20 best movies like Cruel Intentions (1999)

A controversial portrayal of teens in New York City which exposes a deeply disturbing world of sex and substance abuse. The film focuses on a sexually reckless, freckle-faced boy named Telly, whose goal is to have sex with as many different girls as he can. When Jenny, a girl who has had sex only once, tests positive for HIV, she knows she contracted the disease from Telly. When Jenny discovers that Telly's idea of "safe sex" is to only have sex with virgins, and is continuing to pass the disease onto other unsuspecting girls, Jenny makes it her business to try to stop him.

Mark wants to lose his virginity, but his girlfriend wants to wait. Unfortunately for both of them, a 400-year-old vampire Countess needs to turn a virgin into a vampire before Halloween in order to preserve her own youthful appearance, and when she finds Mark, she turns his life upside-down.

Two New York City girls make a pact to lose their virginity during their first summer out of high school. When they both fall for the same street artist, the friends find their connection tested for the first time.

Malcolm is carefully surviving life in a tough neighborhood in Los Angeles while juggling college applications, academic interviews, and the SAT. A chance invitation to an underground party leads him into an adventure that could allow him to go from being a geek, to being dope, to ultimately being himself.

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

In Barrow, Alaska, teenagers Qalli and Aivaaq find their bond tested when a seal-hunting trip goes wrong, resulting in the death of their friend.

A young woman grieving the loss of her mother, a famous scream queen from the 1980s, finds herself pulled into the world of her mom's most famous movie. Reunited, the women must fight off the film's maniacal killer.

When Danielle is banished to special education because of her misbehavior, she joins Clarke on a road trip to discover themselves.

Minnie Goetze is a 15-year-old aspiring comic-book artist, coming of age in the haze of the 1970s in San Francisco. Insatiably curious about the world around her, Minnie is a pretty typical teenage girl. Oh, except that she’s sleeping with her mother’s boyfriend.

Isabelle, a 17-year-old student, loses her virginity during a quick holiday romance. When she returns home, she begins a secret life as a prostitute for a year.

A teenage loner pushes his way into the underworld of a high school crime ring to investigate the disappearance of his ex-girlfriend.

After being struck and killed by lightning, a young man recounts the way he blackmailed his fellow classmates into contributing to his literary magazine.

After breaking up with his lover and boss, a smooth-talking man takes his teenaged nephew out on the town in search of sex.

A vending machine robbery by small time thief and drug addict Bobbie (Vincent Kartheiser) goes badly awry, and his friends contact street-wise thief and part-time druggie Mel (James Woods) to patch him up.Recognizing a kindred spirit, Mel befriends Bobbie and his girlfriend Rosie (Natasha Gregson Wagner), inviting them to join him and his long-suffering girlfriend Sid (Melanie Griffith) on a drug robbery which should set them up for life. The seemingly simple robbery is a great success, but the sale of the drugs afterward fails badly, and Mel and Bobbie are shot.The four take refuge with the Reverend, who charges them half of their haul from the robbery to care for them. In a desperate attempt to recover their losses, Mel involves the crew in a disastrous, ill-advised jewellery robbery, and they become caught up in a web of violence that rapidly spirals out of control.

Greg is coasting through senior year of high school as anonymously as possible, avoiding social interactions like the plague while secretly making spirited, bizarre films with Earl, his only friend. But both his anonymity and friendship threaten to unravel when his mother forces him to befriend a classmate with leukemia.

A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.

Seen-it-all New York detective Frank Keller is unsettled - he has done twenty years on the force and could retire, and he hasn't come to terms with his wife leaving him for a colleague. Joining up with an officer from another part of town to investigate a series of murders linked by the lonely hearts columns he finds he is getting seriously and possibly dangerously involved with Helen, one of the main suspects.

Biarritz. Sixteen-year-old George, the high school hottie, falls in love with Alex. To get his attention, she initiates a group game with Alex, Nikita, Laetitia and Gabriel. They will discover, test, and push the limits of their sexuality.

High school student Wendy has an odd relationship with her five friends: They're openly sexual with each other, swapping partners every week. But this is all thrown into turmoil when she meets Sean, a new student in school who has a crush on her. Wendy wants to be with Sean, but doesn't want to disappoint her friends, whom she has known since grade school. When she does decide to leave them, her best friend, Billie, threatens revenge.

As a fan of Albert Camus and Jean-Luc Godard, teenage Nick Twisp is definitely out of his element when his mother and her boyfriend move the family to a trailer park. When a pretty neighbor named Sheeni plays records by French crooners, it's love at first sight for frustrated and inexperienced Nick. Learning that she is dating someone, Nick launches a hilarious quest to find his way into Sheeni's heart -- and bed.

An aimless teenager on the outer edges of Brooklyn struggles to escape his bleak home life and navigate questions of self-identity, as he balances his time between his delinquent friends, a potential new girlfriend, and older men he meets online.

A woman and her son must leave a small South Carolina town because of her wild behavior.

Rebellious, quick-witted Erica Vandross is a 17-year-old firecracker living with her single mom, Laurie, and her mom's new boyfriend, Bob, in L.A.'s San Fernando Valley. When Bob's mentally unbalanced son, Luke, arrives from rehab to live with the family, Erica finds her domestic and personal life overwhelmed. With Luke and her sidekicks Kala and Claudine in tow, Erica acts out by exposing a high school teacher's dark secret.

Two 15-year old girls from different sides of the tracks compete to see who will be first to lose their virginity while at camp.

