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We know them, we love them, and most of the time, we love to hate them. Regardless of how any of us feel about the iconic, troublesome teens that round out the fabric of Hollywood’s youth-centric media, they’ve left their signature messy marks. This list covers the big hitters, the unmistakable part-of-pop-culture adolescents who derailed monumentally (dependent on their character and world, not all misguided minors are created equal). Each calling card of these chaotic characters has a few things in common–they’re lost and faced with conflict–but how they solve their issues leads to many more issues than solutions. Buckle up and grab your favorite nostalgic mix tape/playlist; we’re in for a bumpy ride.
Jim Stark and Buzz Gunderson – Rebel Without a Cause
This is by far one of the most influential movies that jumpstarted the teen genre and it’s big thanks to Jim Stark (James Dean) and Buzz Gunderson (Corey Allen). When gang leader Buzz and new-in-town Jim agree to a “chickie race,” that’s when things go up in smoke. Jim is left to face the fallout.
Marissa Cooper – The O.C.
You could probably make a case for most of The O.C. kids, but Marissa Cooper (Mischa Barton) undoubtedly tops them all. Coop’s undoing was a monolith and started on the wings of her parents’ divorce. It led to underage drinking, tumultuous relationships, petty theft, and eventually to her passing away after a car crash at the end of Season 3.
Danny Zuko – Grease
Like many other ensembles, you could make a pick mostly anyone from the Grease cast, but Danny Zuko’s (John Travolta) issues bled into everyone else’s. Not to mention, he strung Sandy Olsson (Olivia Newton-John) along until the very end of the movie.
Serena van der Woodsen – Gossip Girl
Gossip Girl is another show where you could argue a good case for any of the characters being the biggest saboteur. But like Marissa Cooper, Serena van der Woodsen (Blake Lively) just can’t shake off trouble in most things she does. The thought of old her and Georgina Sparks together really sounds like they’d top the list together.
Veronica Sawyer – Heathers
Heathers and Veronica Sawyer (Winona Ryder) were ahead of the curve. When awkward loner Veronica gets invited to join the school’s most popular group, she quickly realizes it’s not the place for her. After befriending new kid Jason Dean (Christian Slater), they accidentally kill one of the Heathers. This sets off an entire killing spree that wreaks havoc on Westerburg High School.
Dawson Leery – Dawson’s Creek
Even though he may have been seen more as a golden boy during his reign, Dawson (James Van Der Beek) caused some major damage in his day. We literally have a separate list showcasing all the times Leery was the worst character for his loved ones to be around. If he’d only been supportive of Joey Potter (Katie Holmes) going to Paris, who knows what could’ve been?
Cady Heron – Mean Girls
Tina Fey’s wildly quotable Mean Girls needs no introduction or explanation. With Cady (Lindsay Lohan) coming to terms with attending a public high school in the US after growing up in Africa, she is a poster child for this list. As she explores her new reality, she gets lost for a moment amid girl world drama, which leads to multiple friend, family, and relationship troubles.
Rue Bennet – Euphoria
The Max ‘teen’ jewel-encrusted drama juggernaut holds another ensemble of lost and morose students. However, Rue Bennet (Zendaya) and her substance abuse issues are the focal point. It’s upended friendships, caused familial stresses, multiple times over, causing Rue to lie, steal and hurt everyone in the East Highlanders.
Chris Hargensen – Carrie
Stephen King’s Carrie is another classic high school staple that helped push the envelope on what fictional teen worlds could hold. Popular girl and bully, Chris Hargensen (Nancy Allen) makes Carrie’s (Sissy Spacek) life a living nightmare. Hargensen continues down a downward spiral that leads to the bone-chilling but iconic prank that happens at the dance (which has some truly grim consequences).
Tim Riggins – Friday Night Lights
If you know anything about this NBC network TV classic, you either love or hate Tim Riggins (Taylor Kitsch). While he was a regular womanizer, heavy partier, not to mention that he sabotaged himself and the team with some regularity, he straightened up.
