16 Best Movies & Shows Released in 1999

Staff & contributors

Find the best movies and show to watch from the year 1999. These handpicked recommendations are highly-rated by viewers and critics.

From the legendary Hayao Miyazaki, and courtesy of Studio Ghibli, which also brought you Spirited Away, comes this epic whirlwind of a story. Set during a fantastical late Muromachi period, the medieval era of Japan, in a time when many humans were still living among nature, while others set out to conquer and tame it, the movie follows a young man named Ashitaka, who he seeks cure for the curse of a boar god, giving him superhuman powers but eventually killing him. He rides west on a fantastic beast, where he eventually sees a young woman named San, also known as Princess Mononoke. What unfolds from here, is an epic tale of mythical war on many fronts, between the nature gods and humans. While this may sound like a dichotomy, it never is that morally simplistic. The story is action-packed and fast-paced, drawing freely from Japanese mythology as well as modern hot-topic political issues. Add to this the fantastic visuals: Hayao Miyazaki uses a mixture of hand drawings and 3D rendering that are nothing short of spectacular. In short, Princess Mononoke is movie history. If you haven't seen it yet, do it now.

Genre: Adventure, Animation, Fantasy

Actor: Akihiro Miwa, Akira Nagoya, Akira Sakamoto, Alex Fernandez, Billy Bob Thornton, Billy Crudup, Claire Danes, Corey Burton, Daikichi Sugawara, Debi Derryberry, Gillian Anderson, Hisaya Morishige, Ikuko Yamamoto, Jada Pinkett Smith, John DeMita, John DiMaggio, Kaoru Kobayashi, Keith David, Makoto Satō, Masahiko Nishimura, Minnie Driver, Mitsuko Mori, Mitsuru Satô, Shiro Saito, Sumi Shimamoto, Takako Katou, Tara Strong, Tetsu Watanabe, Tsunehiko Kamijo, Yayoi Kazuki, Yôji Matsuda, Yoshimasa Kondô, Youji Matsuda, Yûko Tanaka, Yuriko Ishida

Director: Hayao Miyazaki

Rating: PG-13

The bare bones of The Limey’s story — vengeful Cockney ex-con Wilson (Terence Stamp) flies to LA to investigate the suspicious death of his daughter Jenny — are gripping enough, but what Steven Soderbergh does with them elevates this neo-noir thriller into something utterly singular and stacked with layers upon layers of meaning. An icon of London’s Swinging ‘60s scene, Stamp is pitted against laidback symbol of ‘60s American counterculture Peter Fonda (as Jenny’s sleazy older boyfriend), giving their face-off grander cultural stakes. The extra-textual significance of the casting is deepened by Soderbergh’s ingenious references to the actors’ heyday: in flashbacks to Wilson’s happier past, for example, we’re shown the actual Stamp in his younger years (courtesy of scenes borrowed from 1967’s Poor Cow).

The Limey is also a brilliant showcase for editor Sarah Flack’s technical inventiveness: though the narrative is largely linear, the film cuts to and from scenes and sounds at unexpected points, giving the film an almost David Lynch-like sense of eerie fragmentation. Conjuring up a nightmare LA atmosphere isn’t all the editing does, either, as the film’s puzzle pieces are expertly reassembled to reveal an emotional gut-punch of an ending. In short, this high point in Soderbergh’s filmography is a must-see for any fan of cinema.

Genre: Crime, Drama, Mystery

Actor: Allan Graf, Amelia Heinle, Barry Newman, Bill Duke, Brandon Keener, Carl Ciarfalio, Carol White, Clement Blake, George Clooney, Joe Dallesandro, John Cothran, John Robotham, Johnny Sanchez, Lesley Ann Warren, Luis Guzman, Matthew Kimbrough, Melissa George, Michaela Gallo, Nancy Lenehan, Nicky Katt, Peter Fonda, Rainbow Borden, Randy Lowell, Steve Heinze, Terence Stamp, Wayne Pére, William Lucking

Director: Steven Soderbergh

Rating: R

Starring Matthew Broderick and a young Reese Witherspoon as, respectively, Jim McAllister, a high school teacher and Tracy Flick, a notorious 'that girl' in his class. When Tracy decides to run for class president, we see the floodgates open as all sorts of bizarre and insane behavior pours out of the two. Quickly, it becomes clear that Tracy will do nearly anything to win, and as circumstances spiral out of control, madness descends - along with hilarity!

