10 Most Y2K Movies Ever, Ranked Worst To Best

The most iconic movies of the Y2K era focus on either one of the contrasting genres of high school drama or an apocalyptic scenario, with some rom-coms and self-discovery plots also appearing. In the early 2000s, stars including Lindsay Lohan and Hilary Duff were making their most famous movies, in which they dressed in the era’s most popular fashion trends. CGI technology was limited, so action sequences were more reliant on more practical elements to hype up the stars, including leather and sunglasses ensembles, heavy metal and rock music, and strategic staging.

The high school sub-category of Y2K movies typically includes a happy ending, where friends reconcile, teenagers find some common ground with their strict parents, and the girl gets the guy. The protagonists of more serious movies might be forced to sacrifice something along the way to save the world or just a small group of friends. While the most famous movies of this genre did come out within a few years of Y2K, select movies from the mid- to late-2000s still demonstrate significant Y2K themes and motifs.

10 A Cinderella Story (2004)

A modern version of Cinderella with Hilary Duff and Jennifer Coolidge.

In A Cinderella Story, Hilary Duff plays Sam, an orphaned teenage girl approaching graduation with dreams of going to Princeton. She works tirelessly for her stepmother Fiona (Jennifer Coolidge) but has an online friendship with an anonymous persona who turns out to be the school’s football star Austin (Chad Michael Murray). Sam floats onto the prom dance floor dominated by mean girls in short skirts wearing her friend and co-worker Rhonda’s (Regina King) old wedding dress.

A Cinderella Story’s plot doesn’t make sense at some points; the message is ham-fisted and the villains are so bad they are almost comical. Fiona essentially steals Sam’s inheritance while the mean girls stage a skit in front of the entire school, revealing Sam to be the mysterious “Cinderella.” But in the end, Sam sells all Fiona’s stuff to pay for college and inspires Austin to quit football, so it all works out.

9 The Lizzie McGuire Movie (2003)

The movie companion of Duff’s quintessential 2000s TV show.

The early 2000s was the era of popular Disney TV shows That’s So Raven and Lizzie McGuire, which respectively launched Raven-Symoné and Duff to fame. Duff plays the title character Lizzie, a 13-year-old girl whose true thoughts and emotions are expressed through her animated alter ego. The Lizzie McGuire Movie follows Lizzie and her friends on a class trip to Rome after middle school graduation. While Disney Channel’s movies and TV shows are not exactly known for stellar writing, Lizzie McGuire is a beloved character. The format of her animated persona speaking her thoughts is especially fun and unique.

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8 Charlie’s Angels (2000)

Lui, Diaz, and Barrymore strike a pose.

While the movie adaptation of the Charlie’s Angels TV show is average and the entire franchise’s depiction of “empowered women” is problematic, Lucy Lui, Cameron Diaz, and Drew Barrymore are the ultimate trio as Alex, Natalie, and Dylan, respectively. There are a lot of explosions and fights as the Angels race to retrieve stolen voice recognition software, occasionally pausing for a classic Charlie’s Angels pose for dramatic effect. Despite average reviews, the Charlie’s Angels movies seem to be popular among audiences: 2000’s movie was followed by a sequel, while Elizabeth Banks’ Charlie’s Angels reboot holds a 52% Rotten Tomatoes score against a 78% audience score.

7 Chicken Little (2005)

An underrated Disney movie where the sky is falling.

Chicken Little has average at best reviews but is an underrated Disney animated feature with a soft apocalypse plot. The title character “Chicken Little” mistakenly believes the sky is falling and is mocked by his town of nursery rhyme characters – only for a real alien invasion to descend upon them. Chicken Little’s gang of friends notably includes Abby Mallard, a.k.a. the “Ugly Duckling,” along with other hilarious characters. Chicken Little is fun and has a satisfying ending despite the characters peacefully resolving the alien invasion. The movie also features songs including the Spice Girls’ “Wannabe” and Elton John and Kiki Dee’s “Don’t go breaking my heart.”

