10 Best Movies That Will Send You Back to the Y2K Era, According … – Collider

Travel back to the turn of the millennium with these movies.
The Y2K Era brought about iconic moments and trends in US culture like tracksuits, denim, glamorous pop stars, flip phones, and more. The era also had quite a bit of movies that were produced that portrayed the hottest trends and were often quite humorous in nature. Sadly, the public has shifted out of that brightly-colored and shiny era, but there are a few ways to reminisce upon memories from the 2000s.
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With some of the best Y2K-Era movies available to stream on major streaming platforms, there are a couple of movies from friends on Reddit that could easily transport viewers back to the era of Britney Spears and Justin Timberlake.
10 Things I Hate About You is one of the most famous 2000s movies and one of the best rom-coms to date. The movie follows a smart, pretty, and abrasive teenage girl named Kat (Julia Stiles) who has some trouble catching the attention of available bachelors. Her younger sister isn’t allowed to date until Kat has a boyfriend, so she decides to pull some strings so Kat can fall in love.
When she meets Patrick (Heath Ledger), everything comes together perfectly—Kat just has to let him in! 10 Things I Hate About You is about as Y2K as movies can get, and (fun fact) the film is an adaptation of Shakespeare’s The Taming of the Shrew.
Bring It On is the first in a series of cheerleading films released in the 2000s. The plot focuses on a high school cheerleading squad’s preparation for a national competition. This comedy film follows the new captain of the cheerleading team, Torrance (Kirsten Dunst), as she discovers that the previous captain stole the team’s cheers from another school.
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Now, they must make it to nationals and succeed while handling the complex situation. Bring It On was also a Broadway musical.
The Oscar-winning movie American Beauty was listed multiple times as one of the best films of the Y2K era on Reddit forums. American Beauty follows a telesales operative who becomes more self-aware and decides he wants more for his life. He tries to take more interest in his children and family, and his life takes a couple of turns for the worst as the plot progresses.
Cheating, scandals, spying, and more take place in this film. While the film does star Kevin Spacey, who is now embroiled in sexual assault allegations, American Beauty as a movie (without him) is a strong example of a Y2K drama.
She’s All That is a very popular romantic comedy that is ever so reminiscent of the Y2K era. In this high school film, a kid named Zach (Freddie Prinze Jr.) is jealous of his classmates. When his popular cheerleader girlfriend dumps him for a reality-television star, he agrees to a challenge: gain the trust of an outcast named Laney (Rachael Leigh Cook) and help her become the school’s next prom queen.
This movie is iconic and is the blueprint for many other high school movies that have followed. She’s All That is a perfect film to watch for a dose of comedy and nostalgia.
Bridget Jones’s Diary is a British film about a 32-year-old woman named Bridget (Renée Zellweger) who decides that she wants to finally take control of her life. So, she keeps a diary that contains everything she wishes to happen in her life.
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The movie is a reinterpretation of Jane Austen’s Pride and Prejudice. Two men waltz into her life and fight for her love. The film is quite enjoyable and is an absolute classic among romantic comedies.
One of the most iconic teen comedy movies of all time is Mean Girls. Written by Tina Fey, Mean Girls follows a young girl named Cady (played by Lindsay Lohan, pronounced like “Katie”) who moves from homeschooling in Africa to an American high school. As she adjusts to American high school culture, she learns who the popular “plastics” are and how she can become one of them.
On her uphill climb to popularity, she gains friends, loses friends, and—with others—becomes more than friends. This hilarious film should be a must-watch for anyone interested in the Y2K era.
Scary Movie is a 2000s horror parody movie. The film follows a group of teenagers who accidentally hit someone with their car, killing him. They hide his body in a lake and plan never to speak of the situation again.
A year later, a masked killer begins to kill them one by one. While the film seems to be scary, what Scary Movie (and what the subsequent sequels) do so well is bring in other horror movie themes and parody or create spoofs of them. The film is so funny and is the perfect Y2K watch for the Halloween season.
As one of the most famous children’s films of the 2000s, Spy Kids is an action comedy film. The film follows two kids, Carmen (Alexa Vega) and Juni (Daryl Sabara), who find out that both of their parents (and themselves) are spies.
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They try to rescue their parents from an evil mastermind (played by the incomparable Alan Cumming) by becoming spies themselves. For any 2000s kids, Spy Kids will bring back so many fond memories of a simpler time.
Charlie’s Angels is an iconic all-women action series about a trio of elite private investigators that must track down a kidnapped future billionaire and new technological software from evil hands.
With high-tech gadgets, vehicles, martial arts fighting techniques, and disguises, these three investigators bring it all. Charlie’s Angels is a wonderfully intense film that everyone should try watching.
The Matrix is one of the most famous and well-known movies in the history of cinema. The film brought about the rise to fame of Keanu Reeves, who plays Neo, a man who discovers that the world he lives in is not at all what it seems and is merely an illusion that covers up an entirely different world.
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However, once one person discovers the secret, an army of top secret agents quickly moves on the case to prevent the public from knowing the truth. This dystopian-action film is a perfect watch for the Y2K era nostalgia.
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Riley is a new Lists Writer for Collider! Hailing from the tri-state area of the United States, Riley has extensive knowledge on all things, TV, Comedy, Film, and even Theatre. He has a secret love for some specialty topics on the “geekier” side (looking at you, Marvel) and strives to create open spaces for Queer identities.


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