Genre: Comedy, Drama, Romance

Actor: B.J. Tobin, Chris Klein, Colleen Camp, Delaney Driscoll, Frankie Ingrassia, Holmes Osborne, Jason Paige, Jeanine Jackson, Jessica Campbell, John Ponzio, Kaitlin Ferrell, Mark Harelik, Matt Malloy, Matthew Broderick, Molly Hagan, Nicholas D'Agosto, Phil Reeves, Reese Witherspoon

Director: Alexander Payne

Rating: R

Set in war-torn Berlin during World War II, this film explores the forbidden romance between a married mother of four and a Jewish woman working undercover for the resistance based on the real lives of Lilly Wust and Felice Schragenheim, as detailed in Erica Fischer's book of the same name. As expected, all of the frightening challenges of Jewish people, women, and queer folks are presented bluntly. But there are enough touching and humane moments of empathy that contrast the harsh realities of war. The performances by Maria Schrader and Juliane Köhler are simply remarkable, bringing depth and authenticity to their characters' intense connection and creating a poignant viewing experience. 

Genre: Drama, History, Romance

Actor: Dani Levy, Désirée Nick, Detlev Buck, Dorkas Kiefer, Elisabeth Degen, Heike Makatsch, Johanna Wokalek, Juliane Köhler, Maria Schrader, Rosel Zech, Ulrich Matthes

Director: Max Färberböck

David O. Russel (Silver Linings Playbook, American Hustle) is one of those directors who the more you dig into his past, the more you are rewarded. I Heart Huckabees is a great example of this, as is The Fighter (both are must-watch if you haven't seen them). But it is Three Kings that truly presented him as someone who can give great substance to big-budget movies. It stars George Clooney, Mark Wahlberg, Ice Cube, and even director Spike Jonze (Her, Adaptation), in other words, a festival of talent at its peak. And it follows three soldiers who want use the end of the Gulf War as an opportunity to get rich. Their journey through a devastated and uncertain Iraq is a thrilling one, as Three Kings is action-packed. But the purpose of this movie lies somewhere between political satire around American interventionism and social criticism of the main characters. However, none of that stands in the way of this movie being an entertaining and exhilarating movie.

Genre: Action, Comedy, War

Actor: Ali Afshar, Alia Shawkat, Brian Bosworth, Cliff Curtis, David O. Russell, Doug Jones, Dylan Brown, George Clooney, Holt McCallany, Ice Cube, Jamie Kennedy, Jim Gaffigan, Jon Sklaroff, Judy Greer, Liz Stauber, Mark Wahlberg, Mykelti Williamson, Nora Dunn, Rick Shuster, SaÁ¯d Taghmaoui, Saïd Taghmaoui, Sayed Badreya, Spike Jonze

Director: David O. Russell

Rating: R

Often considered Claire Denis’ best film, Beau Travail is an epic exploration of both masculinity and colonialism. Inspired by Melville’s Billy Budd, she transplants the story to Djibouti where the French Foreign Legion run seemingly aimless drills in an arid desert landscape while largely alienated from the local community. 

Denis inverts the male gaze and imbues charged eroticism to the bodies in motion as the men train and wrestle. Accompanied by the music of Britten’s Billy Budd opera, these movements transform into a breathtaking modern dance. Underneath her jaw-dropping direction is a cutting allegory on repression, desire, and violence, working on both the individual and geopolitical level. This incredible tale is capped off by one of the best end credit sequences of all time. 

Genre: Drama

Actor: Dan Herzberg, Denis Lavant, Gianfranco Poddighe, Grégoire Colin, Michel Subor, Mickael Ravovski, Nicolas Duvauchelle

Director: Claire Denis

Rating: Unrated

Audition is not for the faint of heart. It's shockingly violent and deeply unsettling, filled with sights and sounds that will haunt you for days on end. But there is grace to its terror; it's profound and artistic in ways that elevate it from generic horror fare.

