Movies like Clueless are set in high school or college settings, with a comedic tone, and often focus on the coming of age and teenage angst of the main characters.
They usually have a strong female lead and explore friendship, romance, and growing-up themes.
The film is loosely based on Jane Austen’s 1815 novel Emma, with a modern-day setting of Beverly Hills.
The plot centers around a wealthy and fashionable high school student, Cher Horowitz, who tries to boost the popularity of a new student, Tai Frasier, and along the way, discovers her feelings for Tai’s stepbrother, Josh.
Similarly, several movies like “Clueless” have been released over the years, which have captured the essence of teenage life in a comedic and relatable way.
The following are the best-selected movies, like clueless.
1. The Breakfast Club (1985)
- Director: John Hughes
- Cast: Emilio Estevez, Paul Gleason, Anthony Michael Hall, John Kapelos, Judd Nelson, Molly Ringwald, and Ally Sheedy.
- IMDb Rating: 7.9/10
“The Breakfast Club” is a 1985 American coming-of-age film directed by John Hughes.
The film follows five high school students from different cliques forced to spend a Saturday together in detention.
The five students initially have little in common and begin to open up and share their stories.
Over the day, they realize they all have more in common than they had initially thought.
The film stars Emilio Estevez, Anthony Michael Hall, Judd Nelson, Molly Ringwald, and Ally Sheedy as the five students.
Each character represents a stereotype commonly found in high school: the jock, the nerd, the criminal, the princess, and the outcast.
The film explores themes of identity, conformity, and the pressure of societal expectations. The Breakfast Club is one of the best movies like clueless.
“The Breakfast Club” was a critical and commercial success upon its release, and it has since become a cultural touchstone.
It is considered one of the greatest films of the 1980s, and it is often cited as a quintessential high school film.
The film’s portrayal of teenage life, relatable characters, and honest and heartfelt dialogue have made it a timeless classic that continues to resonate with audiences today.
2. Means Girls (2004)
- Director: Mark Waters
- Cast: Lindsay Lohan, Rachel McAdams, Tina Fey, Amanda Seyfried, Lacey Chabert, and Lizzy Caplan
- IMDb Rating: 7.2/10
Mean Girls is a 2004 American teen comedy film about a high school girl named Cady Heron.
After being homeschooled in Africa, the girl moves to the United States and starts attending a public high school.
She befriends a group of girls known as “the Plastics,” but her newfound popularity comes at a cost as she learns about the harsh realities of high school cliques and politics.
The film explores themes of friendship, social hierarchy, and the adverse effects of popularity and status-seeking.
The film was a commercial and critical success, grossing $129 million worldwide and receiving positive reviews for its humor and performances.
It has since become a cult classic, and its legacy has seen it considered one of the most iconic movies of the 2000s.
3. 10 Things I Hate About You (1999)
- Director: Gil Junger
- Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, and Larisa Oleynik.
- IMDb Rating: 7.2/10
“10 Things I Hate About You” is a 1999 romantic comedy film directed by Gil Junger and starring Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt.
The film is a modern retelling of William Shakespeare’s play “The Taming of the Shrew.”
The story follows high school student Kat Stratford, known for being difficult and unapproachable, and her younger sister Bianca, famous and well-liked. For Bianca to date, Kat must also be allowed to date.
This movie leads to a scheme in which new student Cameron pays lousy boy Patrick to take Kat out on a date.
Along the way, Kat and Patrick learn valuable lessons about themselves and each other and eventually fall in love.
The movie is a light-hearted comedy, with a bit of romance and comedy, with less emphasis on hate and more on love. This movie is one of the best movies like clueless.
4. Legally Blonde (2001)
- Director: Robert Luketic
- Cast: Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, Jennifer Coolidge, Ali Larter, and Holland Taylor
- IMDb Rating: 6.2/10
“Legally Blonde” is a 2001 American comedy film directed by Robert Luketic and starring Reese Witherspoon.
The film follows the story of Elle Woods, a sorority girl who enrolls in Harvard Law School to win back her ex-boyfriend Warner.
Along the way, she faces challenges and discrimination as a blonde but ultimately proves to be a skilled and dedicated student. Legally Blonde is one of the best movies like clueless.
