7 Movies Like Cruel Intentions (1999)

Staff & contributors

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

This gorgeous Scandinavian movie is based on a true story and stars the ever-reliable Stellan Skarsgard. He plays the governor of a strict youth correctional facility in Norway in 1915. The arrival of a feared kid kickstarts events that are very famous in Norway but little-known elsewhere: an uprising within the facility that will eventually require the army to get involved. A strong movie with stellar (Stellan) performances.

Genre: Action, Drama

Actor: Benjamin Helstad, Ellen Dorrit Petersen, Frank-Thomas Andersen, Kimmo Rajala, Kristoffer Joner, Magnar Botten, Martin Slaatto, Per Gørvell, Stellan Skarsgård, Trond Nilssen

Director: Marius Holst

Rating: Not Rated

Running on Empty is a movie that covers many timely themes including capitalism, education, and social class. It tells the story of a family who have to go on the run and hide their true identity for the rest of their lives. Director Sidney Lumet’s light touch on heavy topics gives the movie a tender and intimate atmosphere throughout. Aside from the great script, River Phoenix's performance is definitely one of the biggest highlights of this movie, where he successfully delivers a restrained yet fascinating performance. Christine Lahti and Judd Hirsch also give a top-notch performance that adds to the movie’s thrill. In short, Running on Empty is the kind of movie that shows there is courage in running away when it's the right thing to do.

Genre: Crime, Drama, Romance

Actor: Alice Drummond, Angela Pietropinto, Augusta Dabney, Bobo Lewis, Burke Pearson, Christine Lahti, Daniel Dassin, David Margulies, Donna Hanover, Ed Crowley, Elżbieta Czyżewska, Herb Lovelle, Jenny Lumet, Jonas Abry, Judd Hirsch, Justine Johnston, L.M. Kit Carson, Leila Danette, Lynne Thigpen, Marcia Jean Kurtz, Martha Plimpton, Michael Boatman, River Phoenix, Ronnie Gilbert, Sloane Shelton, Steven Hill, William Foeller

Director: Sidney Lumet

Rating: PG-13

Lee Holloway (Maggie Gyllenhaal) is compassionate and diminutive, but her social awkwardness hinders her as she attempts to navigate young adulthood. After recently being hospitalized for self-harm, Lee is determined to prove she is capable of autonomously taking care of herself. She begins working as a secretary for E. Edward Grey (James Spader), a meticulous attorney.

It’s not long before both Lee and Edward realize they’re attracted to one another’s opposite natures: Lee’s obedience and Edward’s dominance. They begin a mutually consensual BDSM relationship, with both experiencing a sexual and emotional awakening. 

The premise may sound familiar: 50 Shades of Grey is widely acknowledged as, at the very least, owing its title to Secretary. But while 50 Shades of Grey portrays an unhealthy, toxic, and superficial idea of a BDSM affair, Secretary maintains that consent must be at the core of any relationship. And ultimately for Lee and Edward, BDSM becomes a way for them to communicate and overcome their individual pain, and unite stronger as a vulnerable, loving whole.

Genre: Comedy, Drama, Romance

Actor: Alison Tatlock, Amy Locane, Christina Gray, David Wiater, Diane McGee, Erin Cressida Wilson, Ezra Buzzington, Herbert Russell, James Spader, Jeremy Davies, Jessica Tuck, Julene Renee, Kyle Colerider-Krugh, Lacey Kohl, Lauren Cohn, Lesley Ann Warren, Lily Knight, Maggie Gyllenhaal, Mary Joy, Michael Mantell, Osgood Perkins, Oz Perkins, Patrick Bauchau, Sabrina Grdevich, Shannon Convery, Stephen McHattie, Steven Fierberg, Steven Shainberg

Director: Steven Shainberg

Rating: R

The entirety of Pieces of April takes place on Thanksgiving Day, a busy holiday meant to bring loved ones together. Sure enough, April, the eldest Burns daughter, takes great pains to prepare a nice dinner for her visiting family. But we soon learn that she is motivated less by excitement than by dread: she's long been estranged, disowned even, by her uptight mother, Joy, who is only agreeing to come because she's sick with cancer. April seems to be on a reluctant mission to fix their fraught relationship, but pesky (albeit funny) mishaps, both on her and Joy's end, keep getting in the way. 

