The A24 horror-comedy movieY2Kincorporates many elements of 1999 culture.Y2Ktakes place on New Year’s Eve as 1999 comes to an end and 2000 begins. However, in this version of history, the worst fears about the"Year 2000 Problem"come to life. Despite the fictional premise, the movie is a reminder of the memorable popular culture and cinema that defined 1999. The 1990s are frequently looked back on with a great deal of nostalgia that culminated in 1999.

From the1990s' best detective movieslikeSevento thebest fantasy horror movieslikeThe Nightmare Before Christmas, the decade was filled with enduring cinematic achievements. In terms of 1999 culture, the year is partly defined by the memorable movies that were released that year. Other movies areable to capture 1999 culture by encapsulating the humor, widespread interests, common problems, and everyday items that were ubiquitousat the end of the twentieth century.

Y2K 2024 Film Poster

Y2K

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On the last night of 1999, two high school juniors crash a New Years Eve party, only to find themselves fighting for their lives in this dial-up disaster comedy.

Directed by Kyle Mooney,Y2Ksees teenagers Eli (Jaeden Martell), Danny (Julian Dennison), and Laura (Rachel Zegler) fighting to survive as technology tries to destroy humanity.Y2K’s major deathsfeature characters being killed by memorable 1990s toys and technology, with arguably the most memorable being a Tamogotchi driving a drill into one of the characters' brains. Tamogotchis were a popular toy in 1999. Other memorable deaths include being killed by a VHS tape and CDs, which were respectively used for watching movies and listening to music in 1999 and in the years afterward.

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Y2K Ending Explained

Y2K’s ending comes at an darkly absurd and surprisingly bloody cost, and highlights humanity’s best chance against a ruthless enemy like evil A.I.

Beyond Tamogotchis, VHS tapes, and CDs, the horror-comedy movie also showcases the desktop computers of 1999, which were far bulkier than the computers of today. At the beginning of the movie,Eli instant messages Danny and Laura on AOL’s AIM, which was frequently used in 1999 and in the early 2000s, and predated MySpace, Facebook, and many other forms of social media.Y2Keven stars amajor 1990s' iconwith Limp Bizkit’s Fred Durst, who plays himself in one of the movie’s surprisingly prominent roles.

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Austin Powers: The Spy Who Shagged Me

Austin Powers: The Spy Who Shagged Me is the sequel to Jay Roach’s 1997 film, Austin Powers: International Man of Mystery. This time, Dr. Evil devises a plan to time-travel back to the ’60s to steal Austin Powers' mojo. Heather Graham replaces Elizabeth Hurley as Austin Powers' main love interest in this sequel.

Austin Powers: The Spy Who Shagged Mewas released in 1999 and the movie partly takes place during this year as well.The Jerry Springer Show, which was still running and quite popular in 1999, plays an important role in the second installment of theAustin Powers movie series. Dr. Evil (Mike Myers) reunites with his son, Scott Evil (Seth Green), onThe Jerry Spring Showand later in the movie,The Jerry Springer Showis used to reveal to Scott that he is the child of Dr. Evil and Frau Farbissina (Mindy Sterling).

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The harsh realities ofrewatching theAustin Powersmoviesshow that they have not aged well in many respects. However,the now outdated humor resonated strongly in 1999, withAustin Powers: The Spy Who Shagged Mebeing the third highest grossing movie at the domestic box office that year with $206 million (viaBox Office Mojo). OnlyStar Wars: Episode I - The Phantom MenaceandThe Sixth Senseearned more domestically, and the secondAustin Powersmovie financially outperformed the likes ofToy Story 2andThe Matrix.

Fanboys

Fanboys, released in 2009, follows a group of Star Wars enthusiasts who embark on a cross-country road trip to steal a copy of Star Wars: Episode I – The Phantom Menace before its official release. Directed by Kyle Newman, the film stars Dan Fogler, Jay Baruchel, Kristen Bell, and Christopher Marquette. Set in 1998, this comedy captures the fervent excitement of fandom and the enduring bond of friendship.

Fanboysdid not come out until 2009, but it effectivelycaptures the anticipation leading up to the 1999 release ofStar Wars: Episode I - The Phantom Menace.The prequel became the highest grossing movie of the year both domestically and internationally (viaBox Office Mojo). The 2009Fanboysrevolves around the reunion of former high school friends who plan to sneak into Skywalker Ranch so they can see the long-awaited first installment of George Lucas' prequel trilogy.

