29 Best Movies & Shows Released in 1999 (Page 2)

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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16. My Neighbors the Yamadas, 1999

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, Kosanji Yanagiya, Masako Araki, Naomi Uno, Tamao Nakamura, Toru Masuoka, Yukiji Asaoka

Director: Isao Takahata

Rating: PG

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17. Buena Vista Social Club, 1999

	
When Castro took over Cuba in the 1950s, Havana’s nightlife shifted as clubs and casinos were closed down, leading to certain traditional step-based genres like son, bolero, and danzón to decline. A few decades later, prominent American musician Ry Cooder travelled to Cuba with his friend documentarian Wim Wenders, to pay homage to traditional Cuban music in an album and its respective documentary. Wenders weaves in illuminating interviews and shots of Cuba today in between the band’s Amsterdam and Carnegie Hall performances, with a certain intuition that makes each song feel like a triumph. While the documentary does focus more on Cooder, Buena Vista Social Club is a delight to watch, even with its 90s digital grain.Genre: Documentary, Music
Actor: Compay Segundo, Eliades Ochoa, Ibrahim Ferrer, Joachim Cooder, Omara Portuondo, Ry Cooder
Director: Wim Wenders
Rating: G

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18. Beyond the Mat, 1999

Tale as old as time: longform wrestling content catered to a general audience kicks things off with disclaimers and explanations of what pro wrestling really is. But director and producer Barry Blaustein also does a fantastic job as narrator, guiding us with friendly fanboy insights through Terry Funk’s sincere inability to retire, the beginning of Jake Roberts’ self-destruction, Mick Foley’s perceived invincibility, and the cacophony of backstage stories in the late ‘90s that the film strings together. As if all that wasn’t enough, so many oddball and iconic skits (i.e. “I’m not booked, Terry”) push this from great to quintessential.

Genre: Documentary

Actor: Accie Julius Connor, Aurelian Smith Jr., Barry W. Blaustein, Chyna, Darren Drozdov, Dave Meltzer, Dwayne Johnson, Jesse Ventura, Joanie Laurer, Mark Calaway, Michael Cariglio, Michael Manna, Mick Foley, Noelle Foley, Paul Heyman, Scott Levy, Steve Austin, Terry Funk, Tony Jones, Vince McMahon

Director: Barry W. Blaustein

Rating: R

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19. Trick, 1999

	
When forming a connection with someone, sometimes it doesn’t go the way you plan to– it’s a familiar romcom thread, something from the classics, but it’s a story that works. Trick is a witty comedy of errors with a similar thread, but through the various obstacles shy gay man Gabriel has in trying to get a one night stand, the romcom neatly introduces him, and us, to Greenwich Village’s gay community of the 1990s: the casual piano bars, the vibrant nightclubs, and the fun drag shows. It’s charming, it’s sweet, it’s humorous, and it has a lighthearted relatable struggle, one that focuses on the joys and pleasures of falling in love as a gay man.Genre: Comedy, Romance
Actor: Brad Beyer, Christian Campbell, Debbie Troche, Eric Bernat, Helen Hanft, Jamie Gustis, Joey Dedio, John Paul Pitoc, Kate Flannery, Kevin Chamberlin, Lacey Kohl, Lorri Bagley, Miss Coco Peru, Missi Pyle, Nat DeWolf, Ralph Cole Jr., Scottie Epstein, Steve Hayes, Tori Spelling, Will Keenan
Director: Jim Fall
Rating: R

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20. Topsy-Turvy, 1999

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

Director: Mike Leigh

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21. The Road Home, 1999

	
With more and more young people moving to the city for jobs, there’s a certain beauty in the countryside that is being missed out. The Road Home is a simple and straightforward love story, one that is mostly composed of Zhang Ziyi as a country girl stealing glances at the handsome city boy who’s come to teach in the village, but there’s a certain magic in the way director Zhang Yimou depicts the rural traditions of the village, the charming and distinct rhythms of life that continues to this day. While the film glosses over the reasons for Luo’s temporary departure, which some reviewers speculate is due to China’s then Anti-Rightist campaign, The Road Home beautifully depicts the way love can bloom despite these troubles, and how this love can shift the lives of an entire town.Genre: Drama, Romance
Actor: Li Bin, Song Yuncheng, Sun Honglei, Yulian Zhao, Zhang Ziyi, Zheng Hao
Director: Zhang Yimou

