Best movies like Stay Cool

Shoulda. Coulda. Woulda.

A unique, carefully handpicked, selection of the best movies like Stay Cool Starring Chevy Chase, Hilary Duff, Max Thieriot, Winona Ryder, and more. If you liked Stay Cool then you may also like: Nearing Grace, Never Been Kissed, Night School, Orange County, Carrie and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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The film centers on a successful author who is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.

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Nearing Grace

Having recently lost his mother, teenager Henry Nearing develops a crush on seductive classmate Grace, who toys with him. Though he has been friends with Merna for a long time, he fails to see her sincere attraction to him, and instead wastes time with the uncaring Grace.

Never Been Kissed

Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.

Night School

Teddy Walker is a successful salesman whose life takes an unexpected turn when he accidentally blows up his place of employment. Forced to attend night school to get his GED, Teddy soon finds himself dealing with a group of misfit students, his former high school nemesis and a feisty teacher who doesn't think he's too bright.

Orange County

Shaun Brumder is a local surfer kid from Orange County who dreams of going to Stanford to become a writer and to get away from his dysfunctional family household. Except Shaun runs into one complication after another, starting when his application is rejected after his dim-witted guidance counselor sends in the wrong form.

Carrie

Carrie White, a shy and troubled teenage girl who is tormented by her high school peers and her fanatically religious mother, begins to use her powers of telekinesis to exact revenge upon them.

Psycho Prom Queen

Following the suspected suicide of her friend and fellow teacher, Julie Taylor is hired to take over the senior math class for the last few weeks of school. It's been a difficult year for Julie and this is a fresh start for her and her teenager daughter Miya. Though Julie hopes that being both the new kid and the new teacher's daughter won't be too hard on Miya, she can't help but worry when her daughter becomes fast friends with the school's resident mean girl, Amy Turner.

Prom

At “Prom,” every couple has a story and no two are exactly alike. As the big dance approaches for Nova Prescott, it’s a battle of wills as she finds herself drawn to the guy who gets in the way of her perfect prom. Fellow seniors Mei and Tyler harbor secrets, while others face all the insecurity and anticipation that surrounds one of high school’s most seminal events.

Pretty in Pink

Andie is an outcast, hanging out either with her older boss, who owns the record store where she works, or her quirky high school classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realize that dating someone from a different social sphere is not easy.

A Teacher

A high school teacher in Austin, Texas takes sexual advantage over one of her students. Her life begins to unravel as the details of the relationship are exposed.

The English Teacher

Teacher Linda Sinclair balances her staid home life with an incredible passion for her subject, but her routine is forever altered when a former star pupil and his unsupportive father reenter her life.

The Girl Next Door

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

Salem's Lot

Author Ben Mears returns to his childhood home of Jerusalem’s Lot in search of inspiration for his next book, only to discover his hometown is being preyed upon by a bloodthirsty vampire.

Prom Night

At a high school senior prom, a masked killer stalks four teenagers who were responsible for the accidental death of a classmate six years prior.

Dedication

A modern love story in which a misanthropic, emotionally complex author of a hit children's book is forced to team with a beautiful illustrator after his best friend and collaborator passes away. As Henry struggles with letting go of the ghosts of love and life, he discovers that sometimes you have to take a gamble at life to find love.

The Perks of Being a Wallflower

Pittsburgh, Pennsylvania, 1991. High school freshman Charlie is a wallflower, always watching life from the sidelines, until two senior students, Sam and her stepbrother Patrick, become his mentors, helping him discover the joys of friendship, music and love.

Dirty Deeds

According to a high school's lore, the "Dirty Deeds" are a daunting list of dares almost no student has ever completed. To win the student body's respect and get noticed by his crush, senior Zach is determined to finish the list in the allotted 24-hour time period. As the school's bullying jocks try to thwart him at every turn, Zach embarks on a wild journey, highlighted by beer swilling, grand theft auto and the snagging of an ex-homecoming queen's bra.

Grease

Australian good girl Sandy and greaser Danny fell in love over the summer. But when they unexpectedly discover they're now in the same high school, will they be able to rekindle their romance despite their eccentric friends?

Spontaneous

When students in their high school begin inexplicably exploding (literally), seniors Mara and Dylan struggle to survive in a world where each moment may be their last.

Teaching Mrs. Tingle

A bright high-school senior has her impending status as valedictorian jeopardized when her bitter history teacher, Mrs. Tingle, gives her a poor grade on a project. When an attempt to get ahead in Mrs. Tingle's class goes awry, mayhem ensues and friendships, loyalties and trust are tested by the teacher's intricate mind-games.

Tamara Drewe

A young newspaper writer returns to her hometown in the English countryside, where her childhood home is being prepped for sale.

Superbad

Two co-dependent high school seniors are forced to deal with separation anxiety after their plan to stage a booze-soaked party goes awry.

Prom Pact

It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.

Colossal Youth

When his dream girl returns to school a hopeless romantic teen tries to win her heart, until he hits rock bottom and realizes his true love has been there all along.

Some Freaks

A charming romance develops between a boy with one eye and an overweight girl, though when she loses weight after going to college, their relationship is tested in devastating ways they never dreamed would happen.

Speech & Debate

Frustrated by the hypocrisy they see in their parents, teachers, and the entire school board, an unlikely trio set out to find a common truth and make their voices heard as they revive a defunct school club and take on the world.

Prom Wars: Love Is a Battlefield

Two rival boys-only private schools end up competing for prom dates from a nearby all-girls private school. Caught in the middle is a scholarship student, Percy, at the more cerebral academy of the two. He had been dating Diana, but haughty silver-spoon student Geoffrey at the elite school of the well-off derailed them. So Diana came up with this plan as a way to make the immature boys both pay penance for their classless behavior and to have them actually earn their dates instead of merely expecting them. Which school will win the war? What if the faculties find out? How crazy will things get as the competition heats up?