Billy is the self-designated leader of a group of teenagers living in a shelter. Jacob and Rae, Billy's oldest childhood friends, live there as well as part of "the family". Billy has an AIDs-like virus, which he has passed on to his blood brother Jacob. Billy and Rae are boyfriend and girlfriend, much to the dismay of Jacob who has always loved Rae from afar. Billy's philosophy of life, and how that interfaces with having a deadly virus, comes to a head when Billy and Jacob compete in a very unique game of "Tag", with the future of Rae and "the family" dependent upon the outcome.

The teenager and skateboarder Alex is interviewed by Detective Richard Lu that is investigating the death of a security guard in the rail yards severed by a train who was apparently hit by a skate board. While dealing with the separation process of his parents and the sexual heat of his virgin girlfriend Jennifer, Alex writes his last experiences in Paranoid Park with his new acquaintances and how the guard was killed, trying to relieve his feeling of guilty from his conscience.

A teenage boy is sent to a juvenile reform facility in the wilderness. As we learn about the tragic events that sent him there, his struggle becomes one for survival with the inmates, counselors, and the retired war colonel in charge.

Olive, an average high school student, sees her below-the-radar existence turn around overnight once she decides to use the school's gossip grapevine to advance her social standing. Now her classmates are turning against her and the school board is becoming concerned, including her favorite teacher and the distracted guidance counselor. With the support of her hilariously idiosyncratic parents and a little help from a long-time crush, Olive attempts to take on her notorious new identity and crush the rumor mill once and for all.

Despite the tumor-shrinking medical miracle that has bought her a few years, Hazel has never been anything but terminal, her final chapter inscribed upon diagnosis. But when a patient named Augustus Waters suddenly appears at Cancer Kid Support Group, Hazel's story is about to be completely rewritten.

Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his disposal he quickly decides he has been good for too long and it is time to enjoy himself. After an unfortunate incident with the Porsche Joel must raise some cash, in a risky way.

Natalie allows her classmate Jeff, who ran away from home after a fight with his stepfather, to stay at her place while her father is away on a business trip. Natalie soon starts dating Jeff's friend James Casey, who isn't as faithful as she thinks, while her best friend Polly falls in love with baseball player Zoo Knudsen.

Tommy and his older brother Eric live in the midst of vast remote forests. The death of their friend pushes them close to the edge. Eric doesn’t know how to channel his energy. All at once, nature’s vastness feels stifling.

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

A teenager overcomes odds to run a 4-minute mile race.

After Davey's father is killed in a hold-up, she and her mother and younger brother visit relatives in New Mexico. Here Davey is befriended by a young man who helps her find the strength to carry on and conquer her fears.

Punk-rocker turned suburban mom, Kelly, is nostalgic for a life she can no longer have and uncertain of a future she doesn’t yet fit in. Seventeen-year-old Cal is frustrated at his lack of control over the hand he's been dealt. When the two strike up an unlikely friendship, it's the perfect spark needed to thrust them both back to life.

A man with the ability to enter peoples' memories takes on the case of a brilliant, troubled sixteen-year-old girl to determine whether she is a sociopath or a victim of trauma.

An investigation into one woman’s memory as she‘s forced to re-examine her first sexual relationship and the stories we tell ourselves in order to survive.

Former prom king and college freshman Scott returns home for Thanksgiving break and gets dumped by his long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori, an ugly duckling who blossomed in her first semester of college, and they embark on an outrageous adventure through their hometown. But when Scott and Tori start falling in love, they realize that a few months away may have changed them more than they realized.

The most famous Museum in Vienna appears in the film as a mysterious intersection where the characters explore their own lives, the city and how art reflects the world.

After "hooking up" with a series of guys at a house party, April is the talk of her high school.

19-year-old Billy Lynn is brought home for a victory tour after a harrowing Iraq battle. Through flashbacks the film shows what really happened to his squad - contrasting the realities of war with America's perceptions.

A 14 year old genius gets rejected by Harvard and ends up at a much lower ranked school where he makes friends with a mature student.

Two teenage outsiders are demoralized daily at school, until an idea for vengeance offers them a terrifying release.

Lorenzo is a teenager who lives in Patagonia. One day his family receives in his house to Caíto, the son of some friends who are going through a serious family situation and can not take care of him. He is a complicated kid and has difficulty adapting to the new home. Despite the differences, a unique friendship arises between them. Each has much to learn from the other. Caito, still with his things, has that share of rebellion that Lorenzo needs to break the strict molds in his head and to let his most repressed instincts and passions flow. Home life becomes chaotic but vital and engaging. Caíto is much more than a troublesome boy: he is someone who forces Lorenzo's parents to reopen a dark chapter of their past that they would rather not remember.

Four guys, one camera, and their experience chronicling the exhilarating and terrifying rite of passage: losing your virginity. As these guys help their buddy get laid, they'll have to survive friends with benefits, Internet hookups, even porn stars during an adventure that proves why you will always remember your first time.

A sweeping multigenerational story set against the backdrop of the raw, roaring New York City of the late 1980s; adoption, teen pregnancy, drugs, hardcore punk rock, the unbridled optimism and reckless stupidity of the young—and old—are all major elements in this heart-aching tale of the son of diehard hippies and his strange odyssey through the extremes of late 20th century youth culture.

Coming of age story about two inner city youths, who are left to fend for themselves over the summer after their mothers are taken away by the authorities.

After a heist goes awry, a bank robber spends a night trying to free his brother from Riker's Island prison.

An aging Latin lover gets dumped by his sugar mama and must fend for himself in a harsh world.