10 Nostalgic Sleepover Movies To Watch This Summer

10 Nostalgic Sleepover Movies To Watch This Summer

High School Musical 2 is due to celebrate its fifteenth anniversary this summer, bringing a wave of nostalgia for fans who watched it when it first came out in the late 2000s. This movie has likely to have been watched during many summer sleepovers, along with not just others in the franchise but other chick flick movies of the ’00s.

Sleepover movies often contained stories that tweens and teens alike could enjoy among friends, typically on long summer nights. Featuring the trials of the teenage girl, sleepover movies are rich with laughs and life lessons. Whether reliving the movie-filled nights of their teen years or are simply interested in some early Y2K fashion and mall culture, these movies well-enjoyed by sleepover parties are a perfect match for anyone searching for some nostalgia.

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Clueless (1995)

Alicia Silverstone in Clueless

The cult classic Clueless is a staple to both movie-goers and childhoods alike. Whether because of its iconic lines or a young Paul Rudd, this popular, feel-good chick flick holds a place in countless memories as an integral story of teenage culture, making it a perfect sleepover hit.

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Clueless’s journey of a privileged, mall-obsessed teen finding emotional understanding is timelessly hilarious. Aside from its plot, the preppy outfits of characters Cher, Dionne, and eventually Tai were so trendsetting that they are still found in fashion today.

Angus, Thongs And Perfect Snogging (2008)

Angus, Thongs And Perfect Snogging was a film sympathetic to many 14-year-olds trying to navigate puberty along with the other trials of tween life. A helpful guide to those back in the day, this movie is, in the present, a nostalgic reflection of tribulations long overcome.

This English film is filled with flirting, crushes, and of course, snogging (kissing), which are stereotypically all vital experiences to both teenage characters and viewers alike. Others remember the film for romantic awakenings brought on by heartthrob Robbie (Aaron Taylor-Johnson) who sang the film’s memorable original song, “Ultraviolet.”

Aquamarine (2006)

Aquamarine

Aquamarine was a nautical favorite for the sleepover crowds, offering a touching story that proved true love wins, whether romantic or between best friends. As one of the best mermaid movies, this film is perfect for anyone who had a childhood obsession with the finned creatures as well as a good relationship with their friends.

While the plot might seem silly to today’s standards, Aquamarine was beloved to tweens for its titular character, Aquamarine (Sara Paxton), who sported enviable blue-dyed hair and mood-changing nails. The wholesome unfolding of Aquamarine and lifeguard Raymond’s relationship is nostalgic of a time when love was simple and halter dresses were cool.

Mean Girls (2004)

Mean Girls Group

It’s hard to meet anyone who hasn’t seen Mean Girls these days, even if they weren’t introduced to the movie via a sleepover party. Created with the involvement of comedic actor Tina Fey, this early 2000s flick is hilarious to all ages, even though its plot is centered around teenage girls.

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Despite its wide audience, this film tackles many girl-oriented issues, including the too-real stereotype of the “Mean Girl.” The main antagonist Regina George (Rachel McAdams) has established herself, in true character, as the unforgettable face of this trope, setting the foundation for dozens of “mean girl” characters for years to come.

10 Things I Hate About You (1999)

Kat (Julia Stiles) and Patrick (Heath Ledger) in a paddle boat in 10 Things I Hate About You.

Romance is a key theme in many sleepover movies, and one of the genre’s most-watched love stories is 10 Things I Hate About You, based on Shakespeare’s The Taming Of The Shrew. The film transform’s the poet’s classic characters into struggling high schoolers who, relatably, grapple with young love in a captivating, convoluted plot.

10 Things I Hate About You takes a break from the Cher-like popular protagonist, and offers Kat (Julia Stiles), a defiant, indie-loving feminist who gave a voice to the teenage viewers who hated conformity, as well as representing alternative fashion. Of course, many young viewers remember the film for its handsome bad-boy Patrick (Heath Ledger), who captured many young hearts with his accent and iconic singing scene.

Legally Blonde (2001)

Legally Blonde 3 stars Reese Witherspoon as Elle Woods.

One of   Reese Witherspoon’s establishing films, Legally Blonde taught many young girls that being both feminine and brainy is a good thing. It’s no doubt that it found favor in groups of teens, as the empowering Elle Woods proved that one did not have to forgo pink, “girly” outfits in order to graduate from Harvard Law.

Overall, Legally Blonde offers a fun, witty story that is just as enjoyable today as it was in 2000. Unsurprisingly, Reese Witherspoon delivers a top-notch performance that excels beyond the screen surrounded by teens.

The Princess Diaries (2001)

The Princess Diaries was a favorite sleepover movie for many reasons, but mostly because it imbued the fantasy that anyone could secretly be a princess. Any young viewer could see themselves as the quirky Mia (Anne Hathaway), who enviably got sucked into a life of royalty.

Donning a popular princess aesthetic, The Princess Diaries was a staple to any group of movie-going girls. Watching today, its leading actors Hathaway and Julie Andrews give funny yet heartwarming performances that still remain treasured.

A Cinderella Story (2004)

Sam (Hilary Duff) in A Cinderella Story

A Cinderella Story was another movie that made teens wish they could be its protagonist, as Sam (Hillary Duff) not only got to be the belle of the prom but had a love interest in Austin (Chad Micheal Murray), a popular first celebrity crush.

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Duff was already popular as the character Lizzy McGuire from the television show of the same name, so it’s no doubt so many loved A Cinderella Story. This movie offers many details nostalgic of the time of Y2K, not just including layered outfits, but a flip phone as a replacement for Cinderella’s lost slipper.

Freaky Friday (2003)

Jamie Lee Curtis and Lindsay Lohan in Freaky Friday

Preceded by versions of the same name made in 1976 and 1995, the 2003 version of Freaky Friday revamped the tale with all things early 2000, ranging from Anna’s (Lindsay Lohan) punk fashion to her band’s iconic song “Take Me Away.”

Though a third movie take of the novel by Mary Rodgers, Freaky Friday remains a nostalgic favorite for not only its Y2K style but its unforgettable plot. Lohan and Jaime Lee Curtis, who plays Anna’s mother, offer a rough but ultimately understanding mother-daughter relationship that will remind many viewers of their own teenage years.

Sleepover (2004)

Steve and Julie in Sleepover (2004)

Sleepover is a natural choice for the genre of the sleepover movie, and not just because of its name. Not only is this movie nostalgic for the party itself, but for a time when groups of friends were called to band together. However, Sleepover’s main cast of girls deals with a lot more than everyday teen trials.

This movie features many notable actors, some popular from other teen movies (Alexa PennaVega from Spy Kids and Sara Paxton from Aquamarine), and others modern favorites shown in their younger years (Brie Larson and Evan Peters). The film even includes Steve Carrell, who personifies the hilarious, goofy themes of the movie as Sherman, a wimpy cop.

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About The Author

Sophia Indelicato
(5 Articles Published)

Sophia is a recent graduate with a degree in Creative Writing, along with minors in Film and Jazz Studies. She’s been analyzing films with her brother since she was young and has seemed to take that hobby a little seriously. Sophia’s goal is to be a screenwriter or scriptwriter, and if that doesn’t work out she plans to be a street performer. When she isn’t hyperfixated on a new show or movie, she’s either writing for her Dungeons and Dragons campaign or reading The Witcher. She also loves making short films. Sophia’s favorite show is either Normal People or Game of Thrones, and her favorite movie is About Time.

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