These well-known, sometimes loved and often hated characters from popular Hollywood teen series have made quite an impact, leaving behind a trail of chaos as they go. We’ve compiled a list of the most memorable troubled teens who, despite their varying degrees of misconduct, have left indelible marks on pop culture. Although each character deals with loss and conflict differently, their attempts to solve problems often create more problems than solutions. So, grab your favorite nostalgic playlist, because we’re about to embark on a rollercoaster ride through memory lane!
Jim Stark and Buzz Gunderson – Rebel Without a Cause
As a movie enthusiast, let me share that one of the most impactful films I’ve seen, which essentially paved the way for the teen genre, was none other than “Rebel Without a Cause.” The compelling performances by James Dean as Jim Stark and Corey Allen as Buzz Gunderson truly made this film stand out. The moment these two characters agreed to a so-called “chickie race,” things took a dramatic turn for the worse, leaving the newcomer, Jim, to deal with the repercussions.
Marissa Cooper – The O.C.
Among the characters from “The O.C.”, Marissa Cooper (Mischa Barton) stands out as the most complex and troubled. Her story began with the fallout from her parents’ divorce, which set off a series of events including underage drinking, turbulent relationships, small-time theft, and ultimately, her tragic death in a car accident at the end of Season 3.
Danny Zuko – Grease
Similar to other groups in the film, one could select any member from the cast of “Grease”, but it was Danny Zuko (John Travolta) who seemed to have personal struggles that affected everyone around him. Furthermore, he kept Sandy Olsson (Olivia Newton-John) waiting until the final moments of the movie before resolving their relationship.
Serena van der Woodsen – Gossip Girl
In another series similar to “Gossip Girl”, it’s not hard to make a convincing argument that any character could be the main troublemaker. However, much like Marissa Cooper, Serena van der Woodsen (played by Blake Lively) often finds herself entangled in turmoil in many of her actions. The idea of Serena and Georgina Sparks uniting seems almost certain to place them at the top of any troublemakers list.
Veronica Sawyer – Heathers
Heathers and Veronica Sawyer (played by Winona Ryder) were trailblazers, setting trends before others could catch up. When the shy outcast Veronica was unexpectedly invited to join the elite clique at her school, she soon discovered it wasn’t the right fit for her. After meeting the new student, Jason Dean (Christian Slater), they unintentionally ended the life of one of the Heathers, sparking a series of killings that created chaos within Westerburg High School.
Dawson Leery – Dawson’s Creek
Despite being known as a golden ruler during his reign, Dawson (James Van Der Beek) inflicted significant harm on several occasions. In fact, we have a distinct list that highlights all the instances when Leery was detrimental to those around him. If he had simply backed Joey Potter’s (Katie Holmes) decision to go to Paris, it could have led to entirely different outcomes.
Cady Heron – Mean Girls
Tina Fey’s popular movie “Mean Girls,” with Lindsay Lohan playing the role of Cady who transitions from life in Africa to an American high school, serves as an instantly recognizable example. Cady, fresh from her unique background, finds herself navigating the complexities of teenage life, only to stumble into a whirlwind of interpersonal conflicts involving friendships, family, and relationships.
Rue Bennet – Euphoria
In a different yet clear wording: The glitzy ‘Max teen’ saga, packed with jewels, continues with a new cast of melancholic students at its core. Yet, it’s the struggles of Rue Bennett (portrayed by Zendaya), battling substance addiction, that take center stage. Her challenges lead to fractured friendships, family strains, and deception – all compounding, pushing Rue to resort to dishonesty, theft, and causing pain to her fellow East Highlanders.
Chris Hargensen – Carrie
Stephen King’s novel Carrie is another timeless high school tale that challenged boundaries in fictional teenage environments. The antagonist, Chris Hargensen (portrayed by Nancy Allen), tormented Carrie (played by Sissy Spacek) mercilessly, making her life a misery. As the story unfolds, Hargensen’s actions lead to the infamous prank at the dance, which has tragic repercussions.
Tim Riggins – Friday Night Lights
If you’re familiar with the NBC network TV show classic, your feelings towards Tim Riggis (played by Taylor Kitsch) are likely either strong affection or dislike. Despite his frequent womanizing, heavy partying, and occasional self-sabotage that also impacted the team, he managed to reform himself.
