Teen movies are a staple of the Millennial and Generation Z eras. The late-90s through the early-2000s brought a slew of films telling stories revolving around themes that are particularly relevant to teenagers, preteens, or young adults, such as coming of age, trying to fit in, bullying, peer pressure, first love, teen rebellion, conflict with parents, and angst or alienation. Bringing these teen-relevant issues to light was a great way to get a younger generation to talk about their problems.

Some of the best teen films, in fact, were comedies. They told these stories and taught relevant life lessons with the most hilarious undertone or comedic actors. The teen comedy genre was mostly nonexistent in the first three decades of programming. Still, it developed into what it is now thanks to the emergence of networks and studios that specialized in producing material for children and teenagers. The top comedic teen films from the 2000s are listed below.

9 Napoleon Dynamite

     Fox Searchlight Pictures

Starring Jon Heder as the title character Napoleon, the 2004 movie Napoleon Dynamite tells the story of the awkwardness of high school. Napoleon and his new friend Pedro (Efren Ramirez) make a hilarious attempt at running for class president, hoping to change the status quo. Jon Gries portrays Napoleon’s Uncle Rico and lends his comedic talents to the film. Napoleon Dynamite is now considered by many a cult classic. Heder even said in a 2014 interview with Entertainment Weekly that he “couldn’t be more stoked about being this cult character. I grew up loving Coen brothers films and Pee-wee Herman, all those films that get quoted a ton.”

8 Superbad

     Sony Pictures Releasing

Jonah Hill and Michael Cera play Seth and Evan, two teenagers set to graduate from high school, respectively, in the movie Superbad from 2007. The characters want to party and lose their virginity before they graduate, but their plan is more difficult than they anticipated. Seth Rogen and Evan Goldberg wrote the screenplay, which was partially based on their own high school years in the 1990s. The film was so successful it made Rolling Stone’s list of the Top 10 Comedies of the era.

7 Legally Blonde

     MGM Distribution Co.

Legally Blonde is one of the funniest, most quotable films of the 2000s. Starring Reese Witherspoon, Luke Wilson, Selma Blair, Matthew Davis, Victor Garber, and Jennifer Coolidge, the film is based on a 2001 novel of the same name by Amanda Brown. Legally Blonde was nominated for two Golden Globe Awards and an MTV Movie Award. The film’s box office success led to a 2003 sequel, Legally Blonde 2: Red, White & Blonde, and a 2009 direct-to-DVD spin-off, Legally Blondes. Additionally, Legally Blonde: The Musical premiered in 2007. In 2022, it was announced Mindy Kaling was writing the script for Legally Blonde 3, but no release date has been set.

6 John Tucker Must Die

     20th Century Studios

The 2006 teen comedy John Tucker Must Die was helmed by Betty Thomas, renowned for playing Sergeant Lucy Bates on the television series Hill Street Blues, for which she won an Emmy Award. In John Tucker Must Die, three young ladies (Ashanti, Sophia Bush, and Arielle Kebbel) realize that school basketball star John Tucker (Jesse Metcalfe) has been secretly courting each of them and declaring that each is “the one.” As such, they plan to break his heart. They recruit a shy, unpopular girl (Brittany Snow) to carry out their plan to publicly shame him. A hilarious quest ensues, leading many of the characters to realize what is really important to them.

5 The Lizzie McGuire Movie

     Walt Disney Studios

The Lizzie McGuire Movie, released in 2003, was the first theatrical film based on a Disney Channel series. It serves as the conclusion of the same-named television series. The film continues the story of Lizzie McGuire (Hilary Duff), who travels to Rome with her best friends on a trip organized by their school for the summer holiday. Soon after, she meets Paolo Valisari (Yani Gellman), a popular local musician whose duet partner resembles Lizzie nearly perfectly. Lizzie agrees to fill in for the girl at a huge performance and pretend to sing while a recording is played because Paolo and his collaborator recently got into an argument. But she has to rely on her own vocal abilities when things don’t go as planned. In 2019, it was announced a reboot was planned, but according to Duff, Disney was not in agreement over the direction the project should take and it has since been canceled.

4 Bring It On

     Universal Pictures

2000’s Bring It On shows the journey a high school cheerleading team takes as it prepares for the national competition. When newly appointed captain Torrance Shipman (Kirsten Dunst), with the help of new recruit Missy Pantone (Eliza Dushku), learns the previous captain stole all their routines from squads at less fortunate schools, they must come up with something that will wow the judges using their own skills. The film mocks cheerleading, but has substance and a message that everyone should hear: there are things in life more important than winning. Five Bring It On sequels have followed the first film.

3 Freaky Friday

     Walt Disney Pictures 

The 1972 book Freaky Friday by Mary Rodgers served as the inspiration for the 2003 film adaptation of Freaky Friday. A mysterious and mystical Chinese fortune cookie switches the bodies of a mother and daughter (Jamie Lee Curtis and Lindsay Lohan) who are at odds with one another, thinking neither understands the other’s position. Curtis received a Golden Globe nomination for Best Actress in a Motion Picture: Musical or Comedy for the movie. After the 1976 film with Barbara Harris and Jodie Foster, and the 1995 made-for-TV movie with Shelley Long and Gaby Hoffmann, it was Disney’s third film version of the book. Both Lohan and Curtis have recently indicated that they would be interested in starring in Freaky Friday 2.

2 The Princess Diaries

     Walt Disney Pictures

The Princess Diaries is a 2001 comedy about growing up that is partially based on the same-titled 2000 young adult novel by Meg Cabot. Mia Thermopolis (Anne Hathaway), a quiet American teen, is portrayed in the film as the heir-apparent to a European country. Mia must choose whether to take the crown she has inherited or surrender it permanently under the guidance of her estranged grandmother (Julie Andrews), the monarch of the realm.

Hathaway’s emergence as a bankable star and Andrews’ resuscitation of her cinematic career are both attributed to the movie’s popularity. A sequel, The Princess Diaries 2: Royal Engagement, was released in 2004 with similar success. While there have been persistent speculations of a potential third film for years, there has been no official confirmation of it.

1 Mean Girls

     Paramount

The teen comedy Mean Girls, which Mark Waters directed and Tina Fey wrote, was released in 2004. The 2002 non-fiction self-help book Queen Bees and Wannabes by Rosalind Wiseman — which discusses female high school social cliques, bullying at school, and the negative impact these behaviors can have on kids — is a major inspiration for the movie. After years of being homeschooled by her scientist parents, Cady Heron (Lindsay Lohan) finally attends public school when her family relocates to the American suburbs. Unknowingly, Cady finds herself in the good graces of a select group of popular students known as “The Plastics,” but she quickly learns how her shallow group of new friends came to be known by this moniker. A made-for-television sequel, Mean Girls 2, which debuted on ABC Family in 2011, and a musical adaption, which debuted on Broadway in 2018, were both produced as a result of the film’s success.