7 Best Movies & Shows Released in 1999 On Cineplex Canada

Staff & contributors

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

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, 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, 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

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, 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

Director: Kimberly Peirce

Rating: R

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

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

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, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

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

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