Dallas ‘Dally’ Winston – The Outsiders
Francis Ford Coppola’s adaptation of The Outsiders is a quintessential coming-of-age story. Even though the whole gang is rough and tumble, along with any of the ‘Socs,’ Dally (Matt Dillon) is the most troubled. With an already tumultuous background, Johnny’s death sends him on to make poor decisions for himself and his friends.
Cory Matthews – Boy Meets World
Surprising, I know. The more classic choice from Boy Meets World may be Shawn Hunter, but Cory Matthews (Ben Savage) sparked plenty of trouble in his time (like fellow do-gooder, Dawson Leery). Throughout the 7 seasons, he caused more rifts between his family, friends and Topanga than anyone else.
Billy Loomis & Stu Macher – Scream
Naturally, any teen in any scary movie generally has some baggage that leads to strife in one way or another. Youths like Billy (Skeet Ulrich) and Stu (Matthew Lillard) are different, though, they are intentionally motivated to terrify and harm their fellow classmates and the people of Woodsboro. Unfortunately for them, their plans backfire on them gravely.
Lucas Scott – One Tree Hill
Like the aforementioned teen network drama shows of the mid and late ‘00s, any character is up for debate. Lucas Scott (Chad Michael Murray), the main protagonist, puts on a good show of commotion for everyone in his life. Being a serial heartbreaker while being unloyal and manipulative to others lands him this particular title.
Jennifer Check – Jennifer’s Body
Jennifer’s Body, again, isn’t filled with average adolescents, and especially not Jennifer (Megan Fox). While she and longtime friend Needy (Amanda Seyfried) head out for a semi-average night of Jennifer-approved fun, all goes awry. We find out that Jennifer has turned into a demon feasting on the male teens of Devil’s Kettle, WY. After the friends face off, Needy gets pinned for the murders and gets taken to an insane asylum.
Rachel Berry – Glee
The destined-for-greatness Rachel Berry (Lea Michele) typically stopped at nothing to get what she wanted, regardless of the consequences. While the fictional NYADA darling had moments of hope and promise, her ego and ambition always seemed to cause more harm than good. (Any Ryan Murphy-created teen could do, though.)
Seth – Superbad
The 2007 classic was the first Seth Rogen-Evan Goldberg project, and it immediately put them on the map. The semi-biographical Superbad revolves around characters with the same names and pretty typical senior tropes. Of the fictional duo Seth (Jonah Hill) and Evan (Michael Cera), and their pal, Fogell (Christopher Mintz-Plasse), the first of the trio creates the most trouble for their celebratory evening. While the trio make up, along with the girls (Emma Stone, Martha MacIsaac), before graduation.
Rory Gilmore – Gilmore Girls
“Why did you drop out of Yale?” Even though Rory Gilmore (Alexis Bledel) is one of the more unusual fictional high schoolers on the list, her dropping out was monumental for the world of Gilmore Girls. Even Lauren Graham didn’t like the storyline because of the turmoil it created between Lorelai and Rory. Not to mention, her sleeping with Dean, missing Lorelai’s graduation and later on, being more lost than ever in her 30s.
Donnie – Donnie Darko
Donnie (Jake Gyllenhaal) isn’t your typical troublesome, drama-filled teen, even though his choices in one reality lead to serious consequences. His present ED signifiers (Emotional Disturbance) present Donnie as something else, but we eventually come to realize he’s an anti-hero of sorts. As he comes to realize that there are multiple timelines at play, he chooses to fix it to save Gretchen Ross’ (Jena Malone) life. And with his developed powers, he returns to the day when it all went awry, which leads to his destiny–death.
Archie Andrews – Riverdale
Archie of The CW’s Riverdale was one of the many, much darker TV reboots out there. And though all the drama has always hinged on the red-headed football hero regardless of genre, the TV show really packs Archie with a punch. To be fair, he also found himself in the wrong place at the wrong time quite frequently–it’s how he reacted to them that gives him the top spot for the searching students of Riverdale High.
Kathryn Merteuil & Sebastian Valmont – Cruel Intentions
Another young and terrifying twosome is Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Philippe). The oddball step-siblings wager a bet that involves innocent and new Annette Hargrove (Reese Witherspoon). Through the scheme, the group of students is faced with continuing drama until a very sad end.