Throughout the movie, Elle uses her intelligence, creativity, and determination to succeed in her classes and eventually assist in a high-profile murder trial.
Along the way, she also learns to be independent and not to define herself by her relationships.
The movie is a light-hearted comedy with a bit of romance and conveys empowerment and self-discovery.
The film was a commercial success, leading to a sequel, “Legally Blonde 2: Red, White & Blonde” in 2003, and a musical adaptation.
5. Emma (1996)
- Director: Douglas McGrath
- Cast: Gwyneth Paltrow, Jeremy Northam, Toni Collette, Alan Cumming, Ewan McGregor, Sophie Thompson, Juliet Stevenson, and Phyllida Law
- IMDb Rating: 7.2/10
Emma is a 1996 period drama film directed by Douglas McGrath and based on the novel of the same name by Jane Austen.
The film stars Gwyneth Paltrow as Emma Woodhouse, a wealthy and beautiful young woman who lives in the small town of Highbury, England, in the early 19th century.
Emma is known for her wit and intelligence, but she also tends to be arrogant and meddlesome.
She is determined to play matchmaker for her friends and acquaintances, but her attempts often backfire, causing chaos and confusion.
Despite her flaws, Emma is a relatable and likable, and Paltrow’s portrayal of her is widely considered one of the character’s best adaptations. Emma is one of the best movies like clueless.
Emma received positive reviews upon its release, with many praising Paltrow’s performance and the film’s faithful adaptation of the novel.
It was nominated for two Academy Awards, including Best Costume Design.
Overall, Emma is a charming and engaging film that perfectly captures the wit and humor of Jane Austen’s novel. It is a must-watch for book fans and period drama lovers.
6. Never Been Kissed (1999)
- Director: Raja Gosnell
- Cast: Drew Barrymore, Michael Vartan, David Arquette, Molly Shannon, John C. Reilly, Marley Shelton, and Jessica Alba,
- IMDb rating: 6/10
“Never Been Kissed” is a 1999 romantic comedy film directed by Raja Gosnell and starring Drew Barrymore and Michael Vartan.
The film tells the story of Josie Geller, a 25-year-old copy editor who has never been kissed despite her intelligence and professional success.
Her newspaper editor sends Josie undercover as a high school student to report on the teenage experience.
She is tasked with reliving her awkward and painful adolescent years, which she thought she had left behind.
Josie’s journey of reliving her teenage years allows her to understand and accept the person she was and to become the person she wants to be.
The film also explores the idea of being judged by others and the pressure to conform to societal expectations.
“Never Been Kissed” received mixed reviews upon its release but has since become a cult classic and beloved by many.
Overall, “Never Been Kissed” is a heartwarming and entertaining film that explores the struggles and triumphs of growing up and finding oneself.
7. Bring It On (2000)
- Director: Peyton Reed
- Cast: Kirsten Dunst, Eliza Dushku, Jesse Bradford, Gabrielle Union, Clare Kramer, Nicole Bilderback, Joelson, and Brandi Williams
- IMDB Rating: 6.1/10
“Bring It On” is a film that has become a cult classic among audiences since its release in 2000. This movie tells the story of a high school cheerleading squad.
The charismatic and determined Torrance Shipman leads the squad as they navigate the cutthroat world of competitive cheerleading.
The Rancho Carne Toros team has always been the reigning champions in their division.
However, they do discover that their championship routines have been stolen from a rival squad.
The East Compton Clovers stole the championship. Bring it one is one of the best movies like Clueless.
Rancho Carne Toros were forced to scramble to create new routines before the next competition. One of the main themes of the film is the idea of cultural appropriation.
However, the Toros are forced to confront the fact that they have been benefitting from the hard work and talent of the Clovers without giving them credit.
The film also explores themes of friendship, teamwork, and determination.
“Bring It On” was a commercial success and received positive reviews from critics.
The film’s catchy cheer routines, stage musical adaptation, and relatable teenage characters helped it to gain a cult following.
8. Can hardly Wait (1998)
- Directors: Harry Elfont and Deborah Kaplan
- Cast: Jennifer Love Hewitt, Ethan Embry, Charlie Korsmo, Lauren Ambrose, Peter Facinelli, and Seth Green.
