25 Movies Like When Harry Met Sally... (1989)

Staff & contributors

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

Being an intimate, black-and-white portrayal of just two people, it is worth mentioning the two leads in the very first sentence: Blue Jay stars the incredibly versatile Sarah Paulson, who most of you will know from her depiction of Marcia Clark in The People vs. O.J., and Mark Duplass from Creep. In this incredibly intricate dialogue-driven drama, he is of course named Jim, a regular guy with some issues, who runs into his high-school sweetheart Amanda at the grocery store. She is only in town briefly because her sister is having a baby. Amanda agrees to have coffee with him, later they get beer and jellybeans, and find themselves recreating silly tapes at his late mother's house that they use to make when they were still at school. This could quickly become a soppy affair if it wasn't for the heart-felt realness of the acting, for lack of a better term, and all the fine details that the two leads bring to the screen. The chemistry between them is something to behold!

Genre: Drama, Romance

Actor: Alex Lehmann, Clu Gulager, James Andrews, Mark Duplass, Sarah Paulson

Director: Alex Lehmann, Alexandre Lehmann

Rating: Not Rated, Unrated

Sisters Martine and Filippa, daughters of a founder of a religious sect, live a simple and quiet life in a remote coastal village in Denmark. Throughout the course of their lives, they reject possible romances and fame as part of their commitment to deny earthly attachments. This is upended by the sudden arrival of a French immigrant named Babette, who served as their house help to escape the civil war raging in her country.

Babette’s Feast is an inquiry into simplicity and kindness, and whether these would be sufficient to achieve a life of contentment. The religious undertones perfectly fit with the film’s parable-like structure, where bodily and spiritual appetites are satisfied through a sumptuous feast of love, forgiveness, and gratitude.

Genre: Comedy, Drama

Actor: Asta Esper Hagen Andersen, Axel Strøbye, Bendt Rothe, Bibi Andersson, Birgitte Federspiel, Bodil Kjer, Cay Kristiansen, Ebbe Rode, Else Petersen, Finn Nielsen, Gert Bastian, Ghita Nørby, Ghita Nørby, Holger Perfort, Jarl Kulle, Jean-Philippe Lafont, Lars Lohmann, Lisbeth Movin, Pouel Kern, Preben Lerdorff Rye, Stéphane Audran, Stéphane Audran, Therese Hojgaard Christensen, Thomas Antoni, Vibeke Hastrup, Viggo Bentzon

Director: Gabriel Axel

Rating: G

The Fabelmans is often described as director Steven Spielberg’s semi-autobiographical movie about his inauguration into filmmaking, and while it certainly is that, I’d venture to say that it also functions as a universal coming-of-age tale, with protagonist and Spielberg stand-in Sammy Fabelman (Gabriel LaBelle) learning harsh truths about identity, family, and passion for the first time.

Here, we see how so much of filmmaking is intertwined with his life, and how the movies inspire his personality (and vice versa). Whether you’re a fan of Spielberg or not, this movie will surely win you over with its beautiful imagery, impressive technique, and big, big heart.

Genre: Comedy, Drama

Actor: Adriel Porter, Alejandro Fuenzalida, Alex Quijano, Alina Brace, Ari Davis, Art Bonilla, Brinly Marum, Cameron Hennings, Carlos Javier Castillo, Chandler Lovelle, Chloe East, Cody Mitchell, Connor Trinneer, Cooper Dodson, Crystal the Monkey, David Lynch, Ezra Buzzington, Gabriel Bateman, Gabriel LaBelle, Greg Grunberg, Gustavo Escobar, Harper Dustin, Isabelle Kusman, James Urbaniak, Jan Hoag, Jared Becker, Jeannie Berlin, Jonathan Moorwood, Judd Hirsch, Julia Butters, Julyah Rose, Kalama Epstein, Keeley Karsten, Kendal Evans, Lane Factor, Larkin Campbell, Mason Bumba, Max David Weinberg, Meredith VanCuyk, Michelle Williams, Nicolas Cantu, Oakes Fegley, Orion Hunter, Paige Locke, Paul Dano, Rob Shiells, Robin Bartlett, Sam Rechner, Seth Rogen, Sophia Kopera, Stephen Matthew Smith, Taylor Hall, Tia Nalls, Trang Vo, Vera Myers

Director: Steven Spielberg

Rating: PG-13

Strictly Ballroom is an energetic, fun and hilarious movie. Baz Lurhman does an incredible job telling the story of a rebellious young dancer who just wants to dance his own steps in the face of conformity. When he finds an inexperienced yet determined dance partner it's the beginning of an unexpected love story like no other. This movie isn't like the usual rom-com, it has colour, vitality and passion. It's a Moulin Rouge but with even more character, and the work that put Lurhman on the map for everyone.