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Many did camp outside movie theaters for weeks to be among the first to seeThe Phantom Menace.

While real-life fans did not go to this level of extremes, many did camp outside movie theaters for weeks in order to be among the first to seeThe Phantom Menace, which the characters do later in the movie. Decades later, when newStar Warstelevision showsand other new stories are frequently being released, it can be difficult to understand the craze building to the release ofThe Phantom Menace, the franchise’s first movie since 1983.Fanboysgives a taste of what that was like in 1999, albeit in extreme fashion.

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The Matrix

The Matrix, released in 1999, is set in the 22nd century and follows a computer hacker, Neo, portrayed by Keanu Reeves. He joins a group of underground insurgents led by Morpheus to combat the domineering computers that control the earth, in a battle that blurs the lines between reality and illusion.

Few movies can revolutionize the entertainment industry and embody the year they were released as well asThe Matrixdoes. The first movie in the Wachowskis' franchise does this best by introducing the now iconic concept of the Matrix. Many elements of the Matrix concept have aged well, but in 1999, it was particularly perfect in its ability to tap into many of the questions and fears revolving around the rise and evolution of technology and its impact on everyday life.

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The Matrix Resurrections

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The Matrixproved that a blockbuster action movie filled with spectacle could also be a philosophical and thought-provoking exploration of difficult questions and ideas. Christopher Nolan’sInceptionand other movies that came in later years would never have been able to successfully take this approach without the precedent set byThe Matrix.The story of Neo (Keanu Reeves) is a product of its time while also being able to stand the test of timein ways that could not have been foreseen in 1999.

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Big Daddy

Big Daddy is a 1999 comedy film by director Dennis Dugan. Sonny Koufax (Adam Sandler) has gone the first 32 years of his life avoiding any responsibility. But when his girlfriend dumps him out of the blue and shacks up with an older man, he’s confronted by the need to prove he’s got a plan for life to win her back. As a strike of luck, 5-year-old Julian (Dylan and Cole Sprouse) is dropped off on his doorstep, and to impress her, he pretends to be Julian’s father.

Adam Sandler’s popularity existed before and after 1999, but in that year, he was best known forBig Daddy. Sandler plays the lackadaisical Sonny Koufax who has to take care of Julian McGrath, a child character played by a young Dylan and Cole Sprouse. While critics did not loveBig Daddy, a combination of Sandler’s trademark comedy mixed with a more emotional story proved to be a box office hit, and Sonny Koufax is still considered one ofAdam Sandler’s best characters.

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LikeAustin Powers: The Spy Who Shagged Me,Big Daddycan be a reminder of what was considered funny in 1999, althoughBig Daddyhas definitely aged better than the secondAustin Powersmovie. Both the best and worst of Sandler’s comedies in the decades sinceBig Daddywas released often harken back to the humor of the 1990s.Billy Madison,Happy Gilmore, andThe Waterboyare memorable Sandler movies from the 1990s, but Big Daddy was his last big movie of the decade.

The Blair Witch Project

The Blair Witch Project is a 1999 horror film that follows three film students who venture into the Black Hills near Burkittsville, Maryland. As they document their search for the Blair Witch legend, strange and unsettling events unfold. Presented as found footage, the film is directed by Daniel Myrick and Eduardo Sánchez, and it pioneered the found footage genre in mainstream cinema.

The Blair Witch Projectwasthe biggest surprise breakout hit of 1999. Made on a budget of only $60,000,The Blair Witch Projectwent on to make $140.5 domestically and $240.6 million worldwide, making it the tenth highest grossing movie at the domestic box office and the eleventh highest worldwide (viaBox Office Mojo). The movie helped popularize the use of “found footage,” leading toParanormal Activity,Cloverfield, and numerous other movies in the years to come.

The Blair Witch Projectwas a precursor to entertainment largely revolving around people using their devices to document stories that take on a life of their own.

While many of 1999’s highest grossing movies did have large budgets,The Blair Witch Projectis a reminder of a time when an independent movie with a small budget could still become a box office hit. The way that the “found footage” is presented through the cameras of the time is noticeably different from the quality of filmed documentation in the years to follow.The Blair Witch Projectwas a precursor to entertainment largely revolving around people using their devices to document stories that take on a life of their own.

