9. Kids (1995, Larry Clark)
Co-produced by Gus Van Sant, written by Harmony Korine and directed by Larry Clark, Kids encapsulates the dilemmas of sexually active teenagers during the AIDS epidemic in the mid-90s.
Using real teenage New York City street kids as actors, the film chronicles a day in the life for a group of wild, sexually promiscuous teenagers. Among them, Chloë Sevigny (in her first film performance), Rosario Dawson (also her first film role), Leo Fitzpatrick, and Justin Pierce. Their raunchy encounters with each other lead the film to climax at a rave and sex-filled apartment party.
With its modern theme of unsafe sex amongst poorly educated, poverty-striken teens, the film delves into the issues facing kids in the ninties with a frank, pseudo-documentary style.
10. Breaking the Waves (1996, Lars Von Trier)
Von Trier’s first film in his “Golden Heart” trilogy (along with The Idiots and Dancer in the Dark), this film explores the dark side of absolute devotion while depicting a young religious woman’s powerful first experiences with sex.
In the film, the childlike (and virginal) protagonist, Bess (Emily Watson), is deflowered by her newlywed husband Jan (Stellan Skarsgård). Bess’s approach to sex starts off sheepish as she awkwardly offers herself to Jan in the bathroom during their wedding reception. After becoming familiar with it, she is practically addicted to Jan.
Bess’s devotion to Jan becomes all encompassing, and when he must leave home to resume his work on an offshore oil rig, Bess becomes debilitated. She prays to God (who answers her through her own authoritative voice) to send Jan home soon. The next day, Jan is horribly injured on the job and is sent home paralyzed. She perceives her feelings of desire for Jan as selfish, and believes this is why God injured him.
Once at home and now unable to satisfy his wife sexually, Jan tells Bess that sleeping with other men will help him recover from his injuries. Willing to do anything to help him, Bess reluctantly uses her sexuality to comply with Jan’s wishes in the belief that she will cure him. She obediently begins to have sexual encounters with strangers, much to the disapproval of her strict, patriarchal, Calvinist church and family. Her naïve demeanor and utter loyalty to Jan results in her sacrificing her body to save his life.
11. Lolita (1997, Adrian Lyne)
*Please note that this version was chosen for this list over the Kubrick film because of its explicit depictions of sexuality as well as its loyalty to the novel. Even though Kubrick’s version is unique and masterfully done, due to censorship restrictions it doesn’t fully explore the title character’s sexuality as both the book and this film does.
This 1997 film of the Nabokov novel portrays the classic story with frank and sultry detail as well as with bittersweet romanticism.
Humbert Humbert (Jeremy Irons), a British professor in his forties, comes to a small New England town for a teaching job. Looking for a room and board, he meets Charlotte Haze (Melanie Griffith), a bourgeois widow who is renting a room. Humbert is immediately captivated by Mrs. Haze’s thirteen year old daughter, the sensual, yet childlike Dolores “Lolita” Haze (Dominique Swain).
Lolita becomes Humbert’s all encoumpassing obsession, and after her mother sends her off to sleepaway camp, Humbert decides to marry Mrs. Haze in an effort to stay close to Lolita. In a series of unfortunate events, Humbert becomes the sole caretaker of Lolita and begins a torrid and problematic sexual relationship with his legal daughter.
Although the film is told from Humbert’s prospective, we are given insight into Lolita’s point of view from time to time, seeing her make advances toward Humbert and enjoying their sexual activities together. We are also shown through flashback Humbert’s first sexual experiences as a teenage boy and their influence on his obsession with so-called “nymphets.” First sexual experiences can be powerful ones that can mark people for life.
12. American Beauty (1999, Sam Mendes)
Sam Mendes’ directorial debut features the life of a suburban American family and all the dysfunction that lies behind the white picket fence. Kevin Spacey plays a husband and father approaching a mid-life crisis. His outburst is triggered by his obsessive sexual desire for his teenage daughter’s best friend.
Cynical and sexually frustrated Lester Burnham (Kevin Spacey) works a dead-end office job. His perfectionist wife, Carolyn (Annette Bening) is a real estate agent who desires to achieve more with her career, namely to surpass the “King of Real Estate” (Peter Gallagher) in sales. Their insecure and angsty daughter Jane (Thora Birch) goes through her own inner turmoil as she hangs out with her friend Angela (Mena Suvari), a self absorbed young model/cheerleader.
One night at a school basketball match, Lester becomes infatuated with Angela during a cheerleading performance. His lust for her sparks a desire for his lost youth, so he quits his job, starts smoking weed, and decides to work flipping burgers at a fast food restaurant. All the while, he works to build his physique, with the fantasy of impressing and seducing Angela.
Meanwhile, Jane, disgusted by her father’s actions, begins to become attracted to the new boy next door, a strange yet highly intelligent drug dealer, Ricky (Wes Bentley).
There are various sexual attractions that occur between the various characters, but specifically the relationships between Lester and Angela, as well as Jane and Ricky explore the array of feelings, thoughts, and desires that accompany sexual attraction, particularly in youth.
