8 Movies Like Secretary (2002)

Staff & contributors

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

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.

Written and directed by Academy-Award-winning Kenneth Lonergan (Manchester by the Sea, Gangs of New York), you can certainly count on the qualities of this subtle, beautiful, and moving drama about two siblings growing apart and reuniting later in life.

An Academy-Award-nominated Laura Linney plays Sammy, a single mother in a small town who is extremely protective of her 8-year-old son. When her younger and somewhat troubled brother Terry (played by the ever-reliable Mark Ruffalo) visits her out of the blue, Sammy has to deal with a slew of contradicting emotions towards her brother, whose appearance threatens to upend her life as she knew it.

Straight, thoughtful, and beautifully crafted, You Can Count on Me is an honest and genuine exploration of unconditional love in celluloid form. Think of it as much more hopeful The Skeleton Twins.

Genre: Drama, Family

Actor: Adam LeFevre, Amy Ryan, Betsy Aidem, Gaby Hoffmann, Halley Feiffer, J. Smith-Cameron, Jon Tenney, Josh Lucas, Kenneth Lonergan, Laura Linney, Lisa Altomare, Mark Ruffalo, Matthew Broderick, Michael Countryman, Nina Garbiras, Rory Culkin, Whitney Vance

Director: Kenneth Lonergan

Rating: R

Robert Downey Jr's triumphant return to film, this movie is a satirical take on film noir and detective movies in general. The screen chemistry between Gay Perry the private eye, played by Val Kilmer, and Downey Jr's robber turned actor, Harry Lockhart, is hysterical, and the film's tongue in cheek nature is witty, smart, and delivers. Directed by the man who directed Lethal Weapon, the action is top notch, the laughs are pretty much constant, and the mystery is compelling. It's mind boggling that nobody saw this when it came out.

Genre: Action, Comedy, Crime, Mystery, Thriller

Actor: Ali Hillis, Angela Lindvall, Ariel Winter, Ben Hernandez Bray, Bill McAdams Jr., Brendan Fehily, Brian Simpson, Cole S. McKay, Corbin Bernsen, Daniel Browning Smith, Dash Mihok, David Newsom, Evan Parke, Harrison Young, Indio Falconer Downey, Jake McKinnon, Joe Keyes, Josh Richman, Judie Aronson, Kathy Lamkin, Larry Miller, Laurence Fishburne, Lela Edgar, Martha Hackett, Michelle Monaghan, Nancy Fish, Robert Downey Jr., Rockmond Dunbar, Saida Pagan, Shannyn Sossamon, Stephanie Pearson, Tanja Reichert, Teresa Maria Herrera, Val Kilmer, Vincent Laresca, Wiley M. Pickett

Director: Shane Black

Rating: R

A very intelligent and nuanced movie that relentlessly asks unpleasant questions. It's a story about a woman seeking freedom by turning away from her own family and finding something she did not expect. The main character of the movie, Martha, is taken in by a cult and the movie depicts how this experience shapes and warps her life, thoughts, and actions. The time she spent with the cult ultimately also shapes her own personality, which raises questions about her identity and the place she now fits in. Every actor is well cast, and especially Elizabeth Olsen (playing Martha) puts on a stand-out performance, which proves that she is an actor to watch out for in the years to come.

Genre: Drama, Mystery, Thriller

Actor: Adam David Thompson, Allen McCullough, Brady Corbet, Christopher Abbott, Elizabeth Olsen, Gregg Burton, Hugh Dancy, John Hawkes, Julia Garner, Lauren Molina, Louisa Krause, Maria Dizzia, Sarah Paulson, Tobias Segal

Director: Sean Durkin

Rating: R

This is a touching saga based on the plight of the women labelled as "fallen" that the Magdalene Laundries housed in Ireland. The movie grips you by the throat right from the first minute and the sense of injustice to women that characterizes the entire length of the film only rarely eases up to give you room to appreciate the emotional complexities that each individual character represents. The stories of Margaret, Bernadette and Rose and the people they meet inside the Magdalene Laundry will force you to ask time and again during the movie, "Why?" and "Who are they to?". You will share in Bernadette's sense of outrage, in Rose's compassion and Margaret's acute fear of the church, of speaking up and asking for justice. So much so, that you may even find yourself identifying with (or at least understanding) Crispina's questionable grasp on reality. Worst of all, the devout Catholic establishment that this was, hypocrisy and corruption ran through its every vein, adding to the shock and resentment that builds towards the, for the lack of a better word, captors of our protagonists. The Magdalene Sisters is a tribute to one of the forgotten chapters in a long history of injustice to women and an absolutely moving one at that. It does not fail to utterly horrify while it also warms your heart.