Dallas ‘Dally’ Winston – The Outsiders
Francis Ford Coppola’s film version of “The Outsiders” showcases a classic tale about growing up. Despite their rough exterior, Dally (portrayed by Matt Dillon) stands out as the most conflicted among the group, even when compared to the ‘Socs.’ The death of Johnny leaves him in a precarious position, leading him to make questionable choices that affect not only himself but also his companions.
Cory Matthews – Boy Meets World
It might come as a shock, but while Shawn Hunter is often the one associated with causing trouble on “Boy Meets World”, it was actually Cory Matthews (played by Ben Savage) who stirred up quite a bit of drama over the course of the series. In fact, he managed to create more disagreements among his family, friends, and Topanga than any other character.
Billy Loomis & Stu Macher – Scream
As a movie-goer, it’s common to find that the teen characters in horror films often carry some sort of personal burden that contributes to conflict. However, Billy (Skeet Ulrich) and Stu (Matthew Lillard), unlike most, actively seek to terrorize and hurt their fellow students and the townsfolk of Woodsboro. Unfortunately for them, their schemes end up biting them back hard.
Lucas Scott – One Tree Hill
Similar to the teen network dramas popular in the mid to late ’00s, any character can be questioned or debated. The main protagonist, Lucas Scott (Chad Michael Murray), often gives the impression of chaos for those around him. His habitual breaking of hearts and unfaithful and manipulative behavior towards others earns him this specific label.
Jennifer Check – Jennifer’s Body
In a different take, “Jennifer’s Body” isn’t your typical teenage story, especially not for Jennifer (Megan Fox). Alongside her long-time companion Needy (Amanda Seyfried), they embark on a relatively ordinary night of entertainment that Jennifer approves. However, things quickly spiral out of control. It is revealed that Jennifer has transformed into a demonic entity feeding on the male teenagers of Devil’s Kettle, WY. Following their confrontation, Needy is falsely accused of the murders and institutionalized in an asylum.
Rachel Berry – Glee
Rachel Berry, portrayed by Lea Michele in Ryan Murphy’s creations, was relentless in pursuing her dreams, even if it meant overstepping boundaries. Despite flashes of potential and optimism, her self-importance and ambition often led to more trouble than success. (A character reminiscent of Ryan Murphy’s teenage characters.)
Seth – Superbad
2007 marked the debut of Seth Rogen and Evan Goldberg’s initial collaborative effort, which was none other than “Superbad.” This film catapulted them into prominence right away. The movie is a semi-autobiographical tale centered around characters named Seth (portrayed by Jonah Hill), Evan (Michael Cera), and their friend Fogell (Christopher Mintz-Plasse). It’s worth noting that the character causing the most chaos on their memorable night out is none other than the first of this trio, Seth. As the story unfolds, the trio eventually reconciles with the girls, Emma Stone and Martha MacIsaac, before they graduate.
Rory Gilmore – Gilmore Girls
Can you explain why you left Yale University?” The decision for Rory Gilmore (Alexis Bledel) to leave was a significant turning point in the series Gilmore Girls. This event caused quite a stir and added tension between Rory and Lorelai, as portrayed by Lauren Graham. Additionally, it led to events such as her relationship with Dean, missing Lorelai’s graduation, and ultimately finding herself aimlessly in her 30s.
Donnie – Donnie Darko
In a different take, Donnie (portrayed by Jake Gyllenhaal) isn’t your ordinary troubled teen who creates chaos and drama, despite the fact that some of his decisions in one reality have severe repercussions. Instead, his current indicators suggest emotional disturbance, but it becomes clear that he is more like an anti-hero figure. As he uncovers the existence of multiple realities, he makes a conscious effort to correct them to save Gretchen Ross’ (Jena Malone) life. With his growing abilities, he then travels back in time to the day when everything went wrong, leading him on a path to his fatedeath.
Archie Andrews – Riverdale
Archie from The CW’s series “Riverdale” is one of many television reboots with a darker tone. Despite the genre, the show delivers Archie in a powerful way. Interestingly, he often finds himself in troublesome situations that aren’t necessarily of his making, but it’s how he handles these predicaments that earns him the top spot among the inquisitive students at Riverdale High.
Kathryn Merteuil & Sebastian Valmont – Cruel Intentions
A pair of young and unsettling duo comprises Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Philippe), who are not blood-related but share an unusual bond. Their unconventional relationship leads to a daring wager that ensnares the unsuspecting Annette Hargrove (Reese Witherspoon). This game of intrigue sets off a chain of events, resulting in ongoing turmoil for the students until a tragic conclusion unfolds.
