How old do you have to be to be too old for a High School movie?  Pretty freaking old is what I’m thinking.  Some of the best movies around can be stuck into this special little category.  This is a group that dominates both our hearts and the box office.  My original brainstorming list had 27 movies on it.  I had to be talked down to 10 my girl Rox (Thanks!) and a lot of research because I felt that I simply couldn’t cut any of the films from the gigantic list. It hurt my soul to whack some of them.  But, here’s what it boiled down to, the best of the best.  Is your favorite missing?  Then, stop muttering at your computer screen and leave a comment!  Represent!

10. Superbad (2007)

If you weren’t charmed by McLovin’, your heart is made of ice.  That’s the only explanation.  Awkward coming-of-age goodness with a heavy side of dirty talk.  Michael Cera and Jonah Hill are adorable, unlikely heroes for a whole new generation of teenagers, a fact that helps me sleep at night.

9.  Election (1999)

This dark comedy is witty and cutting and leaves you with a funny feeling in your stomach, and not just from laughing so hard.  Reese Witherspoon‘s Tracy Flick is such a spot-on portrayal of that Type A loser you hated in high school, you’ll want to cheer and puke.

8.  Dazed and Confused (1993)

It’s the last day of school at a Texas high school in the 1970′s.  What’s there to do?  Party at the moon tower!  Richard Linklater has made my life complete with his hilarious and nostalgic tribute to the good ole’ days.  (It will make you happy no matter what year you graduated, trust me.)  Watch it for the amazing ensemble cast and to count the weed references.  That would be a great drinking game if you are so inclined.  You should probably get on that.

7.  Pretty In Pink (1986)

Quintessential New Wave viewing.  This film was completely necessary for kids in the 80′s to learn the proper way to wear broaches without looking like Grandma.  Director John Hughes and his muse Molly Ringwald tell a story that is perhaps cliche but ultimately hopeful.  I am forever on Team Duckie.

6. Rushmore (1998)

I think this is Wes Anderson‘s best flick so far and the performances by Bill Murray and Jason Schwartzman are straight up brilliant.  It’s funny as hell but there’s something so real and pathetic about these characters that it almost makes you depressed.  Almost.  You won’t have any trouble both laughing at and rooting for them.

5.  Clueless (1995)

Amy Heckerling does it Beverly Hills style with this precious but snarky look at high school life for rich kids. Cher (Alicia Silverstone) is sweet and, aptly clueless but you’ll be sucked right into the world and the plot. It’s so much fun to watch. Just try not to say “As if,” afterward in public. Because you’ll, like, look dumb.

4. Ferris Bueller’s Day Off (1986)

John Hughes says another high school f-you to the establishment in this excellent comedy. Matthew Broderick stars as Ferris Bueller, perhaps the most lovable teen of all time. This film takes a crime like skipping school, holds it up before the light, and pronounces it necessary!

3. Heathers (1989)

The poster child for Cult Classic, this is one of those films you wouldn’t dare put down in, say my presence.  A dark, biting satire with a great cast (Winona Ryder, Christian Slater), this movie takes all your teen-angst urges and makes them a reality.  Flippin’ awesome.

2. Napoleon Dynamite (2004)

Nerds rock! This film will take you to that painful laughter place. You know the one I mean, where you think you might die but you’re stoked. The movie has a timeless feel to it, where the characters could be trapped in the 80′s, or, as is the case here, in Iowa. Classic underdog-makes-good formula outrageously geekified.

1.  The Breakfast Club (1985)

Like Jean-Paul Sartre’s No Exit but for teenagers.  Detention is like hell, right?  In John Hughes’ masterpiece, five kids from different cliques work out their problems in one long, hilarious day.  You cannot help but love this flick.  Seriously, you can’t.  If you say you don’t like it, I think you’re lying.  Maybe you should spend a day in detention and think about what you’ve done.

Honorable Mention:  Juno (2007), Fast Times at Ridgemont High (1982), Mean Girls (2004) and The Outsiders (1983).