6. Clueless

On July 19, 1995, Jane Austen’s classic novel Emma was reimagined and released in a Paramount Pictures film titled Clueless. The Amy Heckerling-written and directed film featured Alicia Silverstone as Cher Horowitz, a stylish, popular student in Beverly Hills who decides to play matchmaker while attempting to figure out what she wants for her own life. The film covers dating life, makeovers, hilarious and now-outdated slang, and the struggle of becoming a better person. Other stars include Stacey Dash, Brittany Murphy, and Paul Rudd. Heckerling reflected in a Little White Lies interview saying, “I remember reading ‘Emma’ in college and thought everything in it was so applicable to the things that’d work for a teenage girl.” However, the producers were not keen on creating a big budget film designed for teenage girls. Thankfully, the film continued with producer Scott Rudin, who loved the idea. Since its release, there has been a book series, a Broadway show, and TV series with the same name. 

Clueless can be streamed on Paramount Plus and Hulu.

5. Ferris Bueller’s Day Off

Matthew Broderick famously says as the titular character in Ferris Bueller’s Day Off, “Life moves pretty fast. You don’t stop and look around once in a while, you could miss it.” Written and directed by John Hughes, the teen comedy follows Ferris along with his friend Cameron (portrayed by Alan Ruck) and his girlfriend Sloane (Mia Sara) as they skip school to explore the daytime life of Chicago. Despite the comedic relationships, awkward situations, and witty fourth wall breaks that occur throughout the film, the narration of Ferris’ thoughts throughout the span of the film explore hard philosophical topics for a teenager. Ferris reflects the idea of finding the meaning of life through rebelling against societal expectations. Distributed by Paramount Pictures and released on July 11, 1986, it’s a film that has left audiences happy crying for decades. 

Ferris Bueller’s Day Off can be streamed on Paramount Plus and YouTube.

4. The Perks of Being a Wallflower

There are some films that one will watch as they grow up that will permanently affect them forever. Summit Entertainment’s The Perks of Being a Wallflower is certainly one of those films that teens and young adults should watch at least once as they enter adulthood. Directed and written by Stephen Chbosky and based on his 1997 novel of the same name, the film follows Charlie Kelmeckis (portrayed by Logan Lerman) as he enters high school and struggles to make new friends while battling depression and PTSD. According to a 2012 Complex interview with Chbosky, he wrote the novel based on his and his friends’ experiences and asked, “why do good people let themselves get treated so badly?” to which he answered himself, “We accept the love we think we deserve.” The film delves into topics such as mental health issues, sexuality, rape, and independence. Along with Lerman, the film also stars Emma Watson, Ezra Miller, Paul Rudd, and Nina Dobrev. 

The Perks of Being a Wallflower can be streamed on Prime Video.

3. Mean Girls

After the great successes of Heathers and Clueless, the people needed more teen girl-centered stories. On April 19, 2004, Paramount Pictures released Mean Girls, a teen comedy film directed by Mark Waters (also known for Freaky Friday) and written by Saturday Night Live star Tina Fey based on the self-help book Queen Bees and Wannabes by Rosalind Wiseman. Focused on categorizing the social cliques of the average high school and how damaging they can be, the film follows Cady Heron (portrayed by Lindsay Lohan) as she moves to an American high school and navigates the wilderness that is high school. Despite the warnings from her first two friends, she accepts an invitation to join the “Plastics,” a trio of popular rich girls. The film instantly became a huge success and has led to sequels, musicals, and a swarm of memes that are still used to this day. 

Mean Girls can be streamed on VIX and Paramount+.

2. The Breakfast Club

Written and directed by John Hughes (also known for Sixteen Candles and Home Alone), The Breakfast Club showed that despite the many differences among classmates, high schoolers are all just kids trying to get by in a world that is unfair to them. Released on February 7, 1985, the film followed five students at Shermer High School as they report to an all-day Saturday detention led by the quick-tempered vice principal Richard Vernon (portrayed by Paul Gleason). Assigned with the task to write a thousand-word essay based on who they think they are as people, the five students quickly feel the cabin fever and begin breaking the rules of staying silent and in their seats.

The students are all given nicknames and include: the “princess” Claire Standish (portrayed by Molly Ringwald), the “brain” Brian Johnson (portrayed by Anthony Michael Hall), the “criminal” John Bender (portrayed by Judd Nelson), the “basket case” Allison Reynolds (portrayed by Ally Sheedy), and the “athlete” Andrew Clark (portrayed by Emilio Estevez). As each stereotyped student gets on each other’s nerves, they eventually let loose and begin to open up about their experiences that led them to detention in the first place. The Universal Pictures film demonstrated how teenagers, despite the high expectations put onto them, struggle to find understanding of their place in the world by both them and by the adults who are supposed to guide them. 

The Breakfast Club can be streamed on Netflix.

1. Dead Poets Society

Possibly the most heart-shattering contender on this list, Buena Vista Pictures film Dead Poets Society tells the story of an English teacher by the name of John Keating (portrayed by Robin Williams) as he influences his students’ lives forever. The Peter Weir-directed and Tom Schulman-written film released on June 2, 1989 and has been making people cry bittersweet tears ever since. Keating’s unorthodox methods of teaching poetry in the film inspires his students to restart Keating’s old poetry club. The film then follows as the students learn to make their lives their own in a bubble that pressures them to take a predetermined path. Exciting discoveries are made and tragedy strikes. Dead Poets Society covers many hard topics such as familial rejection, grief, and suicide. Above all, this film sends an important message of individuality and seizing life’s most adventurous opportunities. As Keating famously says, “Seize the day, boys. Make your lives extraordinary.” 

Dead Poets Society can be streamed on Prime Video and Apple TV.