Valerie Malone – Beverly Hills, 90210
On the set of Beverly Hills, 90210, Valerie Malone (Tiffani Thiessen) quickly stirred up turmoil. Entering in Season 5 with a load of personal strife due to family issues, Malone was bound for conflict from the start. She got involved romantically with several guys and often clashed with other women.
Max Fischer – Rushmore
In a similar vein to Wes Anderson’s distinctive filmmaking style, “Rushmore” was one of his initial productions. The character Max Fischer, portrayed by Jason Schwartzman, is smitten beyond reason and intent on courting his teacher. He goes to great lengths to make this happen, often causing chaos along the way. However, when Blume (played by Bill Murray) begins a relationship with her, Max’s actions escalate to the point of revealing their affair publicly and damaging relationships with both parties temporarily.
Willow Rosenberg – Buffy The Vampire Slayer
Willow (played by Alyson Hannigan) gradually causes mayhem for Buffy and the gang, but when she reaches her peak, things get chaotic. Her skills with telepathy, manipulation, and trying to control her magic initiate the season, but Tara’s death pushes Willow into a frenzy, seeking to destroy the world.
PJ & Josie – Bottoms
Gen Z coming-of-age comedies are diverse in their forms, and one such example is Emma Seligman’s “Bottoms“. This film offers a humorous perspective on the high school life, with PJ (Rachel Sennott) and Josie (Ayo Edebiri) providing an outrageous portrayal. Their friendship leads to an unconventional solution – establishing a fight club for girls, aiming to engage with cheerleaders they admire romantically. Naturally, plenty of drama unfolds, culminating in a car explosion.
Mona Vanderwaal – Pretty Little Liars
To put it simply, nearly every character from the 2010 series has a good chance in this context. However, Mona (Janel Parrish) is instrumental in creating the mystery and turmoil that drives the story. Her long-standing grudge against the main group sets the plot in motion. Over time, she becomes part of their circle, which only adds to the trouble.
Laura Palmer – Twin Peaks: Fire Walk with Me
In my view, any list discussing misguided high school characters would be incomplete without Laura Palmer (played by Sheryl Lee). This character became iconic through David Lynch’s cult TV series, Twin Peaks, although her troubled past is further explored in the less well-known prequel film. The movie depicts her final days, which are marked by drug addiction, deceit, and encounters with dark forces. Please be aware that this movie may not be suitable for sensitive viewers.
DeGrassi: The Next Generation
DeGrassi: The Next Generation stands out among the titles on the list as every character is equally chaotic and troubled. This iconic Canadian teen soap opera has several versions, but the 2002-2015 series takes the lead. The students in this show cover all the classic dramatic high school storylines. Drake, one of the alumni, summarizes some key points from the series with his “I’m Upset” music video filled with reunion scenes.
Nancy Downs – The Craft
In the movie ‘The Craft’, a group of four girls initially struggle to find their place, but it’s Nancy (played by Fairuza Balk) who becomes power-hungry and ultimately ruins their bond. After Sarah Bailey (Robin Tunney) arrives in town and experiences injustice, Nancy and her friends decide to help her. Together, they concoct a plan to cast a spell on the offender, but when the spell works, it’s then that Nancy begins to undermine everything.
John B – Outer Banks
The adventurous Netflix series, “Outer Banks,” takes a thrilling journey with the charismatic John B (Chase Stokes) in command. While characters like JJ, Sarah, or Rafe might appear to have more obvious troubles, their lives became more entangled due to John B’s initial quest for treasure.
Christine ‘Lady Bird’ McPherson – Lady Bird
In a subtly assertive manner, Ladybird (Saoirse Ronan), one of the more quiet instigators among teenagers, effectively communicates her presence and viewpoints without any doubt. The primary sources of friction in her life stem from her dynamic with her diligent mother (Laurie Metcalf) and intellectually inclined best friend (Beanie Feldstein). At times, Ladybird strains relationships with both as she chases broader life aspirations and new acquaintances, but eventually reconciles with them both.
Effy Stonem – Skins UK
A well-known television series that aired from 2007 to 2013, primarily centered around the character of Effy Stonem (played by Kaya Scodelario). The story begins with 14-year-old Effy returning home in the wee hours following an all-night rave. It’s clear that Effy’s life was marked by a tumultuous path, including struggles with substance abuse, mental health issues, and deception.
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2025-04-19 20:40