Genre: Comedy, Drama, Romance

Actor: Antonio Vargas, Armonia Benedito, Barry Otto, Bill Hunter, Gia Carides, John Hannan, Kris McQuade, Lauren Hewett, Pat Thomson, Paul Bertram, Paul Mercurio, Peter Whitford, Pip Mushin, Sonia Kruger, Steve Grace, Tara Morice, Todd McKenney

Director: Baz Luhrmann, Baz Lurhman

Rating: PG

A marvelous combination of perfect casting and a sizzling script. William Hurt, Albert Brooks, and Holly Hunter are such natural talents they could make reading a dictionary watchable, but seeing them weave through James L Brooks punchy dialogue is a delight to behold. The three form the foundation of this drama that is as much about journalistic ambition as it is about love.

Hunter and Brooks are principled workaholics at a news station juggling a platonic friendship that seems destined for more but lacks a driving spark. Enter Hurt, a charming though self-admittedly stupid news anchor, who Hunter at once resents and yet can’t help falling for. What seems like a ready-built rom-com plot, however, churns into something else entirely. It’s a delicious film crackling with wit and character and is as funny as it is astute. 

Genre: Comedy, Drama, Romance

Actor: Albert Brooks, Amy Brooks, Christian Clemenson, Ed Wheeler, Frank Doubleday, Gennie James, Gerald F. Gough, Gerard Ender, Glen Roven, Holly Hunter, Jack Nicholson, Joan Cusack, John Cusack, Kimber Shoop, Leo Burmester, Lois Chiles, Luis Valderrama, Marc Shaiman, Marita Geraghty, Martha Smith, Nat Benchley, Peggy Pridemore, Peter Hackes, Raoul N. Rizik, Richard Thomsen, Robert Katims, Robert Prosky, Robert Walsh, Stephen Mendillo, William Hurt

Director: James L. Brooks

In this romance from 1997, a photographer and a poet meet in an upscale nightclub in Chicago.

They quickly get together and connect on music, poetry, and photography, but Nina, the photographer, decides to go to New York to mend her relationship with her ex-fiance.

It’s so well-acted, funny, and because it’s been enough time that this has become noticeable, a great depiction of big-city life in the 90s. There is smoking inside, riding a motorcycle without helmets, and top-notch fashion.

The producers said they wanted to make “a contemporary film about African-American life that did not deal with guns and drugs,” and probably because they didn’t make compromises, the film was a commercial failure. In recent years, however, it has been quietly growing into a cult classic.

Genre: Comedy, Drama, Romance

Actor: Bernadette Speakes, Bill Bellamy, Isaiah Washington, Khalil Kain, Larenz Tate, Leonard Roberts, Lisa Nicole Carson, Marie-Françoise Theodore, Nia Long

Director: Theodore Witcher

The '80s saw an influx of coming-of-age dramas, with John Hughes’ “Brat Pack” films reigning supreme. For better or worse, their most iconic scenes are embedded in pop culture, like students dancing in detention in The Breakfast Club or Sixteen Candles’ belated birthday cake. Perhaps the most iconic '80s movie moment comes not from Hughes, but from Cameron Crowe’s Say Anything…: Lloyd Dobler (John Cusak) in a trenchcoat, blue Malibu parked behind him, boombox raised over his head in defiant loyalty.

On their last day of high school, Lloyd Dobler resolves to ask out the class valedictorian Diane Court (Ione Skye). Their summer-long relationship is awkward, intense, tender—and familiar to anyone who has ever opened themselves up to falling in love. Say Anything… emotionally outclasses its contemporaries, as Crowe’s writing lends itself to two authentic characters fleshed out beyond caricatures. And as Lloyd crushes hard on Diane, it’s hard not to feel like you’re falling in love with each of them, too.

Genre: Comedy, Drama, Romance

Actor: Amy Brooks, Bebe Neuwirth, Bill Stevenson, Chynna Phillips, Dan Castellaneta, Don Wilson, Eric Stoltz, Glenn Walker Harris Jr., Gloria Cromwell, Gregory Sporleder, Ione Skye, Jason Gould, Jeremy Piven, Jerry Ziesmer, Jim Ladd, Joan Cusack, Joanna Frank, John Cusack, John Hillner, John Mahoney, Johnny Green, Jonathan Chapin, Judy Prescott, Kim Walker, Lili Taylor, Lisanne Falk, Lois Chiles, Loren Dean, Montrose Hagins, Pamela Adlon, Patrick O'Neill, Philip Baker Hall, Polly Platt, Richard Portnow, Stephen Shortridge, Stone Gossard

Director: Cameron Crowe

Muriel is a young social outcast who spends her time obsessively planning a dream wedding without ever having been on a date. Her life is flipped upside down when she steals $15,000 from the family business to go on a tropical getaway. This brilliant comedy is memorable as much for Toni Collete’s breakout role as it is for its snarky subversion of rom-com tropes.

Muriel’s Wedding arrived in a wave of bright and brash Australian comedies of the early 90s like Priscilla Queen of the Desert and Strictly Ballroom. And like these counterparts, its heightened reality gives way to a surprising and heartbreaking emotional core. Director PJ Hogan would go on to direct My Best Friend’s Wedding - a fun but watered-down imitation of the surprising storytelling that made this a cult classic.

