing today.
This film pairs Murray as a rich businessman who forms an unusual friendship with Jason Schwartzman as an over-achieving teen as they both have love for a first grade teacher (Olivia Williams). As with all Anderson films, eccentric characters and sharp, witty dialogue shine here and the result is a very memorable, dramedy.
23. Say Anything…
Cameron Crowe wrote and directed John Cusack and Ione Skye as Lloyd Dobler and Diane Court, two teens who develop a unlikely relationship even though Lloyd is very awkward and Diane is smart and very beautiful. After several courtship attempts, he is finally successful and has to make the most of their time together before she leaves the country on a scholarship. As with all Crowe stories, the characters are very well written as thorough, thoughtful, layered individuals.
As is the case with Diane’s father (the wonderful John Mahoney) who is a nice guy who takes care of the elderly until very unflattering details surface about his actions. It’s hard to believe Skye did not have a career as an A-list actress after this film as her performance was outstanding. The dialogue remembered from this film include “I gave her my heart, and she gave me a pen” and “I’m incarcerated, Lloyd!”
24. Sixteen Candles
Can you believe John Hughes only actually directed eight movies? Look at the list. Other than “Curly Sue” they are all truly great. “Sixteen Candles” is the one that started it all. Every element of the film would reappear later in other Hughes stories including teens who love others who don’t love them back, embarrassing teen moments, out of touch parents and grandparents and ultimate coming of age.
This time around, a teen has everything going wrong in her life when her family forgets her 16th birthday. She also has this annoying geeky kid in her high school who has a crush on her. Do you remember the line, “Can I borrow your underpants for 10 minutes?”
Long time partners Seth Rogen and Evan Goldberg wrote and produced this teen comedy which introduced the world to Seth, Evan and “McLovin” (Michael Cera, Jonah Hill, Christopher Mintz-Plasse.)
Seth and Evan are ending their time in high school and find themselves invited to a party and want to make a good impression by scoring lots of alcohol with the aid of McLovin to hopefully score some babes. Things go wrong when they decide to use a fake I.D. and two irresponsible cops (Seth Rogan and Bill Hader) become involved.
As with other films on this list, “Superbad” uses the best elements of comedy, vulgarity and sincerity to produce a hilarious, awkward film which showcases the hyper focused realities of high school.
Honorable mentions or this list include:
Can’t Buy Me Love
Friday Night Lights
Remember the Titans
Author Bio: Andy Kubica is a life-long cinephile. Having spend time as a video store manager, movie theater manager and the first DVD buyer for a former rental chain he now spends every waking moment reducing his film “bucket list”.