On a deeper level, Audition is about the destructive power of abuse, trauma, and loneliness, about how a society that neglects to recognize this eventually suffers from it. The revenge plot isn't merely individual, as well, but a representation of the female subconscious: tired of objectification, eager for redress. And everything about the way the film is made, from the shaky camera and titled frames to the dramatic shadows and eerie lighting, reflects that imbalance. 

Audition may be chilling and gruesome, but it's also smart and important, a psychosexual thriller that captures female anger well before it became the rage. 

Genre: Drama, Horror

Actor: Eihi Shiina, Fumiyo Kohinata, Jun Kunimura, Kanji Tsuda, Ken Mitsuishi, Miyuki Matsuda, Ren Osugi, Renji Ishibashi, Ryo Ishibashi, Shigeru Saiki, Tatsuo Endō, Tetsu Sawaki, Toshie Negishi, Yuriko Hirooka

Director: Takashi Miike

Rating: R

Directed by Tsai Ming-liang, this unconventional story follows the lives of two neighbors who share a crumbling apartment in the midst of a strange, inexplicable epidemic. Blending a quiet drama with exciting musical numbers, the characters' lives intertwine in unexpected ways, blurring the line between reality and fantasy. With its masterful use of long takes and minimal dialogue, there is a haunting atmosphere that lingers in every shot. In hindsight, this film perfectly captures our recent pandemic-stricken world; the effects of cabin fever condensed in absurd trippy sequences. As with many Tsai Ming-liang films, it is a must-watch for fans of simpler, yet mesmerizing, art-house cinema.

Genre: Drama, Romance, Science Fiction

Actor: Chen Shiang-Chyi, Lee Kang-sheng, Lu Yi-Ching, Miao Tien, Yang Kuei-Mei, Yee Chin-Yen

Director: Tsai Ming-liang

What Lynne Ramsay's Ratcatcher intentionally refuses to give you by way of plot or resolution, it more than makes up for in sharp visuals, a beautifully sparse score, and an unscratchable feeling of restlessness. It's a downer for sure, watching 12-year-old James hounded by guilt as he navigates the mundane bleakness of his everyday life. But in every detail and in every interaction he has in this rundown scheme in Glasgow is a window into the simple joys James wishes he could be enjoying. The more trouble the boy walks into, the more the guitar string tightens, and the more you wish something could finally break the cycle. There's still beauty even in these conditions, Ratcatcher tells us—but it isn't right that anyone should have to live like this.

Genre: Drama

Actor: Jackie Quinn, Leanne Mullen, Lisa Taylor, Rory McCann, Tommy Flanagan

Director: Lynne Ramsay

One of Studio Ghibli’s overlooked gems, My Neighbors the Yamadas is a charming anthology film about a modern-day Japanese family. The film sets itself apart from other Ghibli films through its unique doodle-like watercolor animation and its short piano themes. While the vignettes may just depict regular family conflicts, the scenes still feel compelling due to the Yamadas’ imagination of the metaphors that they use. Exaggerating the metaphors keeps the audience breathless in certain strategic moments - most notably in the wedding day speech of the mother of the bride. While not as fantastical as Ghibli’s other offerings, the completely digital My Neighbors the Yamadas finds humor in and celebrates the mundane.

Genre: Animation, Drama, Family

Actor: Akiko Yano, Chôchô Miyako, Hayato Isohata, Masako Araki, Naomi Uno, Tamao Nakamura, Toru Masuoka, Yukiji Asaoka

Director: Isao Takahata

Rating: PG

If you're a fan of musical theater of any kind, Topsy-Turvy pays tribute to that notoriously tricky art form with a stunning attention to detail and a dedication to telling its story without any unnecessary drama whatsoever. It's hard not to get swept up in the humor, entertainment, and simple joy found in the writing process and in rehearsals of entire scenes. Come for the Oscar-winning costumes and makeup, stay for the wonderfully old-timey musical numbers, the brilliantly grounded performance from Jim Broadbent, and the sense of satisfaction of just watching everything finally come together to thunderous applause.