Valerie Malone – Beverly Hills, 90210
Though there was plenty of actual drama on the set of Beverly Hills, 90210, Valerie Malone (Tiffani Thiessen) wasted no time sowing seeds of chaos. Arriving in Season 5 with a lot of baggage in the form of family trauma, Malone was immediately set up to be in trouble. She dated many of the guys and regularly feuded with the girls.
Max Fischer – Rushmore
As one of the many stylized Wes Anderson films, Rushmore was one of his earliest. Max Fischer (Jason Schwartzman) is a love-drunk student determined to date his teacher and will stop at nothing to achieve it. After an array of mishaps and his fellow acquaintance, Blume (Bill Murray), hitting it off with her, Max loses it. He leaked the affair publicly and temporarily burned bridges with both of them.
Willow Rosenberg – Buffy The Vampire Slayer
Willow’s (Alyson Hannigan) rise to raising hell for Buffy and co. may be a slow burn, but once she hits it, things get wild. While her use of telepathy, manipulation and struggling to keep her magic in check kick off the season, Tara’s death sets Willow into overdrive in trying to destroy the world.
PJ & Josie – Bottoms
Gen Z coming-of-age comedies come in all shapes and sizes, including Emma Seligman’s Bottoms. The satirical take on the high school experience is wild, especially with PJ (Rachel Sennott) and Josie (Ayo Edebiri). The BFF’s hatch a fight club for girls so they can talk to cheerleaders they have crushes on. Needless to say, a lot of drama goes down, including a car blowing up.
Mona Vanderwaal – Pretty Little Liars
Honestly, most characters from the 2010 series have a fair shot here. But Mona (Janel Parrish) is the reason for all of the mystery and torment. She is who sparks the series because of her grudge against the main friend group. Eventually, she becomes one of them, and even more trouble ensues.
Laura Palmer – Twin Peaks: Fire Walk with Me
In my opinion, there’s no list about misguided high schoolers complete without Laura Palmer (Sheryl Lee). The character was cemented into pop culture in David Lynch’s cult show, Twin Peaks, but the less popular prequel movie shows her tragic undoing. Her last days are filled with traumas relating to her drug addiction, web of lies and darker spirits. Warning, this movie isn’t for the faint of heart.
DeGrassi: The Next Generation
DeGrassi: The Next Generation is maybe the only title on the list in which each character is as chaotic and troubled as the last. The iconic Canadian teen soap has multiple iterations, but the 2002-2015 series takes the cake. Between the students, they have every classic dramatic HS storyline in the book, and alumni Drake’s “I’m Upset” reunion-filled music video summarizes some key points.
Nancy Downs – The Craft
The quartet of girls in The Craft start as lost as the next, but Nancy’s (Fairuza Balk) power-hungry ways destroy what they have together. After quiet Sarah Bailey (Robin Tunney) moves to town and gets wronged, Downs and her pals take her in. All four hatch a scheme to cast a spell on the wrongdoer, and when it succeeds, that’s when Nancy starts sabotaging everything.
John B – Outer Banks
Netflix’s Outer Banks is one wild ride with wayward John B (Chase Stokes) at the helm. Sure, other characters may be outwardly more troubled (JJ, Sarah or Rafe), but everyone’s lives intensified because of John B’s initial treasure hunt.
Christine ‘Lady Bird’ McPherson – Lady Bird
As one of the more subtle teenage pot stirrers, Ladybird (Saoirse Ronan) still makes her presence and opinions unmistakably clear. Her main sources of conflict reside within her relationship with her hardworking mom (Laurie Metcalf) and nerdy best friend (Beanie Feldstein). While Lady Bird temporarily burns bridges with both in pursuit of greater life expectations and new friends, she mends things with both.
Effy Stonem – Skins UK
A cult classic that ran from 2007-2013 and largely featured the rebellious but lost Effy Stonem (Kaya Scodelario). From the jump, we see 14-year-old her sneaking home in the early morning after being out all night at a rave. Needless to say, Effy’s journey was a bumpy one filled with substance abuse, mental health crises, and a web of lies.