Lester laments his lost youth and attempts to relive it, with Angela being his primary goal. Angela’s relationship with Jane is somewhat controlling, as she enjoys gloating about her attractiveness and seems to use Jane to feel better about herself. When she catches Lester’s eye, she feels validated.
As Jane struggles with her self consciousness and feelings of isolation, she becomes fascinated by Ricky, who is extremely self confident. As their friendship grows, Jane lets Ricky see her vulnerability. She sleeps with him and lets him film her as she expresses her anger towards her father.
This film, which defies genre, captures not only the inprisonment of suburban family life, but explores the blossoming sexuality, self doubt, and desire for attention that is felt during youth.
13. Fat Girl a.k.a. À ma sœur! (2001, Catherine Breillat)
Breillat’s controversial film about teen sex, body image, and virginity captures the relationship between two sisters; the elder one attractive and eager for a romantic fling, the other a young and curious overweight teen.
The two virginal teenage sisters, thirteen year old Anaïs (Anaïs Reboux) and fifteen year old Elena (Roxanne Mesquida) go on holiday with their parents near an idyllic beach in France. The two discuss sex and the subject of losing one’s virginity: the romantic Elena believes it should be done with someone you love, while the more hardheaded Anaïs says it would be better to do with a nobody, just to get it over with.
While strolling through town, Elena meets a young Italian student and begins a sexual relationship with him, struggling to keep to her standards. As the two sisters share a room and are not allowed to travel alone, Anaïs is forced (and is yet intrigued) to witness Elena’s erotic relationship with the Italian.
The explicit sex sequences as well as the brutal and shocking twist ending give this film its controversy. However, apart from the contentious elements of the film, it deals with the discomfort of coming of age, specifically for the chubby and plain Anaïs.
14. Ken Park (2002, Larry Clark & Edward Lachman)
Another Harmony Korine/Larry Clark collaboration, the film centers on the dysfunctional lives and families of a group of teenagers after the suicide of their mutual friend, Ken Park. Shot with unknown, real life teenagers engaging in sex acts, this film shocked many audiences and critics, but it exposes a side of teenage life not often seen in film.
In a small California city, teenager Ken Park shoots himself at a skate park. The film follows his four friends and their maladjusted home lives. Confronting taboo issues such as statutory rape, incest, autoerotic asphyxiation, and violent behavoir in graphic detail, the film reveals a darker side to youth and experiences with sexuality.
15. The Dreamers (2003, Bernardo Bertolucci)
In Bertolucci’s affectionate tale of youth and sex, an young American man is drawn into the intimate and playful world of two French twins. Brought together by their shared love of cinema and revolution, the three withdraw from reality while living in the twins’ family apartment.
While studying French in a University exchange program in the late 1960s, American Matthew (Michael Pitt) meets eccentric twins Isabelle (Eva Green) and Théo (Louis Garrel). After hitting it off with Matthew, the twins invite him to stay with them while their parents are out of town. The three have fun reciting classic film lines, discussing political theorists, and playing games with sexual consequences.
Isabelle and Théo both seduce Matthew into their childish and intimate realm of filmic escapism and physical exploration.
16. Mysterious Skin (2004, Gregg Araki)
Gregg Araki, known for his work in the New Queer Cinema movement, stylishly directs this story of child molestation/sexual abuse and how it affects two young men as they grow up.
Neil McCormick (Joseph Gordon-Levitt) discovers his sexuality at an early age, and when his handsome pediphiliac baseball coach expresses a sexual interest in him, he enjoys it. After one summer of what Neil sees as a sexual initiation with his coach, he goes on to become a male prostitute at fifteen, to the dismay of his best friends.
Brian Lackey (Brady Corbet), who was also on Neil’s childhood baseball team, recalls an incident of amnesia as an eight year old, and heavily interested in science fiction, believes he was abducted by aliens as a child. Unsettled and eager to get to the bottom of his childhood experiences, Brian searches out Neil to find out what really happened to him.
Araki boldly explores the territory and trauma of childhood sexual abuse and how it affects the emotional and psychological development of young people. In the case of one young man, his experiences motivate him to seek out more sexual interactions with older men, while the other young man experiences dissociative amnesia.
17. Palindromes (2004, Todd Solondz)
Solondz’s highly unusual film takes the viewer on an exploration of identity, sex, and adolescence. The film’s unique style uses a dramatic, yet darkly comic tone. Along with the film’s unconventional tone, the main character of the film is performed by eight different actors that vary in age, race, and gender.
Young teenager Aviva desires to have a baby and has sex with the son of a family friend. She is impregnated and delightfully rejoices, to the dismay of her parents. They take her to a clinic where they force her to undergo an abortion. After the procedure, she is no less motivated to get pregnant, and runs away from home in order to achieve her objective. Along the way, she meets an assortment of bizarre characters who influence her and her naïve goal.
Through the use of the multiple actors playing the protagonist, as well as the unusual story and idiosyncratic tone, Solondz studies an atypical teenager’s first experiences with sex. The shifts in actors seem to be representative of a shifting identity that occurs with growth, as well as an inability or unwillingness to fit into societal expectations.