The A24 horror-comedy movie Y2K incorporates many elements of 1999 culture. Y2K takes 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 the 1990s’ best detective movies like Seven to the best fantasy horror movies like The 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 are able to capture 1999 culture by encapsulating the humor, widespread interests, common problems, and everyday items that were ubiquitous at the end of the twentieth century.
10 Y2K
The A24 Movie Says Farewell To 1999
Y2K
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.
- Release Date
- March 9, 2024
- Writers
- Evan Winter
- Cast
- Rachel Zegler , Alicia Silverstone , Julian Dennison , Jaeden Martell , Eduardo Franco , Mason Gooding , Miles Robbins , Tim Heidecker
- Runtime
- 93 Minutes
Directed by Kyle Mooney, Y2K sees teenagers Eli (Jaeden Martell), Danny (Julian Dennison), and Laura (Rachel Zegler) fighting to survive as technology tries to destroy humanity. Y2K‘s major deaths feature 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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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. Y2K even stars a major 1990s’ icon with Limp Bizkit’s Fred Durst, who plays himself in one of the movie’s surprisingly prominent roles.
9 Austin Powers: The Spy Who Shagged Me
The Title Of The Second Austins Powers Movie Speaks For Itself
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.
- Director
- Jay Roach
- Release Date
- June 11, 1999
- Runtime
- 95 Minutes
Austin Powers: The Spy Who Shagged Me was 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 the Austin Powers movie series. Dr. Evil (Mike Myers) reunites with his son, Scott Evil (Seth Green), on The Jerry Spring Show and later in the movie, The Jerry Springer Show is used to reveal to Scott that he is the child of Dr. Evil and Frau Farbissina (Mindy Sterling).
The harsh realities of rewatching the Austin Powers movies show that they have not aged well in many respects. However, the now outdated humor resonated strongly in 1999, with Austin Powers: The Spy Who Shagged Me being the third highest grossing movie at the domestic box office that year with $206 million (via Box Office Mojo). Only Star Wars: Episode I – The Phantom Menace and The Sixth Sense earned more domestically, and the second Austin Powers movie financially outperformed the likes of Toy Story 2 and The Matrix.
8 Fanboys
The 2009 Movie Captures 1999’s Hype Related To The Phantom Menace
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.
- Director
- Kyle Newman
- Release Date
- February 6, 2009
- Writers
- Ernest Cline , Adam F. Goldberg , Dan Pulick
- Runtime
- 90 Minutes
Fanboys did not come out until 2009, but it effectively captures the anticipation leading up to the 1999 release of Star Wars: Episode I – The Phantom Menace. The prequel became the highest grossing movie of the year both domestically and internationally (via Box Office Mojo). The 2009 Fanboys revolves 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.
Many did camp outside movie theaters for weeks in order to be among the first to see
The 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 see The Phantom Menace, which the characters do later in the movie. Decades later, when new Star Wars television shows and other new stories are frequently being released, it can be difficult to understand the craze building to the release of The Phantom Menace, the franchise’s first movie since 1983. Fanboys gives a taste of what that was like in 1999, albeit in extreme fashion.
7 The Matrix
Neo Taking The Red Pill Changed Everything
9/10
The Matrix
The Matrix, directed by the Wachowskis, stars Keanu Reeves as Neo, a hacker who discovers that reality is a simulated construct controlled by intelligent machines. Laurence Fishburne and Carrie-Anne Moss co-star as Morpheus and Trinity, who help Neo navigate and ultimately challenge the artificial world. The film blends action, philosophy, and groundbreaking visual effects, establishing itself as a pivotal entry in the science fiction genre.
- Director
- Lana Wachowski , Lilly Wachowski
- Release Date
- March 31, 1999
- Writers
- Lilly Wachowski , Lana Wachowski
- Runtime
- 136 minutes
Few movies can revolutionize the entertainment industry and embody the year they were released as well as The Matrix does. 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.
|
Matrix Movie |
Release Year |
|---|---|
|
The Matrix |
1999 |
|
The Matrix Reloaded |
2003 |
|
The Matrix Revolutions |
2003 |
|
The Matrix Resurrections |
2021 |
The Matrix proved that a blockbuster action movie filled with spectacle could also be a philosophical and thought-provoking exploration of difficult questions and ideas. Christopher Nolan’s Inception and other movies that came in later years would never have been able to successfully take this approach without the precedent set by The Matrix. The story of Neo (Keanu Reeves) is a product of its time while also being able to stand the test of time in ways that could not have been foreseen in 1999.
6 Big Daddy
Big Daddy Is The Culmination Of Adam Sandler’s Movies In The 1990s
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.
- Director
- Dennis Dugan
- Release Date
- June 25, 1999
- Runtime
- 93 Minutes
Adam Sandler’s popularity existed before and after 1999, but in that year, he was best known for Big 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 love Big 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 of Adam Sandler’s best characters.