V/H/S/99

V/H/S/99 is the fifth installment in the horror anthology film franchise, which centers around five unrelated stories of terror explored through video tapes in 1999. Six directors come together to tell five tails that examine the fates of those captured on the recordings, each with ghostly, gruesome, and unsettling results.

The titleV/H/S/99automatically brings to mind VHS tapes, the main way of watching movies at home in 1999.V/H/S/99is the fifth movie in theV/H/Sfranchise that isinspired by the “found footage” horror popularized by 1999’sThe Blair Witch Project. As the title suggests,V/H/S/99takes place in 1999 as an anthology of four short horror movies, with the premise involving each horror story being a disturbing segment found on a VHS tape.

The first story, “Shredding,” involves a web show hosted by members of a punk rock band. 1999 was a time when web series were becoming more commonplace, although they were a far cry from the series of videos that would dominate the Internet in the years to come. The cameras used throughout the movie reflect the technology of 1999. Out of all theV/H/S/movies, this is the best one for looking back at 1999 culture.

Office Space

Office Space is a satirical comedy movie by Mike Judge, the creator of Beavis and Butthead and King of the Hill. Peter Gibbons, the film’s protagonist, is overworked, underpaid, and over it all as his work continues to wreak havoc on his personal life and mental health. One day during a hypnosis session, Peter’s therapist dies mid hypnosis leaving Peter in a perpetual state of calm, where he is no longer bothered by the trivial elements of the world. With a changed outlook and a devil-may-care attitude, Peter’s newfound love of life starkly contrasts with the rest of the world and the hustle approach evident in American work culture.

Mike Judge’sOffice Spacetells a story of employees at a software company who are fed up with their jobs. The 1999 comedy’s legacy is now heavily intertwined with memes, but it is representative of the time that it was made. The once exciting frontier of computer software had now been turned into another form of tedious office work. Frustrations with this are captured throughOffice Space, but anyone frustrated with their job can relate as well.

Office Space’s humor is representative of 1999, but has endured because of the commonplace and daily frustrations that it builds upon. Unlike other movies made in and associated with 1999,Office Spacewas not a box office hit. Nevertheless, its home video sales and transformed into a cult classic movie thatencapsulates office work life and humor in 1999, which are helpfully preserved by the abundance ofOffice Spacememes.

American Pie

American Pie is a 1999 teen comedy that follows four high school friends as they enter a pact to lose their virginity before college. The film explores their comedic and often awkward attempts to fulfill this goal, set against the backdrop of typical high school experiences and senior prom.

To experience the raunchy humor of 1999 movies, one need look no further than the firstAmerican Pie, which was released that year. The infamous scene of Jim (Jason Biggs) filming Nadia (Shannon Elizabeth) without her consent has aged horribly and is a reflection of some humor that should never have been appealing in the first place. That being said, itfeels like 1999 to have this live stream filming conducted through AOL chat rooms, which is a sign of the times.

There are now 9American Piemovies.

The clothes worn by theAmerican Piecharactersreflect the clothing style of the 1990s and the soundtrack is reflective of the latter portion of the decade as well. There have been many sequels and spinoffs since the first movie, but none are as memorable as the original. This is partly because of how much the late 1990s is linked to the movie’s style, and this was never done as effectively in the years when the various sequels and spinoffs were released.

10 Things I Hate About You

Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is a modern retelling of the classic play, set against the backdrop of a 90s Seattle high school. When social outcast Patrick Verona is paid to try and win over antisocial Kat Stratford in order so her younger sister will be allowed to date, he and Kat find an unexpected connection forming between them. Julia Stiles and Heath Ledger star as Kat and Patrick, with a further cast that includes Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, and Larry Miller.

10 Things I Hate About Youwas made as a modernized retelling of the William Shakespeare comedic playThe Taming of the Shrew. The comedy movie starring Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt is no longer a modern story, but it does an effective job of capturing high school culture and the styles of 1999.The10 Things I Hate About Yousoundtrack features covers performed byLetters to Cleo, a band popular in the 1990s.

American Pieis the ultimate raunchy teen comedy of 1999, but10 Things I Hate About Youis the ultimate teenager-focused romantic comedy of that year. The outfits and general fashion are still looked back on fondly as a sign of what was popular in 1999.10 Things I Hate About Youis now both a Shakespeare retelling and a beloved 1999 movie. It may have little in common with 2024’sY2K, but both are emblematic of 1999 culture.