1999 Movies: Looking Back on One of the Greatest Film Years (2024)

Welcome to our latest recurring feature,The Year in Film! So much of our coverage is devoted to the here-and-now of movies, and that’s all well and good. We’re still going to be bringing you that coverage. But we also love film history, so we thought it would be good to do a weekly series where we look back at a random year and design what made it special. That includes looking at the top-grossing movies, the Oscar winners, and some gems that you should put on your radar.

This week we’re headed to 1999. Let’s kick things off with the top-grossing movies:

Top 10 at the Box Office

1) Star Wars: Episode 1 – The Phantom Menace - $924,317,558

2) The Sixth Sense - $672,806,292

3) Toy Story 2 - $485,015,179

4) The Matrix - $463,517,383

5) Tarzan - $448,191,819

6) The Mummy - $415,933,406

7) Notting Hill - $363,889,678

8) The World Is Not Enough - $361,832,400

9) American Beauty - $456,296,601

10) The Blair Witch Project - $312,016,858

Obviously the beginning of the Star Wars prequels was the biggest box office story of the year, but this is also the year that a Julia Roberts romcom outgrossed a James Bond movie. Indeed, romantic comedies were still flying pretty high in 1999, even as the landscape of film was changing. We were a year away from X-Men, which would forever change the superhero movie genre, and dramas like American Beauty still had a shot at becoming box office juggernauts. Horror was also on top in 1999, as The Sixth Sense and The Blair Witch Project proved to be mainstream hits, while Pixar proved Toy Story wasn’t a fluke with the massively successful Toy Story 2.

Oscar Winners

• Best Picture – American Beauty
• Best Director – Sam Mendes, American Beauty
• Best Actor – Kevin Spacey, American Beauty
• Best Actress – Hilary Swank, Boys Don’t Cry
• Best Supporting Actor – Michael Caine, The Cider House Rules
• Best Supporting Actress – Angelina Jolie, Girl, Interrupted

Yes indeed, American Beauty was an Oscar juggernaut, and in addition to Best Picture, Director, and Actor it also won Best Original Screenplay. And yet, it’s a film few people talk about these days unless they’re mocking its perceived pretention. It’s probably one of the worst-aged recent Best Picture winners, but at the time the film was all anybody could talk about. It’s also crazy to think Spike Jonze and M. Night Shyamalan both landed Best Director nominations in 1999 for Being John Malkovich and The Sixth Sense, respectively.

History

When talking about “great movie years,” 1999 is widely regarded as one of the best years for film ever. While the Oscars may have acknowledged forgotten dramas like The Cider House Rules, this was the year that gave us Being John Malkovich, The Matrix, The Iron Giant, The Sixth Sense, Fight Club, Magnolia, Three Kings and The Talented Mr. Ripley. When you want to talk about how important the Oscars are, 1999 is a great example of how quality will always win out in the end. These films have aged tremendously and gone on to spur repeated viewings and discussions, and they pushed the medium of film to new limits be it David Fincher’s visceral satire, Paul Thomas Anderson’s herculean ambition, or The Wachowskis’ complete reinvention of hard sci-fi.

The year also played host to Ron Howard’s EDtv, which at the time seemed like a shameless cash-in on the reality TV craze but in hindsight is shockingly prescient. And Will Smith’s career cooled after the box office disaster that was Wild Wild West.

Classics

Office Space – Mike Judge spawned a thousand movie quotes with a film about banality.

The Matrix – Pure original cinema. While The Matrix wears its influences on its sleeves, The Wachowskis’ unique approach to this sci-fi actioner forever changed how action movies were made with the introduction of bullet time and extensive wire work.

10 Things I Hate About You – Yes this is a classic with a killer soundtrack. Fight me.

The Mummy – Universal revived its horror classic with an Indiana Jones-tinged twist, and you know what, it still holds up.

Election – Filmmaker Alexander Payne’s second film put both him and Reese Witherspoon on the map big time.

Star Wars: Episode I – The Phantom Menace – Kids love to watch Jedi talkin’ about taxes.

Notting Hill – Four Weddings and a Funeral screenwriter Richard Curtis writes more one-liners to make your heart melt.

American Pie – The revival of the American sex comedy begins here.

Eyes Wide Shut – Stanley Kubrick sadly passed away before completing work on this magnum opus, but even if the finished version was never approved by the filmmaker it left a lasting, perplexing impression. Initial reactions were muted, but it’s now hailed as a masterpiece.

The Blair Witch Project – The birth of the micro-budget thriller, and Hollywood didn’t even know it. Imitations of the budgeting strategy wouldn’t come until ParanormalActivity, but this indie was one of the first films to take advantage of the burgeoning internet in a genius way.

South Park: Bigger, Longer & Uncut – The South Park guys made a movie, fought the MPAA, and got nominated for an Oscar.

The Iron Giant – Brad Bird’s directorial debut was not only a classic in its own right, but a sign of great things to come.

The Sixth Sense – Leave it to M. Night Shyamalan to bring back the “twist ending,” although these expectations would hinder initial reactions to his next few films. Still, the word of mouth around this movie at the time was insane.

Bowfinger – An underrated comedic gem starring Steve Martin as a low-level producer who tries to make a movie starring a huge star (Eddie Murphy) who does not know he’s in a film.

American Beauty – Say what you will about the plastic bag, the performances in this are still pretty terrific.

Three Kings – Filmmaker David O. Russell takes on the Gulf War in hilarious, visually stunning fashion. Tension on set was fraught, leading to a physical fight between Russell and star George Clooney, but the finished product is a delight.

Fight Club – David Fincher’s fourth film was famously a box office bomb and reviews were unkind, but the dark satire gained a devoted following on home video. All’s well that ends well, even if there’s still a large portion of fans who misunderstand the point of Fight Club—it’s not celebrating masculinity, it’s satirizing it.

Bringing Out the Dead – Martin Scorsese reteamed with frequent screenwriter Paul Schrader (Taxi Driver) on this story of a paramedic starring Nicolas Cage. It was a box office and critical bomb, but remains a fascinating entry in Scorsese’s filmography. He would follow it up by finally realizing his passion project Gangs of New York three years later.

The Insider – Filmmaker Michael Mann’s masterful story of a whistleblower who helped shine a light on shady dealings in the tobacco industry. Russell Crowe landed an Oscar nomination, but it’s still sorely underrated.

Dogma – Kevin Smith tackled his biggest budget yet to delightful results with this treatise on religion and faith, starring Alanis Morrissette as God.

Sleepy Hollow – After Superman Lives was scuttled, Tim Burton turned his attention back to horror and made a new classic.

Toy Story 2 – The Pixar sequel was famously originally supposed to go direct to DVD, but when the studio changed its mind John Lassetter took over as director and completely overhauled the story less than a year before release.

The Green Mile – Filmmaker Frank Darabont made a massive hit with 1994’s Stephen King adaptation The Shawshank Redemption, and while this next King adaptation was highly anticipated, it fell somewhat short of expectations.

Galaxy Quest – A comedy classic and one of the best Star Trek movies ever made.

Magnolia – Paul Thomas Anderson took ambition to another level in crafting this nearly three-hour dramatic epic, which even he admits today is too long. Still, the craft, performances, and pacing of Magnolia is a sight to behold.

The Talented Mr. Ripley - The late, great Anthony Minghella’s novel adaptation features a chilling turn by Matt Damon in what still stands as one of the best performances of his career.