If you loved the witty humor, heartfelt friendships, and coming-of-age chaos of 'Booksmart' (2019), you're in for a treat! This article highlights 10 movies and TV shows that capture the same rebellious spirit, sharp dialogue, and unforgettable characters. Whether you're craving more female-led comedies, high school antics, or stories about self-discovery, these picks will keep you entertained and emotionally invested.

Ferris Bueller's Day Off (1986)
Description: Like 'Booksmart', this classic follows clever students bending the rules for one unforgettable day. Both celebrate youthful rebellion and the importance of living in the moment. The charismatic leads and mix of slapstick with smarter humor create a similar tone.
Fact: Matthew Broderick was only 23 when he played the high schooler. The famous parade scene was shot without permits. John Hughes wrote the script in less than a week.


Clueless (1995)
Description: This iconic teen comedy shares 'Booksmart's' sharp wit and socially observant humor. Both feature privileged but intelligent female protagonists navigating high school hierarchies. The films similarly balance satire with genuine heart and character growth.
Fact: The film is loosely based on Jane Austen's 'Emma'. Alicia Silverstone had to wear a corset to achieve Cher's tiny waist. The 'Rollin' with the Homies' line was improvised.


10 Things I Hate About You (1999)
Description: Like 'Booksmart', this Shakespeare adaptation features strong-willed, intelligent female characters and witty dialogue. Both films balance romantic comedy elements with deeper themes of individuality and female agency. The ensemble cast dynamics and high school setting are also similar.
Fact: Heath Ledger's singing in the stadium scene was completely improvised. The film is based on 'The Taming of the Shrew'. Julia Stiles did all her own soccer stunts.


Superbad (2007)
Description: Like 'Booksmart', 'Superbad' is a coming-of-age comedy that follows high school students on a wild night of misadventures before graduation. Both films explore themes of friendship, self-discovery, and the pressures of adolescence with a mix of humor and heart. The fast-paced, witty dialogue and raunchy yet heartfelt tone are also similar.
Fact: Jonah Hill and Michael Cera improvised many of their lines. Seth Rogen and Evan Goldberg wrote the first draft when they were just 13 years old. The film was originally supposed to be animated.


Easy A (2010)
Description: Like 'Booksmart', 'Easy A' features a whip-smart female protagonist navigating high school social hierarchies with humor and intelligence. Both films subvert teen movie tropes while celebrating female friendship and sexual agency. The witty dialogue and self-aware narration style are also comparable.
Fact: Emma Stone ad-libbed many of Olive's sarcastic lines. The film is loosely based on 'The Scarlet Letter'. Penn Badgley's casting was a nod to his 'Gossip Girl' role as another character privy to secrets.


The To Do List (2013)
Description: This comedy shares 'Booksmart's' frank, humorous approach to teenage sexual exploration and female friendship. Both feature overachieving female protagonists learning to balance academic ambitions with personal growth. The 90s setting provides a nostalgic counterpart to 'Booksmart's contemporary vibe.
Fact: Aubrey Plaza performed her own diving stunts. The film was inspired by writer/director Maggie Carey's own experiences. Bill Hader and Carey are married in real life.


The Edge of Seventeen (2016)
Description: This film shares 'Booksmart's' sharp, authentic portrayal of teenage angst and the complexities of high school life. Both feature strong, intelligent female protagonists navigating friendships, family issues, and romantic entanglements with humor and emotional depth. The films balance comedy with poignant moments in a similar way.
Fact: Hailee Steinfeld received a Golden Globe nomination for her performance. Writer/director Kelly Fremon Craig spent months interviewing teenagers to make the dialogue authentic. Woody Harrelson's character was originally written as much more serious before he brought his comedic touch to the role.


Blockers (2018)
Description: This comedy shares 'Booksmart's' progressive take on teenage sexuality and gender roles, flipping traditional teen movie conventions. Both films follow high school friends on a wild night of misadventures, blending raunchy humor with genuine emotional moments. The ensemble cast dynamics are similarly well-developed.
Fact: The film was originally titled 'Cherry Bomb'. Director Kay Cannon is best known for writing the 'Pitch Perfect' films. Geraldine Viswanathan's audition tape impressed producers so much they created a new character for her.


Dope (2015)
Description: Like 'Booksmart', 'Dope' follows academically gifted outsiders navigating the social minefield of high school. Both films blend comedy with social commentary and feature protagonists who challenge stereotypes. The vibrant visual style and hip soundtrack are also points of similarity.
Fact: Pharrell Williams was a producer and contributed to the soundtrack. The film premiered at Sundance where it was bought for $7 million. Shameik Moore learned to play guitar for his role.


Lady Bird (2017)
Description: Greta Gerwig's directorial debut shares 'Booksmart's' authentic, nuanced portrayal of female adolescence and mother-daughter relationships. Both films capture the bittersweet transition from high school to adulthood with equal parts humor and heart. The strong female friendships and coming-of-age themes are particularly similar.
Fact: Saoirse Ronan practiced speaking with a Sacramento accent by listening to NPR reporters from the area. The film was shot in just 26 days. Timothée Chalamet learned to play guitar for his role.