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22. Office Space, 1999

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, Barbara George-Reiss, Cassie Townsend, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Heath Young, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Josh Bond, Justin Possenti, K. Todd Lytle, Kinna McInroe, Kyle Scott Jackson, Linda Wakeman, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, R.C. Keene, Richard Riehle, Ron Livingston, Rupert Reyes, Samantha Inoue Harte, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

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23. Gloomy Sunday, 1999

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, Anna Ráckevei, Áron Sipos, Ben Becker, Denis Moschitto, Dorka Gryllus, Erika Marozsán, Ernst Kahl, Ferenc Bács, Ferenc Némethy, Ilse Zielstorff, István Kanizsay, István Mikó, Joachim Krol, Jörg Gillner, Karl Fischer, László I. Kish, Markus Hering, Márta Bakó, Michael Gampe, Rolf Becker, Sebastian Koch, Stefan Weinert, Stefano Dionisi, Tibor Kenderesi, Ulrike Grote, Veit Stübner, Wanja Mues, Zsuzsa Mányai

Director: Rolf Schübel

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24. Go, 1999

	
Starting with Columbia Picture’s intro syncing into a rave, director Doug Liman’s sophomore feature Go instantly establishes its ecstatic energy– both in the hyper happy and drug-fuelled way– that made it a cult classic. All in one night, the dark crime comedy culminates in a wild Christmas Eve in three separate storylines: one with dissatisfied checkout girl Ronna, who needs fast cash, another with her drug dealer co-worker Simon going to Vegas, and the last with soap opera actors Adam and Zack, who want to get high while staying out of trouble. The cast is excellent, with witty quips and the twenty-something ennui of that generation, and each decision their characters make to feel good all turns Christmas Eve into a truly awful, yet terribly entertaining ride. While some of the humor is definitely dated, Go captures the insane chaotic energy just right before the new millennium.Genre: Comedy, Crime, Thriller
Actor: AlgeRita Wynn, Breckin Meyer, Courtland Mead, D. Danny Warhol, Dana Schick, Desmond Askew, J. Karen Thomas, J.E. Freeman, James Duval, Jane Krakowski, Jay Mohr, Jay Paulson, Jimmy Shubert, Jodi Bianca Wise, Josh Paddock, Katharine Towne, Katie Holmes, Manu Intiraymi, Melissa McCarthy, Natasha Melnick, Nathan Bexton, Nikki Fritz, Rita Bland, Robert Peters, Sarah Polley, Scott Wolf, Sean Everett, Suzanne Krull, Tane McClure, Taye Diggs, Timothy Olyphant, Tony Denman, William Fichtner, Willie Amakye
Director: Doug Liman
Rating: R

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25. Felicia's Journey, 1999

	
Usually a film like this wouldn’t care to take the perspective of the perpetrator, and would instead dramatize a heavy, unsettling feeling around a victim being caught within their operation. But Felicia’s Journey doesn’t take that route– instead, at the same time, we meet both serial killer and potential victim through a snapshot of their lives, with writer-director Atom Egoyan adeptly intercutting Felicia’s Journey with Hilditch’s video-recorded childhood and Felicia’s much more natural flashbacks. It’s an interesting visual take on the 1994 novel, that doesn’t take the usual thriller motifs and that would rather linger on studying the characters. Felicia’s Journey might be Egoyan’s first non-R rated film, but it still delivers his signature uneasiness and eeriness he is known for.Genre: Drama
Actor: Arsinée Khanjian, Bob Hoskins, Bríd Brennan, Elaine Cassidy, Gerard McSorley, Julie Cox, Kriss Dosanjh, Nizwar Karanj, Peter McDonald, Sandra Voe, Sheila Reid
Director: Atom Egoyan
Rating: PG-13