- IMDb Rating: 6.6/10
“Can Hardly Wait” is a 1998 American teen comedy film that follows a group of high school seniors attending their graduation party and navigating the ups and downs of their relationships and emotions.
The main character, Preston Meyers, is a shy and nerdy student who has a crush on the famous and beautiful Amanda Beckett.
As the night goes on, Preston attempts to confess his feelings to Amanda while also dealing with his insecurities and the drama of his classmates.
Along the way, the film also features a cast of supporting characters, including jocks, nerdy outcasts, and partying seniors, all with their own stories and experiences.
The film ends with the graduation party winding down and the characters facing the reality of growing up and moving on.
9. Heathers (1989)
- Director: Michael Lehmann
- Cast: Winona Ryder, Christian Slater, Shannen Doherty, Lisanne Falk, Kim Walker, Penelope Milford, and Lance Fenton
- IMDb Rating: 7.3/10
Heathers is a 1989 dark comedy film that explores the dark side of high school life and the dangerous consequences of seeking power and popularity.
The film stars Winona Ryder as Veronica Sawyer, a high school student of the popular clique, the Heathers.
The group comprises three girls, all named Heather, who dominate the social scene at Westerberg High School. Heathers is one of the best movies like clueless.
Veronica’s life takes a dramatic turn when she meets J.D. (Christian Slater), a new student different from anyone she’s ever met. J.D. is charismatic and mysterious and quickly becomes Veronica’s love interest.
However, J.D. has a dark side, and he soon reveals that he wants to rid the school of the popular clique, the Heathers. J.D. and Veronica embark on a dangerous and violent journey to eliminate the Heathers and take control of the school’s social hierarchy.
Along the way, they encounter various obstacles and challenges, including the school’s principal and the police.
The film explores themes of social hierarchy, power, and the consequences of violence.
10. Pretty In Pink (1986)
- Director: Howard Deutch
- Cast: Molly Ringwald, Andrew McCarthy, Jon Cryer, Harry Dean Stanton, Annie Potts, James Spader, Andrew Dice Clay, and Kate Vernon
- IMDb Rating: 7.1/10
Pretty in Pink is a 1986 American romantic comedy film directed by Howard Deutch and written by John Hughes.
The movie follows up a high school girl named Andie who is torn between her feelings for two very different boys.
One of the boys came from a wealthy family, and the other from a working-class background. Pretty in Pink is one of the best movies like clueless.
One of the most iconic elements of the film is its fashion, with Andie’s eclectic, punk-inspired wardrobe becoming a defining aspect of her character.
The film’s title song, “Pretty in Pink,” was performed by The Psychedelic Furs, and the film’s soundtrack was popular among the audiences.
Pretty in Pink also dealt with class and social status themes, which were prevalent in the 1980s, and explored the complexities of teenage romance and growing up.
It also starred James Spader, Harry Dean Stanton, and Andrew Dice Clay in supporting roles.
Overall, Pretty in Pink is a beloved and enduring film that continues to resonate with audiences of all ages.
It is a nostalgic trip back to the 1980s and a timeless story of first love and self-discovery.
11. She’s All That (1999)
- Director: Robert Iscove
- Cast: Freddie Prinze Jr, Rachael Leigh Cook, Matthew Lillard, Kieran Culkin, Anna Paquin, and Gabrielle Union
- IMDb Rating: 6.1/10
She’s All That is a 1999 American teen romantic comedy film that follows Zack Siler, a popular high school student challenged by his best friend, Dean.
Zack was challenged to turn the school’s “ugly duckling,” Laney Boggs, into a prom queen.
As Zack and Laney spend more time together, they develop feelings for each other.
Afterward, they must navigate the challenges of their social status and the expectations of their peers.
She’s All That was a commercial success upon its release, grossing over $103 million at the box office.
It received mixed reviews from critics but was praised for its performances and modern take on the Pygmalion story.
The film’s soundtrack was also popular among the audiences and featured songs from artists such as Sixpence None the Richer, Fatboy Slim, and K.D Lang. She’s all that is one of the best movies like clueless.
Overall, She’s All That is a fun and entertaining film that has become a cult classic in the teen romantic comedy genre.
It is a nostalgic trip back to the late 1990s and a timeless story of first love and self-discovery.