3 Times a Charm

Emma, the studious editor of the school paper, is tempted by the most popular boy in school, Chris Duval, to cheat. She is given a magical necklace that will give her 3 chances.

Mac & Devin Go to High School

A comedy that follows two high school students -- one overachiever struggling to write his valedictorian speech, the other a senior now going on his 15th year of school.

Senior Year

A thirty-seven-year-old woman wakes up from a twenty-year coma and returns to the high school where she was once a popular cheerleader to finish her senior year and become prom queen.

College

A wild weekend is in store for three high school seniors who visit a local college campus as prospective freshmen.

The Good Student

When Ally, a popular teen and local celebrity goes missing, her small suburban town erupts in panic.

Prom Night in Mississippi

A high school in a small-town in Mississippi prepares for its first integrated senior prom.

Date and Switch

Two guys who make a pact to lose their virginity before prom find their friendship tested when one of them comes out of the closet.

Last Night in Rozzie

When a New York lawyer returns to his Boston hometown to reunite his dying friend with his young son, he is forced to finally confront a childhood trauma.

Jasmine Is a Star

A determined 16-year-old with albinism makes it her mission to become a professional model in her hometown of Minneapolis, while attempting to go unnoticed in every other aspect of her teenage life.

Welcome To Unity

In a sleepy mountain town nestled in rural America, seven foreign exchange students set out to tackle the 'American Dream'.

Aurélie Laflamme: Les pieds sur terre

Aurélie Laflamme is in fifth grade and is preparing for her prom, which she imagines will be wonderful. Surrounded by her best friend Kat, her lover Nicolas Dubuc and her best friend Tommy Durocher, Aurélie will have to face heartbreaking choices about her future and who she really wants to be. An uncompromising professor will come to confront her in her academic and professional choices. MEANWHILE, her mother, who now has a new lover, seems distant and emotional. Aurélie will have to try to understand and find a place for herself in this world which sometimes seems thankless to her.

Senior Year

One of the most widely seen youth films of the late 70's, this dramatic motion picture follows the life of Steve and Angie during their senior year of high school. They each try to live for Christ and reach out to others around them. But, as they deal with their own struggles to share the Lord, a fellow classmate makes things very difficult for them.

The Club

Time stops at midnight at the Senior Prom for five students, one murderous counselor, and John. They must find the courage to face themselves or, when time starts again, they may find that they are joining John's Club. All you have to do is commit murder... or suicide.

Christmas Crush

Twenty-eight-year-old Georgia is convinced the man of her dreams is "the one that got away" back in high school. When Georgia learns of her high school reunion a week before Christmas, she's ecstatic to finally have her chance to win Craig back. But as she gets to relive high school for a night, she begins to realize it might not be Craig at all who got away, but Ben, an old friend with whom she'd fallen out of touch.

A Champion's Fight

Julie Ellis is deeply involved with her high school sweetheart, Luke, even though her parents object that she has made a commitment at such a young age. That commitment only deepens when Luke becomes ill. Wanting to stay close to Luke and offer him comfort, Julie defies her parents' wishes to go away to a prominent school.

Prom Ride

It's the end of the school year for a group of high school friends. Their senior prom was to be a night of elegance, rejoicing and celebrating, but when a psychotic killer hijacks their stretch limo, he is determined to have them Dead On Arrival. The teens are tortured while being held hostage, and soon turn on each other for survival. By the end, we learn that one of the teens had been keeping a secret that played a bigger role in their demise.

Date with Love

When a boy’s video to a female star goes viral, it scores him a date with his celebrity crush to the prom. Complications arise when the famous starlet falls for the boy’s small-town teacher.

A Kismet Christmas

Sarah is a children’s book author who returns to her hometown, where she reconnects with her family and Travis, her teenage crush. She soon discovers that a long-held family legend might actually be true.

Cotton Candy

An uncool high-schooler forms his own group to beat the local hotshots in a battle of the bands.

The Christmas Cure

A doctor returns home for Christmas to find that her father has decided to retire from his own practice. After reuniting with her high school sweetheart, she wonders if she should stay and take over her father's practice.

A Joyous Christmas

Just before Christmas, bestselling author Rachel Kennedy returns to her hometown to host an event for her upcoming book. Though being home is difficult since losing her parents and losing touch with her brother, David, she finds strength from unexpected sources, namely her local producer, Jack and a selfless stranger, Joy. Jack and Joy help Rachel connect with the community, reunite with her brother and reevaluate her motivational message. Rachel and Jack develop an undeniable bond, but Rachel is torn between their relationship and career pressure from her manager, Stuart. As the event approaches, Joy reveals a secret from her past that has a lasting impact on Jack, and Rachel must find a message that brings her fans — and herself – lasting joy.

Denied

Troy, a recent high school graduate, is in love with his best friend Merrick, but Merrick isn't willing to be in a relationship with him. Troy is forced to deal with Merrick's selfishness, his own aching heart, and his unfulfilling life.

Love's Second Chance

When Rose, a passionate fashion stylist in her 30's living in New York, inherits her grandmother's vintage dress shop, she returns to her small hometown to take care of the store. As she's contemplating closing the store for good, she runs into her charming high school crush, Cole Murphy, who convinces her to restore the store and help people in need that can't afford new clothes. After hesitantly agreeing, the two friends reminisce about their old feelings, and realize that the store is not the only that deserves a second chance, but so does their love.

Hearts Under the Olive Tree

When a world-renowned author can’t find inspiration for her next fantasy book, her over-bearing mother takes her to a farmland retreat to get her creative juices flowing, but what she finds is even more magical…

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