29 Best Movies & Shows Released in 1999

released › 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.

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, 1999

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, Kiho Iinuma, Kimihiro Reizei, Makoto Satō, Masahiko Nishimura, Minnie Driver, Mitsuko Mori, Mitsuru Satô, Shiro Saito, Shirou Saitou, Sumi Shimamoto, Takako Katou, Tara Strong, Tetsu Watanabe, Tsunehiko Kamijo, Tsuzuki Kayako, Yayoi Kazuki, Yôji Matsuda, Yoshimasa Kondô, Youji Matsuda, Yûko Tanaka, Yuriko Ishida

Director: Hayao Miyazaki

Rating: PG-13

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, 1999

Director Jim Jarmusch audaciously combined the DNA of French noir classics with that of samurai and mafia movies to produce this utterly original film. As advised by the ancient Japanese manual it often quotes, though, Jarmusch’s movie also “makes the best” out of its own generation by adding hip-hop into its wry genre blend. The results are more than the sum of their parts, especially because the film is so eccentric: no matter how au fait with its inspirations you are, you still won’t see “Forest Whitaker plays a lonely hitman who wields and whooshes his silencer pistol like a samurai sword, lovingly tends pigeons, and can’t even speak the same language as his best friend” coming.

Ghost Dog’s strangeness is never jarring, though, thanks to Whitaker’s cool, collected performance, an atmospheric score by Wu-Tang Clan's RZA, and the cinematography’s tendency to use smooth double exposures for scene transitions. It almost feels like we’re in another world: Jarmusch zooms in on the Bushido code obsessions of Whitaker’s single-minded character and the mafiosos’ dying laws, blurring out everything else so the movie becomes a meditation on the impulse to moralize one’s misdoings by subscribing to rigid definitions of “honor.” Not an exercise in surface style, then, but a bone-deep reflective masterpiece.

Genre: Crime, Drama

Actor: Alfred Nittoli, Angel Caban, Camille Winbush, Chuck Jeffreys, Clebert Ford, Cliff Gorman, Damon Whitaker, Forest Whitaker, Frank Adonis, Frank Minucci, Gano Grills, Gary Farmer, Gene Ruffini, Harry Shearer, Henry Silva, Isaach De Bankolé, Jamie Hector, Jerry Todisco, John Tormey, Jonathan Teague Cook, José Rabelo, Joseph Rigano, Paul Diomede, Renee Bluestone, Richard Portnow, Roberto Lopez, RZA, Scott Bryce, Sharon Angela, Tony Rigo, Tracy Howe, Tricia Vessey, Victor Argo, Vince Viverito, Vinny Vella

Director: Jim Jarmusch

Rating: R

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Shot from the movie

, 1999

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, Thriller

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

Director: Steven Soderbergh

Rating: R

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, 1999

Kimberly Peirce's first–out of only three—film was a smashing success, mostly due to her dedication to the subject matter. Peirce spent years researching the life and tragic death of Brandon Teena after reading an article about him in The Village Voice. She felt a particular kind of kinship as a queer person herself, and wanted to construct a story out of real facts that would put the spotlight on love and the desire for connection, and not that much on the violence which dominated the public discourse. In Falls City, Nebraska, the director conducted interviews with Lana Tisdale (Brandon's girlfriend) and her mother, while attending the ongoing trial. She took years to cast the lead and from hundreds of cis women, lesbians, and trans people, she chose the unknown actress Hilary Swank, who went on to win the Best Actress Academy Award (and the irony of that is not lost on us). The film features fantastic performances aplenty and very raw storytelling, visualized by neorealist style and low lighting. Direct references were the films of Martin Scorcese and John Cassavetes, but Boys Don't Cry has its own blend of beauty and cruelty to take pride in.