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Like Austin Powers: The Spy Who Shagged Me, Big Daddy can be a reminder of what was considered funny in 1999, although Big Daddy has definitely aged better than the second Austin Powers movie. Both the best and worst of Sandler’s comedies in the decades since Big Daddy was released often harken back to the humor of the 1990s. Billy Madison, Happy Gilmore, and The Waterboy are memorable Sandler movies from the 1990s, but Big Daddy was his last big movie of the decade.
5 The Blair Witch Project
“Found Footage” Leads To An Unexpected And Influential Hit
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.
- Director
- Eduardo Sánchez , Daniel Myrick
- Release Date
- July 30, 1999
- Writers
- Daniel Myrick , Eduardo Sánchez
- Cast
- Joshua Leonard , Michael C. Williams , Heather Donahue
- Runtime
- 81 minutes
- Sequel(s)
- Book of Shadows: Blair Witch 2
The Blair Witch Project was the biggest surprise breakout hit of 1999. Made on a budget of only $60,000, The Blair Witch Project went 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 (via Box Office Mojo). The movie helped popularize the use of “found footage,” leading to Paranormal Activity, Cloverfield, and numerous other movies in the years to come.
The Blair Witch Project
was 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 Project is 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 Project was a precursor to entertainment largely revolving around people using their devices to document stories that take on a life of their own.
4 V/H/S/99
The Fifth V/H/S/ Movie Feels The Most Like 1999
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.
- Director
- Johannes Roberts , Vanessa Winter , Joseph Winter , Maggie Levin , Tyler MacIntyre , Flying Lotus
- Release Date
- October 20, 2022
- Writers
- Johannes Roberts , Maggie Levin , Zoe Cooper , Flying Lotus , Chris Lee Hill , Tyler MacIntyre , Vanessa Winter , Joseph Winter
- Cast
- Verona Blue , Dashiell Derrickson , Ally Ioannides , Isabelle Hahn , Steven Ogg , Amelia Ann , Luke Mullen , Emily Sweet , Joseph Winter , Archelaus Crisanto
- Runtime
- 109 Minutes
The title V/H/S/99 automatically brings to mind VHS tapes, the main way of watching movies at home in 1999. V/H/S/99 is the fifth movie in the V/H/S franchise that is inspired by the “found footage” horror popularized by 1999’s The Blair Witch Project. As the title suggests, V/H/S/99 takes 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 the V/H/S/ movies, this is the best one for looking back at 1999 culture.
3 Office Space
The Cult Classic Comedy Deals With Commonplace Frustrations
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.
- Director
- Mike Judge
- Release Date
- February 19, 1999
- Writers
- Mike Judge
- Runtime
- 89 minutes
- Budget
- $10 million
Mike Judge’s Office Space tells 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 through Office 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 Space was not a box office hit. Nevertheless, its home video sales and transformed into a cult classic movie that encapsulates office work life and humor in 1999, which are helpfully preserved by the abundance of Office Space memes.
2 American Pie
None Of The Sequels Or Spinoffs Have A Legacy As Strong As The 1999 Movie
American Pie
American Pie is a raucous teen comedy and the film that launched a revival of the genre. It follows a group of high school friends determined to lose their virginity before graduation and delves into the misadventures of the four boys as they navigate the complexities of relationships, peer pressure, and parental mishaps. You’ll never look at warm apple pie the same again.
- Director
- Paul Weitz , Chris Weitz
- Release Date
- July 9, 1999
- Writers
- Adam Herz
- Runtime
- 95 minutes
To experience the raunchy humor of 1999 movies, one need look no further than the first American 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, it feels like 1999 to have this live stream filming conducted through AOL chat rooms, which is a sign of the times.
There are now 9
American Pie
movies.
The clothes worn by the American Pie characters reflect 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.
1 10 Things I Hate About You
The Fashion And Soundtrack Are Pure 1999
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.
- Director
- Gil Junger
- Release Date
- March 31, 1999
- Writers
- Karen McCullah , Kirsten Smith
- Cast
- Julia Stiles , Heath Ledger , Joseph Gordon-Levitt , Larisa Oleynik , Larry Miller , Andrew Keegan , David Krumholtz , Susan May Pratt
- Runtime
- 97 minutes
10 Things I Hate About You was made as a modernized retelling of the William Shakespeare comedic play The 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. The 10 Things I Hate About You soundtrack features covers performed by Letters to Cleo, a band popular in the 1990s.
American Pie is the ultimate raunchy teen comedy of 1999, but 10 Things I Hate About You is 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 You is now both a Shakespeare retelling and a beloved 1999 movie. It may have little in common with 2024’s Y2K, but both are emblematic of 1999 culture.
Source: Box Office Mojo, Box Office Mojo, Box Office Mojo
