4 Movies Like When Harry Met Sally... (1989) On Tubi

Staff & contributors

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, 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, 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

It’s easy enough to pitch Moonstruck with the promise of Cher and a young Nicolas Cage getting hot and heavy in 80s New York, but it’s so much more than its two outsized leads. Loretta (Cher) is on track to marry Johnny (Danny Aiello) when he tasks her with inviting his brother Ronny (Nicolas Cage) to their wedding. Before long Loretta and Ronny are having a whirlwind affair that threatens to derail everything. 

Despite the somewhat risque premise, Moonstruck is a lighthearted, sentimental, romance fit for the holidays. A big cast playing the warm-hearted family rounds things out, and some of the best moments are digressions that explore the romantic entanglements outside of the central couple.  At times Moonstruck feels a bit too big, too over-the-top, too cheesy, but it’s a New York slice cheesy, it’s a ‘That’s Amore’ cheesy, it’s a cheesy that tucks you in at night after a  helping of manicotti and a big bottle of wine.

Genre: Comedy, Drama, Romance

Actor: Al Therrien, Amy Aquino, Anita Gillette, Ann McDonough, Antonia Minella, Betty Orsatti, Catherine Scorsese, Cathy Ladman, Charles Scorsese, Cher, Curt Hayward, Cynthia Dale, Danny Aiello, David S. Howard, Feodor Chaliapin Jr., Frank Gio, Gina DeAngeles, Helen Hanft, Joe Grifasi, John Christopher Jones, John Mahoney, Julie Bovasso, Leonardo Cimino, Lisa Howard, Lou Pitoscia, Louis Di Bianco, Louis Guss, Matt Myers, Mimi Lizio, Nada Despotovich, Nicholas Pasco, Nicolas Cage, Olympia Dukakis, Paul Benedict, Paula Trueman, Peter Austin Noto, Robert Weil, Robin Bartlett, Sonny Bono, Stephany Hitchcock, Tim Koetting, Tommy Hollis, Tony Azito, Vincent Gardenia

Director: Norman Jewison

This quirky 1988 adventure drama is newly available on Amazon Prime. It’s the classic that never was, the story of a rundown gas station motel in the Southern US where a lonely West German lady called Jasmin Munchgstettner ends up by accident.

The owner of the operation, a short-tempered woman by the name of Brenda, doesn’t really take to Jasmin. However, the longer the West German guest stays at the motel, the more a friendship forms between the two.

Genre: Comedy, Drama

Actor: Alan S. Craig, Apesanahkwat, CCH Pounder, Christine Kaufmann, Darron Flagg, G. Smokey Campbell, Gary Lee Davis, George Aguilar, Hans Stadlbauer, Jack Palance, Marianne Sägebrecht, Mark Daneri, Monica Calhoun, Ray Young, Ronald Lee Jarvis

Director: Percy Adlon

Rating: PG