3 Movies Like Road Trip (2000)

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

Already featuring some of the desperation and melancholy that would go on to characterize most of his work, Paul Thomas Anderson's Hard Eight manages to draw palpable suspense and drama out of, essentially, three characters and a couple of seedy locations. We learn perhaps too little about these characters and why this veteran gambler is drawn to a young homeless man, but there's also something intriguing about how Anderson suggests much larger and much crueler stories going on just out of sight. It truly feels like these people are just trying to hold on to the smallest things that ease their pain—which works because of incredibly compelling work from Philip Baker Hall, John C. Reilly, and a young Gwyneth Paltrow already at the top of her game.

Genre: Crime, Drama

Actor: Ernie Anderson, F. William Parker, Gwyneth Paltrow, Jake Cross, John C. Reilly, Kathleen Campbell, Melora Walters, Nathanael Cooper, Philip Baker Hall, Philip Seymour Hoffman, Renee Breen, Richard Gross, Robert Ridgely, Samuel L. Jackson, Wendy Weidman, Wynn White

Director: Paul Thomas Anderson