8 Best Movies & Shows Released in 1999 On Max (HBO Max)

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

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, Henry Silva, Isaach De Bankolé, Jamie Hector, John Tormey, Jonathan Teague Cook, José Rabelo, Joseph Rigano, Renee Bluestone, Richard Portnow, Roberto Lopez, RZA, Sharon Angela, Tracy Howe, Tricia Vessey, Victor Argo, Vince Viverito, Vinny Vella

Director: Jim Jarmusch

Rating: R

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, Frédéric Bodson, Mireille Bailly, Olivier Gourmet

Director: Jean-Pierre Dardenne, Luc Dardenne

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, 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

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

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, John Comerford, 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, David Neville, 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, Kate Doherty, Katrin Cartlidge, 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, Monica Dolan, Naoko Mori, Nicholas Boulton, Nicholas Woodeson, Nick Bartlett, Paul Barnhill, Paul Rider, 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, Barbara George-Reiss, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Kinna McInroe, Kyle Scott Jackson, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, Richard Riehle, Ron Livingston, Rupert Reyes, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R