Genre: Crime, Drama

Actor: Alicia Goranson, Alison Folland, Brendan Sexton III, Caitlin Wehrle, Cheyenne Rushing, Chloe Sevigny, Craig Erickson, Gabriel Horn, Gail Cronauer, Gavin Perry, Guilford Adams, Hilary Swank, Jackson D. Kane, Jeannetta Arnette, Jerry Haynes, Josh Ridgway, Libby Villari, Lisa Renee Wilson, Lou Perryman, Matt McGrath, Paige Carl Griggs, Peter Sarsgaard, Rob Campbell, Robert Prentiss, Shana McClendon, Stephanie Sechrist

Director: Kimberly Peirce

Rating: R

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, 1999

Martin Scorsese — plus screenwriter Paul Schrader, editor Thelma Schoonmaker, and cinematographer Robert Richardson — reimagine nocturnal New York City as an eternally flaming circle of hell in this darkly funny fever dream. Frank Pierce (Nicolas Cage) is an insomniac paramedic who’s haunted by the ghosts of all the lives he couldn’t save and is on a nightmarish run of losing every patient he tries to help. There’s no respite for him anywhere; he’s so burnt out he begs to be fired, but the city is so desperate they won’t let him leave their tired ranks of medics, who are mostly jaded, sometimes sadistic, and yet still addicted to the euphoric high of saving a life.

As Frank is pushed ever closer to breaking point, the film takes on the hallucinatory qualities of his perspective, the cinematography growing feverish and the editing powered by a wild, manic energy. What stops the movie from feeling like a spiral into actual hell is the strange light that keeps Frank returning to work — the perpetual need for redemption and grace that prevents him from becoming cold to his job but makes his sanity fragile. In typical Scorsese-Schrader style, this is a raw, visceral, and very human search for grace in an unsparing urban hellscape.

Genre: Drama, Horror, Thriller

Actor: Afemo Omilami, Aida Turturro, Aleks Shaklin, Andy Davoli, Antone Pagán, Arthur J. Nascarella, Bernie Friedman, Betty Miller, Brian Smyj, Bronson Dudley, Catrina Ganey, Charis Michelsen, Cliff Curtis, Craig muMs Grant, Cullen O. Johnson, David Zayas, Ed Jupp Jr., Floyd Resnick, Frank Ciornei, Fuschia!, Graciela Lecube, Jack O'Connell, James Hanlon, Jesse Malin, John Goodman, John Heffernan, Jon Abrahams, Joseph P. Reidy, Judy Reyes, Julyana Soelistyo, Larry Fessenden, Leonid Citer, Lia Yang, Marc Anthony, Mark Giordano, Martin Scorsese, Mary Beth Hurt, Mary Diveny, Marylouise Burke, Matthew Maher, Melissa Marsala, Michael Carbonaro, Michael Kenneth Williams, Michael Mulheren, Mtume Gant, Nestor Serrano, Nicolas Cage, Omar Scroggins, Patricia Arquette, Phyllis Somerville, Queen Latifah, Raymond Cassar, Richard Spore, Sonja Sohn, Sylva Kelegian, Terry Serpico, Theo Kogan, Tom Cappadona, Tom Riis Farrell, Tom Sizemore, Ving Rhames

Director: Martin Scorsese

Rating: R

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Shot from the movie

, 1999

Rosetta begins fiercely, with a shaky handheld camera chasing the eponymous teenager (Émilie Dequenne) as she storms across a factory floor and bursts into a room to confront the person she believes has just lost her her job. The film seldom relents from this tone of desperate fury, as we watch Rosetta — whose mother is a barely functioning alcoholic — fight to find the job that she needs to keep the two alive.

As tough as their situation is, though, Rosetta’s fierce sense of dignity refuses to allow her to accept any charity. A stranger to kindness and vulnerability, her abject desperation leads her to mistake these qualities for opportunities to exploit, leading her to make a gutting decision. But for all her apparent unlikeability, the movie (an early film from empathy endurance testers the Dardenne brothers) slots in slivers of startling vulnerability amongst the grimness so that we never lose sight of Rosetta’s ultimate blamelessness. Its profound emotional effect is corroborated by two things: that it won the Palme d’Or at Cannes, and that it helped usher in a law protecting the rights of teenage employees in its setting of Belgium.