Genre: Comedy, Drama, Romance

Actor: Annie Byron, Barry Crocker, Basil Clarke, Belinda Jarrett, Bill Hunter, Cecily Polson, Chris Haywood, Dan Wyllie, Daniel Hepner, Daniel Lapaine, Darrin Klimek, Di Smith, Frankie Davidson, Fred Rouady, Gabby Millgate, Geneviève Picot, Gennie Nevinson, Heather Mitchell, Ineke Rapp, Jacqueline Linke, Jeanie Drynan, John Gaden, John Walton, Jon-Claire Lee, Julian Garner, Kevin Copeland, Kirsty Hinchcliffe, Kuni Hashimoto, Louise Cullen, Matt Day, Nathan Kaye, Penne Hackforth-Jones, Pippa Grandison, Rachel Griffiths, Richard Carter, Richard Morecroft, Richard Sutherland, Rob Steele, Robert Alexander, Robyn Pitt Owen, Roz Hammond, Scott Hall-Watson, Sophie Lee, Susan Prior, Toni Collette, Vincent Ball

Director: P.J. Hogan

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

A Room with a View is downright beautiful. Amidst the impressionistic scenery of Florence’s and England’s countrysides, paired with iconic classical opera, some of Britain’s best actors bare the feelings of their snobbish, upper-class characters in stylish and historically-accurate costumes. But all of these elements aren’t just silly decorations. Like the novel it’s based on, the characters’ refined and respectable veneer, and their insistence on propriety, is a front that hides the feelings stirring in their gut, particularly that of the lovers George Emerson (Julian Sands) and Lucy Honeychurch (Helena Bonham Carter). Inevitably, these feelings can’t be contained– they can only be examined. And when Emerson earnestly declares his love, it’s so powerful to be seen as one’s self rather than as decoration.

Genre: Drama, Romance

Actor: Amanda Walker, Daniel Day-Lewis, Denholm Elliott, Fabia Drake, Helena Bonham Carter, Isabella Celani, James Wilby, Joan Henley, Judi Dench, Julian Sands, Kitty Aldridge, Luigi Di Fiore, Maggie Smith, Matyelok Gibbs, Mia Fothergill, Patricia Lawrence, Patrick Godfrey, Peter Cellier, Peter Munt, Rosemary Leach, Rupert Graves, Simon Callow

Director: James Ivory

Rating: Not Rated

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

Far from feeling like English literature homework, this version of Shakespeare’s romantic comedy of errors fizzes with vitality and wit. Kenneth Branagh directs and stars in his own sumptuous adaptation, which also features a banquet of dashing talent in their prime, including Emma Thompson and a winning Denzel Washington.

Even amongst the film’s superlative ensemble (which also features a melodramatically villainous Keanu Reeves and Michael Keaton as a farcically inept policeman), Thompson stands out for her instinctive grasp of Shakespeare’s genius and easy ability to lift it off the page and give it sparkling life. As Beatrice, she deals out wry cut-downs of Branagh’s vain Benedick, all while trying to suppress the roiling romantic tension that nevertheless persists between them. It might not be set to the music of ABBA, but with Patrick Doyle’s radiant score, an intoxicatingly beautiful Tuscan setting, and an infectious, non-stop party vibe, the joyous Much Ado About Nothing feels more akin to Mamma Mia than any of cinema’s other Shakespeare adaptations.

Genre: Comedy, Drama, Romance

Actor: Alex Lowe, Andy Hockley, Ben Elton, Brian Blessed, Chris Barnes, Conrad Nelson, Denzel Washington, Edward Jewesbury, Emma Thompson, Gerard Horan, Imelda Staunton, Jimmy Yuill, Kate Beckinsale, Keanu Reeves, Kenneth Branagh, Michael Keaton, Patrick Doyle, Phyllida Law, Richard Briers, Richard Clifford, Robert Sean Leonard

Director: Kenneth Branagh

Jenna is a young woman living a rather unhappy life in a town in the American South. The highlight of her days is inventing and baking pies at the diner where she works, giving them names like the “I Hate My Husband Pie”. Her life, however, seems to have hit an unpleasant dead-end: as her pie suggests, she no longer loves her chauvinistic pig of a husband and, as if that wasn’t enough, she’s pregnant with his child.

Waitress is about one woman’s determination to dig through the sourness of life in the hopes of finding a layer of sweetness underneath. Premiering only months after lead actress Adrienne Shelly’s tragic death at the age of 40, Waitress features wonderful performances that make for a delicious film, with the right ingredients to hold everything together.

Genre: Comedy, Drama, Romance

Actor: Adrienne Shelly, Andy Griffith, Andy Ostroy, Caroline Fogarty, Cheryl Hines, Christy Taylor, Cindy Drummond, Darby Stanchfield, Eddie Jemison, Heidi Sulzman, Jeremy Sisto, Keri Russell, Lauri Johnson, Lew Temple, Mackenzie King, Nathan Dean, Nathan Fillion, Sarah Hunley

Director: Adrienne Shelly