5 Movies Like Cruel Intentions (1999)

Chasing the feel of watching Cruel Intentions ? Here are the movies we recommend you watch right after.

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1. Election, 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, Romance

Actor: B.J. Tobin, Chris Klein, Colleen Camp, Delaney Driscoll, Frankie Ingrassia, Holmes Osborne, Jason Paige, Jeanine Jackson, Jessica Campbell, John Ponzio, Kaitlin Ferrell, 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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2. King of Devil's Island, 2011

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

3. Secretary, 2002

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: Amy Locane, Ezra Buzzington, James Spader, Jeremy Davies, Jessica Tuck, Julene Renee, Lacey Kohl, Lauren Cohn, Lesley Ann Warren, Lily Knight, Maggie Gyllenhaal, Mary Joy, Michael Mantell, Osgood Perkins, Oz Perkins, Patrick Bauchau, Sabrina Grdevich, Stephen McHattie

Director: Steven Shainberg

Rating: R

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4. Pieces of April, 2003

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., John Gallagher Jr., Katie Holmes, Leila Danette, Lillias White, Oliver Platt, Patricia Clarkson, Rusty De Wees, Sally Leung Bayer, Sean Hayes, Sisqó, Susan Bruce, Vitali Baganov

Director: Peter Hedges

Rating: PG-13

5. Pleasantville, 1998

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, Danny Strong, Dawn Cody, Denise Dowse, Don Knotts, Giuseppe Andrews, J.T. Walsh, Jane Kaczmarek, Jason Behr, Jeff Daniels, Jenny Lewis, Joan Allen, John Ganun, Justin Nimmo, Kai Lennox, Kevin Connors, Lela Ivey, Maggie Lawson, Marc Blucas, Marissa Ribisi, Marley Shelton, McNally Sagal, Natalie Ramsey, Paul Morgan Stetler, Paul Walker, Reese Witherspoon, Tobey Maguire, William H. Macy

Director: Gary Ross

Rating: PG-13

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