Last Updated on August 3, 2021
1. Ferris Bueller – FERRIS BUELLER’S DAY OFF (1986)
Has there ever been a cooler teenager in the history of the world? He’s got the perfect girlfriend, a hilarious best friend, an ass kicking sister, the dumbest parents on Earth, and a community that pulls together whenever he’s a little under the weather. Throw all that together on a day that included catching a foul ball at Wrigley Field, singing ‘Twist and Shout’ at the German-American Appreciation Day Parade, using a mini trampoline to soar around the backyards of sunbathing hotties, and almost indirectly causing the death of his principal.
2. The Breakfast Club – THE BREAKFAST CLUB (1985)
Everybody learns something in Hughes’ masterpiece. Outcasts learn being pretty leads to acceptance. Jocks learn Outcasts can be little hotties with some work. Princesses find sexiness in Rebels. Rebels discover if the carpet matches the drapes. And Nerds, well, Nerds accept the fact that they’ll never get laid but their penmanship is outstanding.
3. Del Griffith – PLANES, TRAINS, & AUTOMOBILES (1987)
John Candy was never better than he was as Del Griffith, the jolly shower ring salesman with a hint of social retardation. He’s the guy you like to watch from a distance but never hang out with. If there were more people like Del around the world would be a better place, and on the constant brink of destruction, and there’d be giant underwear everywhere.
4. Clark Griswold – VACATION (1983)
The man loves to travel, and each time he does he takes a different set of kids along for the ride. Clark (Chevy Chase) finds himself in more f*cked up situations than Michael Jackson at Disneyland and still comes out looking like the greatest dad in world before the credits role. My dad drives me across the country to an amusement park and it’s closed, somebody is dying. And it’s probably me.
5. Samantha Baker & Andie Walsh – SIXTEEN CANDLES (’84) & PRETTY IN PINK (’86)
Before teenage role models became plastic whores with no talent, Molly Ringwald owned many a heart during the eighties. These two characters combined experienced enough awkward situations and heartbreak to institutionalize an entire generation. Sam and Andie made it out okay though, even if they were probably single and pregnant before collage.
6. Farmer ‘The Geek’ Ted – SIXTEEN CANDLES (1984)
The king of all losers proves to be pretty cool by scamming the panties off a fire-bush, hanging out with the most popular guy in school, and hooking up with said popular guy’s sloppy seconds after the party of the year. The infamous headset brace set was never cooler.
7. Lisa – WEIRD SCIENCE (1985)
The perfect woman? Maybe, but wouldn’t things be even better if she constantly wore a nacho hat and owned a sports team that she let you bet on nightly? Lisa (Kelly LeBrock) looks hot and teaches us all how to be real men by never having sex and putting us in situations that will get our asses kicked. What more do you want?
8. Long Duk Dong – SIXTEEN CANDLES (1984)
We had a foreign exchange when I was in high school that I called Long Duk Dong for the better part of two years. I think she was German. The Donger (Gedde Watanabe) doesn’t waste any scenes here as he’s either drunk or having Lumberjack yankie his wankie for the majority of the film and straight into the minor character hall of fame.
9. Buck Russell – UNCLE BUCK (1989)
The slob with a heart of gold. Buck (John Candy) goes from bumbling buffoon to virginity saving hero in a matter of cleverly edited days. Who hasn’t tried making a batch of gigantic pancakes after seeing this movie? Me, that’s who. I f*cking hate pancakes, yo.
10. Watts – SOME KIND OF WONDERFUL (1987)
Very much the female version of Duckie (Jon Cryer in PRETTY IN PINK) only less of a pussy. Watts (Mary Stuart Masterson) may look and act like a lesbian with her sweet-ass leather ensemble and handy drumsticks but she turns out to be more than enough woman for Keith “I’ll take any piece of ass I can get” Nelson (Eric Stoltz).
Honourable Mentions: Cousin Eddie (VACATION), Duckie (PRETTY IN PINK), Kevin (HOME ALONE), Jack Butler (MR. MOM), Chet (WEIRD SCIENCE), Josie (CAREER OPPORTUNITIES), and Jake Briggs (SHE’S HAVING A BABY)
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