Genre: Drama, History

Actor: Anne-Marie Duff, Britta Smith, Chris Patrick-Simpson, Daniel Costello, Dorothy Duffy, Eamonn Owens, Eileen Walsh, Eithne McGuinness, Frances Healy, Geraldine McEwan, Mary Murray, Nora-Jane Noone, Peter Mullan, Phyllis MacMahon, Stephen McCole

Director: Peter Mullan

Rating: R

Eat Drink Man Woman takes place in Taipei, Taiwan in the mid-1990s. It tells the story of an aging father and his three daughters, all of whom are navigating different phases of adulthood while embracing new relationships. The family uses cooking and eating together as a way to communicate their love.

Food as a love language wasn’t a new concept in 1994, when the film was released, however it is impeccably explored in Eat Drink Man Woman. 

Genre: Comedy, Drama, Romance

Actor: Chen Chao-jung, Chi-Der Hong, Chin-Cheng Lu, Gin-Ming Hsu, Gua Ah-leh, Huel-Yi Lin, Jui Wang, Kuei-Mei Yang, Lester Chan, Lester Chit-Man Chan, Lung Hsiung, Lung Sihung, Shih-Jay Lin, Sihung Lung, Sylvia Chang, Wang Yu-wen, Winston Chao, Wu Chien-Lien, Ya-lei Kuei, Yang Kuei-Mei, Yu Chen, Yu-Wen Wang, 张艾嘉

Director: Ang Lee

Rating: Not Rated

Remarkably, Steven Soderbergh was only 26 years old when he directed this coolly assured debut, the searingly candid script of which he also wrote in just eight days. Despite the pornographic implications of its title, this is more concerned with exploring whether honesty — not sex — is the means to real intimacy. In fact, the only nakedness glimpsed here is of the emotional kind, as twenty-something drifter Graham’s (James Spader) total aversion to lying has an infectious influence on everyone around him.

The primary recipient of that disarming effect is Ann (Andie MacDowell), the wife of Graham’s old college buddy who is blasé about sex and neurotic about everything else. Talking to Graham has a therapeutic effect on her, but he takes something else away from conversation: chronically impotent, he simulates the sexual experience by conducting erotically themed interviews with women on videotape. Preferring to sublimate his desires through his camcorder, Spader’s physically aloof character is a disturbingly prescient one for what it suggested then about technology’s future impact on human relationships. That Soderbergh managed to conduct such a complex psychosexual drama all through dialogue — on his first feature, no less — makes him exceedingly worthy of the record this earned him of the youngest solo Palme d’Or-winning director ever.

Genre: Drama

Actor: Alexandra Root, Andie MacDowell, David Foil, Earl T. Taylor, James Spader, Laura San Giacomo, Peter Gallagher, Ron Vawter, Steve Brill, Steven Brill

Director: Steven Soderbergh

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

Written and directed by the film’s star, Albert Brooks, Defending Your Life imagines an afterlife in which purgatory is a courtroom, and whether you’ll be saved or damned is judged based on the life you led on Earth.

Did you live courageously, or did you live fearfully? Were you ashamed, meek, afraid of being vulnerable? Or did you risk some tender part of yourself in order to connect with others, to meaningfully impact another life?

Daniel Miller (Brooks) discovers he may not have lived as boldly as he assumed. In the afterlife and awaiting his day in afterlife court, he meets Julia (Meryl Streep, in what is possibly one of her most captivating roles), who is kind and thoughtful and a capital-G Good person. Of course, it’s only after dying that Daniel tunes in to the great possibility of a life not lived on autopilot. But is he too late to atone for his unexamined life—or is there time yet for a second chance?

Genre: Comedy, Drama, Fantasy, Romance

Actor: Albert Brooks, Alex Sheafe, Arell Blanton, Art Frankel, Bob Braun, Buck Henry, Cathleen Chin, Clarke Coleman, Clayton Norcross, Clifford Einstein, David Purdham, Ernie Brown, Ethan Embry, Gary Ballard, Gary Beach, George D. Wallace, George Wallace, Glen Chin, Greg Finley, Hal Landon Jr., Ida Lee, James Eckhouse, James Paradise, Jennifer Barlow, Jennifer Barlow Grodsky, Jerry Prell, Jim McKrell, Joey Miyashima, Julie Cobb, Ken Thorley, Kristopher Kent Hill, Lee Grant, Leonard O. Turner, Lillian Lehman, Marilyn Rockafellow, Mary Pat Gleason, Maxine Elliott Hicks, Meryl Streep, Michael Durrell, Newell Alexander, Noley Thornton, Nurit Koppel, Peter Schuck, Rachel Bard, Raffi Di Blasio, Rip Torn, Roger Behr, Ronald L. Colby, S. Scott Bullock, Sage Allen, Shirley MacLaine, Sidney Chankin, Susan Walters, Time Winters, Wil Albert

Director: Albert Brooks