movies

'1999 was the best year in the history of movies. Let me prove why.'

Tonight I'm gonna party like it's 1999 and by party, I mean watch all the movies that premiered 25 years ago in this unrivalled year in cinema.

There was something in the water in 1999. I say this without any hint of hyperbole: there will never (ever, ever, ever) be a year for movies that comes close to the slate of films released this year.

Why did 1999 have so many of the best movies?

At the time, Entertainment Weekly published the headline ‘1999: The Year That Changed Movies', writing that this year sparked a new era as "the old, boring rules about cinema started to crumble".

Film journalist Brian Raftery dedicated an entire book to the blessed year, aptly titled Best. Movie. Year. Ever: How 1999 Blew Up the Big Screen, as he wrote 1999 was "the most unruly, influential and unrepentantly pleasurable film year of all time."

These movies nailed every single genre while offering the sorts of films that broke barriers, challenged norms and started new trends in storytelling.

Don't believe me? Read 'em and weep (like quite literally, we will never recapture this magic again *audibly sobs*).

I've rounded up the 22 most iconic movies of 1999 but let it be known: this is just scraping the surface, there are so many gems.

1. 10 Things I Hate About You.

10 Things I Hate About You is a beyond iconic teen romantic comedy starring Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt. Based on Shakespeare's The Taming of the Shrew, it follows a high school romance plot involving sisters Kat and Bianca Stratford.

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The film launched several careers and remains a cultural touchstone, praised for its feminist messages, hilarious dialogue and of course, Ledger's swoon-worthy musical number.

Image: Bueno Vista.

2. Notting Hill.

Notting Hill is arguably the greatest romantic comedy of all time, bringing together Hugh Grant and Julia Roberts for one perfect film. It tells the story of a travel bookshop owner who falls in love with a famous American actress.

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The film's charming portrayal of London's most photogenic borough and its witty script made it a cultural phenomenon, influencing rom-coms for years to come and not to mention giving a big tourism boost to the Notting Hill area.

3. Cruel Intentions.

This movie was about as sick and twisted as a teen film could get. Cruel Intentions starred Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair, and followed two wealthy step-siblings who make a wager involving the seduction of a virtuous girl.

The film gained cult status for its provocative themes, gritty soundtrack, iconic scenes like the kiss between Gellar and Blair, influencing pop culture and teen cinema for generations.

4. Jawbreaker.

Another absolute transformative film, Jawbreaker was a dark comedy starring Rose McGowan, Rebecca Gayheart, Judy Greer and Julie Benz. The plot revolves around a popular high school clique accidentally killing their friend during a prank gone wrong involving a (you guessed it) jawbreaker.

It wasn't a huge box office success but the film eventually gained a cult following for its satirical take on teen culture, strong fashion choices and influential high school aesthetic.

Image: Sony Pictures.

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5. Girl, Interrupted.

Girl, Interrupted is a psychological drama based on Susanna Kaysen's memoir. It follows Susanna (Winona Ryder) during her stay at a mental institution, where she befriends a group of troubled women, including the manipulative Lisa (Angelina Jolie) and the disturbed Daisy (Brittany Murphy).

The powerful (albeit very controversial) film sparked discussions about mental health and earned Jolie an Oscar.

6. Fight Club.

It's hard to describe just how huge this movie was but I'd hazard a guess that it still tops a lot of people's favourite movie lists. Directed by David Fincher, Fight Club follows an insomniac office worker who forms an underground fight club with a mysterious man, Tyler Durden.

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Starring Edward Norton and Brad Pitt, the film explores themes of masculinity, mental health and consumerism, and comes with one hell of a twist ending.

7. The Virgin Suicides.

Another absolute cult fave, The Virgin Suicides is a film directed by Sofia Coppola about five teenage sisters in 1970s suburban Detroit who tragically die by suicide. It stars Kirsten Dunst and Joshua Hartnett just as their careers were taking off and the film's dreamy aesthetic and exploration of adolescent angst made it a cult classic.

Image: Paramount Classics.

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8. The Mummy.

The Mummy still stands as one of the greatest action flicks of all time, as it follows adventurer Rick O'Connell (Brendan Fraser) and librarian Evelyn Carnahan (Rachel Weisz) as they accidentally awaken an ancient Egyptian mummy. Oopsie. The consequences are scary but also, hilarious. The film revitalised the monster movie genre, spawning several sequels and cementing Fraser's stardom.

9. American Pie.

It's difficult to summarise just how huge this movie was in its day. Despite some often problematic messages about teenage girls, the film launched the careers of Jason Biggs, Alyson Hannigan and Seann William Scott.

Following four high school boys who make a pact to lose their virginity before graduation, American Pie marked a return to the teen sex comedy genre, coined the term 'MILF' and introduced the infamous apple pie scene.

10. The Matrix.

Another super influential offering to the action genre, The Matrix follows hacker Neo (Keanu Reeves) as he discovers the world is a simulation controlled by machines. Sounds confusing but it works, okay!

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Alongside Morpheus (Laurence Fishburne) and Trinity (Carrie-Anne Moss), Neo fights for humanity's freedom. The film's groundbreaking special effects, philosophical themes, and iconic scenes were considered to have revolutionised cinema and popular culture.

Image: Warner Bros.