Genre: Comedy, Drama, History, Music

Actor: Akemi Otani, Alison Steadman, Allan Corduner, Andy Serkis, Angela Curran, Anna Francolini, Ashley Artus, Ashley Jensen, Bríd Brennan, Cathy Sara, Charles Simon, Debbie Chazen, Dexter Fletcher, Dorothy Atkinson, Eiji Kusuhara, Eleanor David, Eve Pearce, Francis Lee, Gemma Page, Geoffrey Hutchings, Heather Craney, Jim Broadbent, John Warnaby, Jonathan Aris, Julia Rayner, Julian Bleach, Kacey Ainsworth, Katrin Cartlidge, Kenneth Hadley, Kevin McKidd, Lavinia Bertram, Lesley Manville, Louise Gold, Mark Benton, Martin Savage, Mary Roscoe, Matt Bardock, Matthew Mills, Mia Soteriou, Michael Simkins, Monica Dolan, Naoko Mori, Nicholas Boulton, Nicholas Woodeson, Nick Bartlett, Paul Barnhill, Richard Coyle, Roger Heathcott, Ron Cook, Rosie Cavaliero, Sam Kelly, Shirley Henderson, Sophie Duval, Steve Speirs, Sukie Smith, Teresa Gallagher, Timothy Spall, Togo Igawa, Vincent Franklin, Wendy Nottingham

Director: Mike Leigh

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Jack Betts, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Kinna McInroe, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, Richard Riehle, Ron Livingston, Stephen Root, Todd Duffey

Director: Mike Judge

Rating: R

Tied together by a song that seems to drive people to end their own lives, Gloomy Sunday's tale of polyamorous love torn apart by the advent of the Second World War is one that doesn't operate according to your usual narrative structure. Its stranger elements might not always work with the very real horrors of the Nazis' invasion of Hungary, but the film still expresses this horror in a unique way. Even long before the war begins, this song that joins our three lovers together seems to touch on a sense of doom everybody is feeling—warning signs of Hitler's rise to power that ordinary people seem to have been powerless to stop in time. It's certainly unique for a non-action-driven war film, bathed in tragedy and bitter irony.

Genre: Drama, History, Romance, War

Actor: András Bálint, Ben Becker, Denis Moschitto, Dorka Gryllus, Erika Marozsán, Ferenc Némethy, Joachim Krol, Karl Fischer, László I. Kish, Markus Hering, Márta Bakó, Rolf Becker, Sebastian Koch, Stefan Weinert, Stefano Dionisi, Veit Stübner, Wanja Mues

Director: Rolf Schübel

Galaxy Quest may be a parody of the sci-fi franchise, but it’s also a huge fan of it. It forgoes cynical takes for smart odes to the genre, all while retaining an endearing sense of humor about it. It’s silly and self-aware, and it has a lot of fun letting us know that they’re in on the joke. You can watch for the interesting premise, but you'll stay for the laughs and the promise of a genuine thrill ride. Everyone is a blast to watch, but Sigourney Weaver and Sam Rockwell deserve special praise for being outright hilarious, elevating Galaxy Quest from B-movie to camp classic status. 

Genre: Adventure, Comedy, Drama, Science Fiction

Actor: Alan Rickman, Corbin Bleu, Daryl Mitchell, Dian Bachar, Enrico Colantoni, Heidi Swedberg, Isaac C. Singleton Jr., J.P. Manoux, Jed Rees, Jennifer Manley, Jeremy Howard, Joel McKinnon Miller, Justin Long, Kaitlin Cullum, Kevin McDonald, Marcio Rosario, Matt Winston, Missi Pyle, Morgan Rusler, Patrick Breen, Rainn Wilson, Robin Sachs, Sam Lloyd, Sam Rockwell, Sigourney Weaver, Tim Allen, Todd Giebenhain, Tony Shalhoub

Director: Dean Parisot

Rating: PG