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26. The Winslow Boy, 1999

	
When a student is accused of stealing something as small as a five shilling postal order, it just seems so miniscule that expelling the child, and the child’s family suing the college, can seem all rather ridiculous. And yet, that is exactly what happened in London just before the world war, a nationwide viral case that ended up to be depicted in The Winslow Boy. The mail order may seem small, and the court proceedings do feel sometimes tedious, but The Winslow Boy shines through its performances, the style, and the insistence to stand up for the truth, even when it means going against societal pressures and hierarchies to have truth recognized.Genre: Drama
Actor: Aden Gillett, Colin Stinton, Gemma Jones, Jeremy Northam, Nigel Hawthorne, Rebecca Pidgeon, Sara Stewart, Sarah Flind
Director: David Mamet
Rating: G

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27. Mansfield Park, 1999

	
While better known for Pride & Prejudice, Emma, and Sense & Sensibility, Jane Austen wrote Mansfield Park, a novel that garnered differing critical interpretations, but still intrigued readers even today. The 1999 film adaptation does capture some of the original novel’s ideas, such as Fanny’s modesty, the Cinderella-like submissiveness as means for survival, and the quiet strength to remain as herself, but it also expands on certain elements that were mostly only alluded to in the original, such as the elements pulled from Jane Austen’s actual life and her own sympathies for anti-slavery. While the film isn’t fully faithful to the original novel and should be considered its own, Mansfield Park does retain some of the essentials that makes it distinctly Austen.Genre: Drama, Romance
Actor: Alessandro Nivola, Amelia Warner, Anna Popplewell, Bruce Byron, Charles Edwards, Danny Worters, Elizabeth Earl, Embeth Davidtz, Frances O'Connor, Gordon Reid, Hannah Taylor-Gordon, Harold Pinter, Hilton McRae, Hugh Bonneville, James Purefoy, Jonny Lee Miller, Justine Waddell, Lindsay Duncan, Philip Sarson, Sheila Gish, Sophia Myles, Victoria Hamilton
Director:  Patricia Rozema
Rating: PG-13

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28. Galaxy Quest, 1999

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, Jerry Penacoli, Joel McKinnon Miller, Jonathan Feyer, 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

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29. The Virgin Suicides, 1999

A group of male friends become obsessed with a group of mysterious sisters who are sheltered by their strict, religious parents after one of them commits suicide. Sofia Coppola does a great job taking the novel and turning it into a full featured movie. The movie is admittedly a bit slow, but it paints such a great picture into the characters lives and everyone around them, that your attention will quickly be turned to that. The casting is spot on and even though it may seem like a very dark subject matter, the film is very enjoyable to watch no matter your taste in movies.

Genre: Drama, Romance

Actor: A.J. Cook, Allen Stewart-Coates, Amos Crawley, Andrew Gillies, Anthony DeSimone, Chelse Swain, Conor Dean Smith, Courtney Hawkrigg, Danny DeVito, Dawn Greenhalgh, François Klanfer, Gary Brennan, Giovanni Ribisi, Hanna Hall, Hayden Christensen, James Woods, Joe Dinicol, Joe Roncetti, John Buchan, Jonathan Tucker, Jonathan Whittaker, Josh Hartnett, Kathleen Turner, Kirsten Dunst, Kristin Fairlie, Leslie Hayman, Melody Johnson, Michael Paré, Michael Pare, Michèle Duquet, Murray McRae, Neil Girvan, Noah "40" Shebib, Robert Schwartzman, Roberta Hanley, Sally Cahill, Sandi Stahlbrand, Scot Denton, Scott Glenn, Sherry Miller, Suki Kaiser, Thomas Mars, Timothy Adams, Tracey Ferencz, Хейден Кристенсен

Director: Sofia Coppola

Rating: R

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