6 Legally Blonde (2001)

Elle Woods stars in a 2000s classic and starts a fashion trend.

Legally Blonde tells a campy yet popular story about Reese Witherspoon’s Elle Woods, a bubbly aspiring lawyer. Elle follows an ex-boyfriend to Harvard Law School hoping to win him back, only to discover her true passion for using the law to fight for the underdog. Elle arriving in court in hot pink business attire was a defining moment in early 2000s fashion. The main character following a man who doesn’t think she is good enough for him isn’t very inspirational, but she realizes in turn that he isn’t good enough for her. Elle goes on to become a brilliant lawyer and surround herself with supportive friends.

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5 The Fast and the Furious (2001)

The first outing with Dom Toretto and his crew.

The Fast and the Furious kicked off the action-crime franchise just after Y2K, and perhaps no scene in the movie is more characteristic of the era than the original crew pulling up to the Torettos’ café, each in a different sports car. The first movie follows undercover cop Brian O’Connor (Paul Walker), who questions his assignment when he befriends street racer Dom Toretto (Vin Diesel) and his family. The Fast and the Furious is surprisingly down-to-earth when compared to the increasingly flashy Fast & Furious movies of the 2010s. The first movie primarily focuses on Dom and Brian’s tense dynamic and Brian reevaluating his priorities.

4 Freaky Friday (2003)

The comedy classic about a mother and daughter who switch bodies.

Lindsay Lohan was also a defining star of the early 2000s, appearing in Mean Girls and Freaky Friday back to back. In the latter movie, Lohan plays punk-rock teenager Anna, who has a difficult relationship with her mother Tess, played by Jamie Lee Curtis. Everything changes when they wake up to find that they have switched bodies, and they are forced to live each other’s lives for one Friday. Mother and daughter ultimately return to their own bodies and their relationship improves after they have been forced to walk a mile in each other’s shoes. A Cinderella Story’s Chad Michael Murray also appears as Anna’s crush Jake.

3 10 Things I Hate About You (1999)

A modern high school retelling of “Taming of the Shrew.”

10 Things I Hate About You is loosely based on Shakespeare’s The Taming of the Shrew, demonstrating the 2000s trend of modern Shakespearean retellings (She’s the Man came out in 2006). In 10 Things I Hate About You, an overprotective father will only let his younger daughter go to prom with a guy if his older anti-social daughter also has a date. The movie makes the implicit characterization of the corresponding Shakespeare character explicit by depicting Kat as anti-establishment, with a taste for indie rock and feminist prose. 10 Things I Hate About You also features early-career performances by Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt.

2 Mean Girls (2004)

The movie that brought the world “On Wednesdays, we wear pink.”

Tina Fey and Rachel McAdams star alongside Lohan in Mean Girls, one of the quintessential movies of the 2000s. Mean Girls invented many iconic expressions and is rife with the best and worst of the era’s fashion trends. Additionally, its depiction of a toxic high school social environment resonated with many teenagers. Mean Girls is ultimately about these teenagers realizing that bullying each other helps no one. As the characters in the movie begin their senior year, they resolve their differences and become more mature people. Therefore, Mean Girls captures the Y2K high school theme but depicts a healthy alternative to it all.

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1 The Matrix (1999)

The Wachowskis’ landmark sci-fi movie shows the result of a machine uprising.

Coming out just before Y2K, The Matrix embodied all the end-of-world fears in the form of a now iconic sci-fi adventure. The movie’s story of Neo realizing his destiny as the One had a huge impact on pop culture and its special effects techniques were groundbreaking. While the action sequences are still largely reliant on costuming and choreography to make Neo and Trinity look formidable, the CGI that does appear holds up well. The Matrix reflects just one shade of Y2K cinema, which includes everything from high school adventures to college romances to super-powered heroes saving the world.