Shot digitally and very closely with hand-held cameras, Pieces of April looks as intimate as it feels. It's a snapshot of an era and of a particular family dynamic, one that relatably relies on both love and scorn to keep going. It's an excellent, honest, and underrated gem of a movie.

Genre: Comedy, Drama, Family

Actor: Adrian Martinez, Alice Drummond, Alison Pill, Anney Giobbe, Armando Riesco, Birdie M. Hale, Derek Luke, Isiah Whitlock Jr., Jamari Richardson, John Gallagher Jr., Katie Holmes, Leila Danette, Lillias White, Oliver Platt, Patricia Clarkson, Rusty De Wees, Sally Leung Bayer, Sean Hayes, Sisqó, Stephen Chen, Susan Bruce, Vitali Baganov

Director: Peter Hedges

Rating: PG-13

Narrated by the familiar voice of Jack Black, Apollo 10 ½ is a throwback story told with admirable specificity and imagination. Black plays a grown-up Stan, who looks back on his younger years with a mix of fondness and wonder: how did they get away with the things they did then? American suburbia in the 1960s was both loose and conservative, caught between a generation holding on to the reins of the earlier century and one eager to launch into the next. 

Stan, as the youngest child of a big, rowdy family, gives us a charming look into the times, as well as a projection of his own fascination: Apollo 11 and the space age. He inserts himself in this monumental narrative and generously brings us along in his fantasy. Sometimes it’s hard to tell whether Stan’s recruitment by NASA is actually fact or fiction, but that’s part of the fun, especially since Stan himself doesn’t seem to mind at all.

Genre: Adventure, Animation, Comedy, Drama, Family, History, Sci-Fi & Fantasy, Science Fiction

Actor: Bill Wise, Brent A. Riggs, Brian Villalobos, Buzz Aldrin, Christian Moran, David DeLao, Glen Powell, Holt Boggs, Jack Black, Janis Joplin, Jennifer Griffin, Jessica Brynn Cohen, John F. Kennedy, John Kaler, Josh Wiggins, Keslee Blalock, Larry Jack Dotson, Lee Eddy, Milo Coy, Mona Lee Fultz, Natalie L'Amoreaux, Neil Armstrong, Nick Stevenson, Richard Nixon, Samuel Davis, Walter Cronkite, Zachary Levi

Director: Richard Linklater

Rating: PG-13

When David and his sister Jennifer fight over the TV remote, they are suddenly transported to David’s favorite sitcom, Pleasantville. They’re told by a spirit guide that their best bet at getting out is fitting in, but their modern sensibilities prove to be too much for the genteel ‘50s town. Soon, the residents learn about sex, art, criticism, and politics, and it’s up to the twins to control the ensuing mayhem and guide them to the right path. 

In hindsight, Pleasantville seems ahead of its time, preceding Marvel’s WandaVision as the ultimate, deconstructed homage to 20th-century television. But unlike the series, Pleasantville dives deep into personal and social politics, all while maintaining an impressive balance of wisdom and humor. Equally notable is the film’s transformation from black and white to Technicolor, which, aside from being a symbolic and technical feat, is also a piece of pure, mesmerizing cinema.

Genre: Comedy, Drama, Family, Fantasy

Actor: Andrea Baker, Charles C. Stevenson Jr., Danny Strong, David Tom, Dawn Cody, Denise Dowse, Don Knotts, Erik MacArthur, Gerald Emerick, Giuseppe Andrews, J. Patrick Lawlor, J.T. Walsh, James Keane, Jane Kaczmarek, Jason Behr, Jason Maves, Jeanine Jackson, Jeff Daniels, Jenny Lewis, Jim Antonio, Joan Allen, John Ganun, Johnny Moran, Justin Nimmo, Kai Lennox, Kevin Connors, Kristin Rudrüd, Laura Carney, Lela Ivey, Maggie Lawson, Marc Blucas, Marissa Ribisi, Marley Shelton, McNally Sagal, Nancy Lenehan, Natalie Ramsey, Patrick Thomas O'Brien, Paul Morgan Stetler, Paul Walker, Reese Witherspoon, Robin Bissell, Stanton Rutledge, Tobey Maguire, Weston Blakesley, William H. Macy

Director: Gary Ross

Rating: PG-13