11. American Beauty.

This movie swept the 2000 Academy Awards, taking home five Oscars. American Beauty, directed by Sam Mendes, explores suburban disillusionment through the story of Lester Burnham's midlife crisis when he becomes enamored by a teenage girl.

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Starring Kevin Spacey, Annette Bening, Thora Birch and Mena Suvari, this irreverent drama casts a harsh lens on American values, materialism and societal expectations.

12. Eyes Wide Shut.

Eyes Wide Shut was Stanley Kubrick's final film, bringing together then-married actors Tom Cruise and Nicole Kidman as a married couple exploring sexual temptation and jealousy. The plot follows Dr. Bill Harford's nocturnal journey through New York City, culminating in a mysterious masked orgy. Despite mixed reviews upon release, the movie has since become a beloved erotic thriller.

13. She's All That.

When it comes to iconic teen films, She's All That will top anyone's list. Starring Freddie Prinze Jr. and Rachael Leigh Cook as our opposites-attract couple, the plot revolves around a popular jock who bets he can transform a nerdy artist into the prom queen. Paul Walker and Matthew Lillard round out the cast. She's All That influenced teen movies for years to come and popularised the high school makeover trope.

Image: Miramax Films.

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14. Election.

This satirical comedy starring Reese Witherspoon and Matthew Broderick was largely overlooked at the time but has since been hailed as a cult classic. The plot revolves around a high school student council election, providing sharp wit and prescient commentary on American politics.

15. Toy Story 2.

If you ask any well-adjusted adult about the movie that made them tear up in the '90s, Pixar's masterpiece Toy Story 2 would immediately come to mind. The first movie was light-hearted enough but the second delved deeper into how kids outgrow their toys and what happens when they do. Spoiler: devastation.

Tom Hanks and Tim Allen returned to voice unlikely adversaries Woody and Buzz Lightyear. The story begins when Woody is stolen by an unhinged toy collector, as Buzz and their toy friends embark on a rescue mission.

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16. The Sixth Sense.

1999 has range! Alongside teen comedies and kid's films, there's arguably the greatest psychological thriller of the 20th century.

Directed by the king of creep, M. Night Shyamalan, The Sixth Sense starred Bruce Willis as a child psychologist helping a young boy (Haley Joel Osment) who claims to see the ghosts of deceased people. The movie's famous line, "I see dead people," became heavily parodied, as did its twist ending to end all twist endings.

Image: Buena Vista.

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17. The World is Not Enough.

Oh yeah, 1999 also featured an iconic James Bond movie. No biggie! The World Is Not Enough was the 19th James Bond film, starring Pierce Brosnan as 007. The plot revolves around protecting an oil heiress from a terrorist, featuring Sophie Marceau and Denise Richards as some iconic Bond Girls.

18. Varsity Blues.

In a year that boasted so many amazing movies, it's worth noting just how HUGE Varsity Blues was, despite it losing a lot of its hype over the years. The sports drama film starred James Van Der Beek during his Dawson's Creek era, with the teen heartthrob playing a high school quarterback in a small Texas town obsessed with football. The film also features memorable performances from Jon Voight as the tyrannical coach and the late Paul Walker as the star player.

19. Austin Powers: The Spy Who Shagged Me.

Again… the range of 1999!! The impact of this movie on culture in 1999 was basically unrivalled. You couldn't get through a conversation with your friend without someone quoting one of this film's countless catchphrases.

Austin Powers: The Spy Who Shagged Me starred Mike Myers playing both the titular spy and his nemesis Dr. Evil but hosts a whole bunch of unhinged performances from Heather Graham, Seth Green and Rob Lowe. Sure, a lot of the problematic jokes would rightly not fly in the 2020s but it still remains a huge blockbuster of the '90s.

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Image: New Line Cinema.

20. Drop Dead Gorgeous.

When it comes to dark comedies, you don't get much darker than this. Drop Dead Gorgeous is a mockumentary that follows a small-town beauty pageant in Minnesota with biting social commentary about the extent women go to in order to be considered perfect. It stars Kirsten Dunst, Kirstie Alley, a scene-stealing Denise Richards, and helped launch the careers of Amy Adams and Brittany Murphy.

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21. The Blair Witch Project.

Ready to get spooked? This movie reigned in a huge cultural movement. The low-budget The Blair Witch Project follows three student filmmakers who disappear while investigating the local legend of an evil witch residing in the forest.

By using unknown actors, found-footage techniques and embracing a viral marketing campaign, many viewers believed at the time that the film was actually genuine footage featuring real people. The success of the horror movie would spark a huge rush of found-footage horror movies.

22. The Talented Mr. Ripley.

To round out the 1999 movies, this book-to-screen adaption set in 1950s Italy starred Matt Damon as Tom Ripley, a con artist who assumes the identity of a wealthy playboy played by Jude Law.

The Talented Mr. Ripley is rounded out by stellar performances from Gwyneth Paltrow, Cate Blanchett, and the late Philip Seymour Hoffman.

25 years since it's debut, the movie is still as great as ever.

Fyi, there are countless other iconic movies that could have made this list (Boys Don't Cry! The Iron Giant! Dick! Double Jeopardy!) with at least 50 truly incredible movies released in 1999.

A truly magical year in film. Never forget.

Feature image: Universal Pictures/Sony Pictures/Buena Vista.

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