Teenage criminals have been the subject of big-screen stories for decades. Wayward youths are particularly sympathetic subjects, in part because they still seem to have such promising futures ahead of them.
The movies on this list, which are largely tragedies, focus on the terrible decisions that led each character to a horrible fate. More importantly, though, they highlight the systems that often leave teenagers, especially poor or marginalized teenagers, feeling like they have no choice but to become criminals.
Filmmakers on this list deserve some credit for how they portray these sensitive issues.
Rebel Without a Cause
Maybe the definitive film about teenage alienation, Rebel Without a Cause follows a teenager — played by James Dean — who finds himself unable to adjust to the new school he’s just moved to. Rebel Without a Cause may seem tame by today’s standards, but at the time, it was a revelation to watch a young man who appeared to have everything and still couldn’t find any way to be happy. Rebel Without a Cause is iconic, and that’s because it still feels relevant decades later.
Boyz N the Hood
Telling the story of three teenage friends growing up in Compton in the 1990s, Boyz N the Hood was hailed as an important cultural document upon its release. The movie’s unflinching chronicle of how cycles of anger and violence are created and enforced by a system designed to oppress Black people still resonates today. What’s even more striking, though, is how moving and evocative every single scene is, creating an image of criminals who were almost forced into the world they now live.
West Side Story (2021)
Both versions of West Side Story are worthy of this list, but if you’ve got to pick only one, Steven Spielberg’s more recent adaptation deserves the spot. Revitalizing its source material while paying loving homage to its predecessor, West Side Story is filled with uniformly excellent performances, some truly stunning choreography, and all of those wonderful songs. It’s an emotionally violent film, and brutal because it underlines how preventable every beat of the story was.
A Clockwork Orange
A meditation on free will that’s also a reminder of how annoying teenagers can be, A Clockwork Orange starts as a story about a group of young rebels who are truly terrible, and eventually morphs into a story about compliance and the price we pay when we insist that everyone toe the line. Director Stanley Kubrick was a master filmmaker, and A Clockwork Orange is no exception in his filmography. Coming immediately after 2001, it was proof that he was an unparalleled visionary.
Brick
Director Rian Johnson’s debut feature offered a glimpse at how his career would evolve. The film stars Joseph Gorden Levitt as a teenager who discovers that his ex-girlfriend has been murdered, and becomes determined to find out who did it. It’s a noir that is both silly and deadly serious, and Johnson’s skill is that those tones don’t feel in conflict with one another. Brick is a marvelous debut, and it’s also a movie about the dark underbelly of the cliques that define teenage life.
The Outsiders
Adapted from a totemic novel of the same name, Francis Ford Coppola’s The Outsiders had a lot to live up to, and it managed to do exactly that. Set in the 1950s, the film tells the story of a group of outcasts who wind up killing a member of a rival gang, and are then forced to go into hiding as a result. The movie’s genius is in the way it reckons with the violence of these kids, even as it is more than willing to acknowledge the fact that these boys are young and foolish.
Heathers
One of the most effective satires in the history of the genre, Heathers is a movie about falling in love with a hot bad boy who also happens to be a murderer. The film follows Winona Ryder’s Veronica as she is forced to reckon with her own impulse to destroy the popular image that she has built for herself, and with the violence she provokes in Christian Slater’s J.D. Heathers is devilishly funny, and while it is undeniably violent, it’s a send-up of teens who are a little bit too self-obsessed, however that may manifest.
Menace II Society
A movie that understandably earned comparisons to Boyz N the Hood, Menace tells the story of a young man trying to escape the cycles of gang violence that have defined his life. What makes the movie so great, though, is that it seems to understand that escape may be an admirable goal, but it’s also close to impossible. Like Boyz before it, Menace II Society is really about all of the systems that keep young Black men hemmed in.
City of God
Set against the incredible poverty of Brazil, City of God tells the story of two teenage boys whose lives take different paths. One becomes a photographer and begins to document the drug trade in Rio de Janeiro. The other becomes a drug lord, and begins to take advantage of his friend’s photographs to improve his own reputation. City of God is often pretty funny, but the movie is also filled with tragedy and violence, a reminder of how personal choices intersect with domineering systems.
The 400 Blows
Widely regarded as one of the best films ever made, Francois Truffaut’s The 400 Blows tells the story of a boy who finds himself surrounded by largely indifferent authority figures. Although he plans for a better life, those plans ultimately go awry after one of his petty crimes goes wrong and he catches the attention of Paris police. The 400 Blows was at the forefront of a genre dedicated to honesty about the plights of regular people, and it remains one of the best examples from the genre.