Genre: Drama

Actor: Anne Yernaux, Bernard Marbaix, Émilie Dequenne, Fabrizio Rongione, Florian Delain, Frédéric Bodson, Mireille Bailly, Olivier Gourmet, Sophia Leboutte, Valentin Traversi

Director: Jean-Pierre Dardenne, Luc Dardenne

Rating: R

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Shot from the movie

, 1999

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, Mystery, Romance

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

Director: Alexander Payne

Rating: R

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Shot from the movie

, 1999

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: Barbara Focke, Dani Levy, Désirée Nick, Detlev Buck, Dorkas Kiefer, Elisabeth Degen, Heike Makatsch, Jochen Stern, Johanna Wokalek, Juliane Köhler, Klaus Manchen, Kyra Mladeck, Marc Bischoff, Maria Schrader, Peter Weck, Rosel Zech, Ulrich Matthes

Director: Max Färberböck

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Shot from the movie

, 1999

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: Al Whiting, Ali Afshar, Alia Shawkat, Anthony Batarse, Brian Bosworth, Christopher B. Duncan, Cliff Curtis, David O. Russell, Doug Jones, Dylan Brown, George Clooney, Holt McCallany, Ice Cube, Jamie Kennedy, Jay Giannone, Jim Gaffigan, Joey Naber, Jon Sklaroff, Joseph Romanov, Judy Greer, Liz Stauber, Mark Wahlberg, Mykelti Williamson, Nora Dunn, Peter Macdissi, Qaid Al-Nomani, Rick Shuster, SaÁ¯d Taghmaoui, Saïd Taghmaoui, Salah Salea, Sayed Badreya, Shawn Pilot, Spike Jonze, Tank Jones, Tony Shawkat

Director: David O. Russell

Rating: R

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Shot from the movie

, 2000

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: Adiatou Massudi, Bernardo Montet, Dan Herzberg, Denis Lavant, Gianfranco Poddighe, Giuseppe Molino, Grégoire Colin, Marc Veh, Michel Subor, Mickael Ravovski, Nicolas Duvauchelle, Richard Courcet

Director: Claire Denis

Rating: Unrated

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Shot from the movie

, 1999

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, Kimiko Tachibana, Miyuki Matsuda, Ren Osugi, Renji Ishibashi, Ryo Ishibashi, Shigeru Saiki, Tatsuo Endō, Tetsu Sawaki, Toshie Negishi, Yuriko Hirooka

Director: Takashi Miike

Rating: R

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Shot from the movie

, 1999

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

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Shot from the movie

, 1999

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, James Ramsay, John Comerford, Leanne Mullen, Lisa Taylor, Mandy Matthews, Mick Maharg, Molly Innes, Robert Farrell, Rory McCann, Tommy Flanagan

Director: Lynne Ramsay

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Shot from the movie

, 1999

October Sky doesn’t tread new ground—in fact, you’ll be forgiven for rolling your eyes at a couple of cliches, including the classic “Those are your dreams, dad, not mine!” moments—but it’s so unassuming and well-made that it’s hard not to get drawn in by its many charms. There’s Gyllenhaal’s breakthrough performance for one, and the small town coming together to help each other out for another. Perhaps because the film is based on Homer Hickman’s true story, it also feels more specific and lived in than most period pieces. And it smartly avoids villainizing young Hickam’s adversaries so that they feel more real and nuanced, as opposed to the other far-fetched parts of the film. Sure, the overuse of sweeping music can feel cloying at times, but stellar performances across the board and confident direction overall make it a heartwarming, inspiring winner.

Genre: Drama, Family

Actor: Andy Stahl, Blaque Fowler, Brady Coleman, Chad Lindberg, Charles Lawlor, Chris Cooper, Chris Ellis, Chris Owen, Courtney Cole-Fendley, Dave Hager, David Dwyer, Don Henderson Baker, Doug Swander, Elya Baskin, Frank Hoyt Taylor, Jake Gyllenhaal, Joe Digaetano, John Bennes, Kaili Hollister, Larry Black, Laura Dern, Mark Jeffrey Miller, Mark W. Johnson, Natalie Canerday, Neva Howell, Randy Stripling, Rick Forrester, Scott Thomas, Terrence Gibney, Terry Loughlin, Tom Turbiville, Tommy Smeltzer, William Lee Scott

Director: Joe Johnston

Rating: PG

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