16. The Place Beyond The Pines (2013)
One of the most polarizing films in recent years is also one of the most misunderstood. Everyone who considers Derek Cianfrance’s Blue Valentine follow-up, The Place Beyond The Pines, a masterpiece is in agreement that it is an imperfect one. Nobody can quite agree with what’s wrong with the film, however, though the most common criticism is that the last part of this three-part story, featuring a couple of delinquent teenage boys, was tacked on and pointless.
The first act stars Ryan Gosling as a motorcycle-riding bank robber who is sympathetically trying to take care of his newborn son. The second act stars Bradley Cooper as the police officer wracked with guilt for killing Gosling during a pursuit, who then gets caught up in a corruption scandal within his unit.
The third act skips ahead many years and features the teenage sons of Gosling and Cooper (great performances by Dane DeHaan and Emory Cohen) meeting each other by chance in high school and colliding when the past comes to light.
If viewed as the epic crime saga everyone thought it was/wanted it to be, the third act is, indeed, tacked on and rather pointless. However, if you view The Place Beyond The Pines as being a thoughtful film about lineage, family, and the sins of the father being passed down generation to generation, the third act makes perfect sense (and it’s the second act corruption subplot that one could hold in contempt for a rockier narrative in the film).
Basically, The Place Beyond the Pines is a film that you have to view through the eyes of a teenager to understand fully. The true victims in this film are the two boys at the film’s end, both carrying the weight of their fathers’ guilt and damage without even knowing it and certainly without asking for it. Their youth is an empty, angry, and lonely one where they are both quite possibly doomed to relive mistakes made years before their lives began… The teenage years don’t get much darker than that.
15. The Outsiders (1983)
Francis Ford Coppola’s visually gorgeous (thanks to cinematographer Stephen H. Burum) adaptation of S.E. Hinton’s classic novel is something of a misunderstood masterpiece of its time. Operatic and melodramatic, Coppola’s grandiose filmmaking style is actually the perfect voice to bring the teenage social class drama to the screen.
Matt Dillon, Patrick Swayze, Tom Cruise, Ralph Macchio, C. Thomas Howell, and Emilio Estevez all deliver hyper-real and (sometimes) over-the-top early performances that perfectly reflect the heightened emotions of their misunderstood teenaged central characters.
14. Election (1999)
Alexander Payne’s high school satire is one of the meanest, cleverest, and most absurd depictions of high school social wars since Heathers. Reese Witherspoon is insanely perfect as the psychotically ambitious high school student who will stop at nothing to win her class presidency.
While silly and darkly comedic in tone, the film also expertly manages to get across some very telling social satire in the process.
13. American Beauty (1999)
Director Sam Mendes’ and screenwriter Alan Ball’s career-starting dark suburban satire is one of the most deserved Best Picture Oscar winners of all time. Kevin Spacey and Annette Benning deliver career-high performances (no small feat for either of them), but it’s the heartbreaking sincerity of the teenage characters and performances that make this film stand out as something great.
Thora Birch and Wes Bentley give a sweetly romantic portrayal of two damaged young lovers, and Mena Suvari gives a sultry but naïve Lolita-esque (on the surface, at least) portrayal of the young object of a very bored and confused middle-aged Spacey’s desires. Painfully honest and darkly hilarious, American Beauty gave us some of the most fearless portrayals of (at the time) modern teenagers ever seen in a major studio release.
12. Lolita (1962)
Stanley Kubrick’s adaptation of Vladmir Nabokov’s infamous pedophilia-themed novel of the same name was enormously risqué for its time. By today’s standards, Lolita is fairly tame, but the audacity alone of such material to be handled in a darkly comedic tone still manages to make you squirm with disbelief in just the right moments (as does James Mason’s comically obsessed performance).
Lolita continues to stand out because it’s title character (played with advanced wisdom by Sue Lyon) is no innocent victim to the events around her. In spite of her young and seemingly innocent age, she’s wholly aware of her powers and is willing to exploit the men chasing after her every bit as much as they are willing to exploit her.
11. Ask Me Anything (2014)
Writer-director Allison Burnett’s film is one of the most (currently) unknown on this list. A teenage girl (Britt Robertson) takes a year off between high school and college to explore life and multiple men, only to relay her exploits in detail to her growing list of blog followers. She’s a young girl, like so many others who have grown up in the online world, who can’t express herself without an audience and who can’t feel anything real without living some enormous lies.
For its first act or so, Ask Me Anything doesn’t particularly hint at darkness. It more envelops you in its lead character’s exuberance, her bad and girly behavior, and presumably sets you up for a film that the seemingly simple teenager’s unformed mentality would enjoy. As it unfolds, however, Ask Me Anything becomes much more aware of itself than it pretended, and the character becomes much more complicated than she seemed.
Robertson’s almost-deceptively layered and highly thought-through performance is very easy to write off as fluff and miss for it’s darker shadings and finer details. She guides us through her character’s escapades and the different depths of her (lack of) identity with skill, precision, and natural charisma. The result is a sadly memorable and tragically lost modern teenage character that comfortably holds its rank with all the undisputed classics on this list.
10. Carrie (1976)
Brian DePalma’s film is the ultimate revenge fantasy for anyone who was ever tortured or tormented in high school. With the film’s high school girl shower room scene opening, Carrie quickly plugs you into the high emotions of teenage humiliation and cruelty. The film that ensues is a nightmarish and operatic depiction of those emotions building and eventually manifesting themselves into anger, rage, and, ultimately, destruction.
At first glance, Carrie is a brilliantly executed horror film about a telekinetic high school girl who wreaks havoc on her prom. What it actually is, however, is one of the most realistic cinematic depictions of the inner emotional violence experienced by every high school outcast.
9. Rebel Without a Cause (1955)
Without a doubt, this film is the grandfather of all dark teenage films. Teenage anger, rebellion, and whining have never been more mysterious or sexy, especially in the pouty display of iconography that is James Deans’ eternally classic performance.
If viewed with today’s eyes, it’s slightly easy to scratch your head over what most the people in the movie are so upset about (everything is just so perfect and pretty and fun, even when they’re sad!). Almost naïve by today’s standards, Rebel Without a Cause is innocent in its anger and precious in its presentation, which makes it all the more important for today’s over-exposed and numb youths to see it.
Perhaps they should experience a world where it actually is unexpected and surprising for young people to be misunderstood and where their mistreatment doesn’t have to reach dizzying heights before somebody reacts.