12. Easy A (2010)
- Director: Will Gluck
- Cast: Amanda Bynes, Penn Badgley, Dan Byrd, Thomas Haden Church, Patricia Clarkson, and Stanley Tucci.
- IMDB Rating: 7.1/10
Easy A is a 2010 American teen comedy-drama film that is a modern retelling of Nathaniel Hawthorne’s classic novel The Scarlet Letter, set in a high school setting.
The film follows Olive Penderghast, a high school student falsely accused of promiscuity by her classmates.
To clear her name, she embraces the rumors and wears a red “A” on her clothing, similar to the protagonist of The Scarlet Letter.
Along the way, she learns valuable lessons about identity, friendship, and the power of perception. Easy A is one of the best movies like clueless.
Easy A received positive reviews from critics for its clever writing, relatable characters, and Emma Stone’s performance as Olive.
The film also had a successful box office run, grossing over $75 million worldwide.
Despite its comedic tone, the film also addresses essential themes such as bullying, gender stereotypes, and the pressure of societal expectations.
Easy A is a clever and entertaining film that will resonate with teens and adults alike.
13. Footloose (1984)
- Director: Herbert Ross
- Cast: Kevin Bacon, Lori Singer, John Lithgow, Dianne Wiest, Chris Penn, Sarah Jessica Parker, and John Laughlin
- IMDb Rating: 6.8/10
“Footloose” is a 1984 American musical drama film that tells the story of a teenager named Ren McCormack.
He moves to a small town where the local minister has banned dancing and rock music.
Ren teams up with the minister’s daughter Ariel and other teens in the town to change the rules and bring dancing back to their village.
The film’s title song, “Footloose,” was a hit for Kenny Loggins, and the film’s soundtrack was a commercial success.
A stage musical adaptation of the film was also created, premiering in 1998. The musical has been performed in many countries worldwide and adapted into a movie in 2011.
14. The Half of It (2020)
- Director: Alice Wu
- Cast: Leah Lewis, Daniel Diemer, Alexxis Lemire, Collin Chou, Becky Ann Baker, Wolfgang Novogratz, Catherine Curtin, and Enrique Murciano
- IMDb Rating: 7.4/10
“The Half of It” is a 2020 American coming-of-age romantic comedy film directed by Alice Wu.
The film follows Ellie Chu, a shy, straight-A student who moonlights as a ghostwriter for her classmates’ love letters.
When popular jock Paul Munsky asks Ellie to help him win the heart of his crush, Aster Flores, Ellie agrees.
Surprisingly, Ellie starts to fall for Aster herself. She must navigate her feelings while trying to help Paul win over the girl they both love.
The film explores identity, sexuality, and the complexities of love and friendship.
This movie was criticized for its witty writing, relatable characters, and nuanced portrayal of its LGBTQ+ characters. Half of it is one of the best movies, like clueless.
15. The Edge of Seventeen (2016)
- Director: Kelly Fremon Craig
- Cast: Hailee Steinfeld, Woody Harrelson, Kyra Sedgwick, Haley Lu Richardson, Blake Jenner, Hayden Szeto, and Alexander Calvert
- IMDb Rating: 7.2/10
“The Edge of Seventeen” is a coming-of-age comedy-drama exploring struggles.
It also explores the triumphs of adolescence through the eyes of its protagonist, Nadine.
The story tells of a high school junior struggling to navigate teenage life’s challenges, including friendships, family dynamics, and romantic relationships. This film is one of the best movies like clueless.
Nadine, played by Hailee Steinfeld, is a loner who has always struggled to fit in with her peers.
She is fiercely independent and has a sharp wit, but her social awkwardness and tendency to speak her mind often land her in trouble.
She is also dealing with the recent death of her father, which has left her feeling lost and alone.
The film takes an honest and unflinching look at the complexities of teenage life, capturing the ups and downs of growing up in a relatable and authentic way.
Nadine’s struggles with self-doubt, identity, and relationships are portrayed with a realism that is both raw and relatable.
One of the standout performances in the film is that of Woody Harrelson, who plays Nadine’s history teacher and mentor.
His character, Mr. Bruner, serves as a sounding board for Nadine and offers a wise perspective on life and growing up.
Their scenes are some of the film’s most influential and emotional moments.
