Top 10 Most Awkward Teen Movie Characters
Mary Katherine Gallagher from “Superstar” (1999), Nadine Franklin from “The Edge of Seventeen” (2016) and Mia Thermopolis from “The Princess Diaries” (2001)!
#10: Peter Parker
“Spider-Man: Homecoming” (2017)
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When you think of a superhero, you probably imagine a strong silent type like Batman or Superman. But since his inception in the comics, Spider-Man has always been much more relatable as a younger character who doesn’t exactly have it all figured out. Tom Holland took on the role in the MCU for Spider-Man’s latest iteration, and brought an adorable bumbling quality to the character, which made him a figure that many teens could surely see themselves in. Just because you’ve got powers doesn’t mean you can’t be super awkward sometimes!
#9: James ‘Jim’ Levenstein
“American Pie” (1999)
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This late ‘90s teen sex comedy was chock full of gawkiness, and perhaps no one brought it more than the main character, Jim. Jim is your average teenage boy who is obsessed with sex and has some private practices that were built to make audiences recoil. It doesn’t help that his dad, played by Eugene Levy, is as uncomfortable as his son, always walking in at the most inopportune moments and offering unsolicited sexual advice. Everything that happens to Jim in this movie makes us want to cover our eyes in horror.
#8: Mary Katherine Gallagher
“Superstar” (1999)
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They just don’t make over-the-top, ridiculous teen comedies like this one anymore. The premise of “Superstar” is that a super dorky girl is trying to become, you guessed it, a superstar in order to gain the attention of the guy she is crushing on. Whether she’s asking god to send her someone to kiss, making out with trees, or sniffing her hands after shoving them into her armpits, Molly Shannon as Mary Katherine Gallagher is one big ball of awkward. Try not to cringe watching this one!
#7: Allison Reynolds
“The Breakfast Club” (1985)
The entire premise of “The Breakfast Club” is that five high school students from different cliques end up forced to spend a Saturday in detention together, and throughout the process learn how much they actually have in common. The least likely candidate to mesh with the other teens, however, is Allison, the resident weirdo who is about as unpredictable as they come. She’s not awkward in the typical sense, but rather makes you feel a deep unease at her bizarre statements and actions. The makeover at the end sure helps!
#6: Nadine Franklin
“The Edge of Seventeen” (2016)
Nadine is just a regular high school girl trying to make things work, but it seems like nothing can just be easy for her. Actress Hailee Steinfeld may be brimming with confidence in real life, but she does an excellent job playing the ever-awkward character. From the Pedro haircut to her angry outbursts, we can’t help but feel sorry for her. The part where she accidentally sends her crush a message that’s both soul-baring and sexually explicit makes our jaws drop every time we see it.
#5: George McFly
“Back to the Future” (1985)
Considering that Marty is a pretty cool kid, you’d think that his dad would be too. But when he’s sent back in time, he realizes that his dad is pretty much the biggest nerd there is. When Marty meets him, George McFly is being bullied by Biff, who has continued to antagonize him throughout their adult lives as well. Marty is forced into a position where he has to make sure that his parents get together, which is not an easy task considering just how dorky and bumbling George is. But hey, he gets it together when it really matters!
#4: Mia Thermopolis
“The Princess Diaries” (2001)
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The entire premise of this early aughts movie rests on the fact that the protagonist is about as awkward as they come. Mia Thermopolis, played by Anne Hathaway, is surprised to find out that she’s related to royalty and seems like the worst possible candidate to be a princess, considering her clumsiness, lack of grace, and generally uncouth demeanor. As the movie progresses, though, she transforms from an clumsy caterpillar to a poised butterfly in one of the best makeover transformations ever to be committed to film.
#3: Josie Geller
“Never Been Kissed” (1999)
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Drew Barrymore may be adorable as an adult in this movie, but when we get flashbacks to what she was like in high school, it’s pretty obvious why she never got her first kiss. Josie was a pretty big dork and was cruelly bullied, which only made her more insecure. Our hearts can’t help but break during flashbacks when she finds out that her crush asking her to the prom was all a big joke in order to humiliate her. Thankfully, she was able to shed her gawky persona and thrive as an adult.
#2: Fogell AKA ‘McLovin’
“Superbad” (2007)
Is there anyone more hilariously awkward than this character? Part of McLovin’s charm is his totally misplaced self-confidence, despite the fact that he is about as cringe-worthy as they come. “Superbad” is your classic teen comedy, with the male leads all attempting to lose their virginity before graduation and getting into plenty of trouble along the way. In many ways, Fogell represents geeky characters that have existed for decades in film, and he’s the perfect modern example of this common trope. To think, writers Seth Rogen and Evan Goldberg actually based this inept character on a real-life friend.
Before we unveil our top pick, here are a few honorable mentions:
Tai Frasier
“Clueless” (1995)
Minnie Goetze
“The Diary of a Teenage Girl” (2015)
Fat Amy Hobart
“Pitch Perfect” (2012)
#1: Napoleon Dynamite
“Napoleon Dynamite” (2004)
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Heck yes! We'd vote for you! You can’t exactly put this character in a box. Yes, he’s a huge dork and everything he does is so bizarre it makes you wince. But he’s definitely not your stereotypical nerd. Napoleon Dynamite has quirk and personality in spades, making him charming in his own weird way. In fact, this character was so iconic that he actually made life imitate art, creating a space for uncool to be cool again among teens. Where would we even be without him?
