The Pen in Hand’s Guide to the Best Valentine’s Day Movies

Illustration by Michael DiMilo

Top Ten Romance Films

By Geoff Carter

It’s Valentine’s Day. Love is in the air, but those of us who choose to enjoy a warm and cozy evening inside, finding that perfect romantic movie is the perfect way to enjoy that special someone. So, rather writing one of my garden variety reviews, I’ve decided to send out a sampler—a box of chocolates, as it were—of film romances for the home viewer to pick and choose from. You’ll never know what you might find. We have a little something for everybody, from the traditional to the alternative, from the romantic to the erotic, the comic to the tragic, and the commonplace to the epic. 

These are excellent movies. Some are probably familiar to you. Some may be a tad too racy for your taste—watch the kids—but every one of them is worth watching. Remember, even though this segment is entitled Love in the Afternoon, feel free to find love anytime.

The Top Ten Romantic Movies


Attribution:
English: “Copyright © 1960 – United Artists Corporation”.
, Public domain, via Wikimedia Commons

The Apartment: Insurance clerk C.C. Baxter (Jack Lemmon) finds a quick way up the corporate ladder by lending out his apartment to executives for their off-hour trysts but finds himself ensnared in his ambitions while sorting out his own love life. Notable for Billy Wilder’s snappy dialogue and outstanding direction. 

Starring: Jack Lemmon, Shirley MacLaine, Fred MacMurray, and Ray Walston.

Available on Prime Video.


Attribution: Mavelus, Public domain, via Wikimedia Commons

Moonstruck: A newly engaged middle-aged woman finds herself in a difficult situation when she falls madly in love with her fiancé’s brother. A full moon in Brooklyn, the Metropolitan Opera in Manhattan, Nicholas Cage in a tuxedo? What could be more romantic? Notable for an outstanding ensemble cast—particularly during the breakfast scene at the Castorini house.  

Starring: Cher, Nicholas Cage, Olympia Dukakis, Vincent Gardenia, and Danny Aiello.

Available on Hulu.


Gregory’s Girl: In this quirky film, a gawky young man falls for a beautiful young soccer player but soon finds himself completely out of his league. Even so, he goes out with her on what turns out to be one of the strangest and most hilarious blind dates in the history of cinema. Notable for the mysterious penguin mascot and the steamy bath dance. 

Starring: John Gordon Sinclair, Dee Hepburn, Claire Grogan, and Bill Greenleaf.

Available for Rental on Prime Video.


Brokeback Mountain: Two cowboys scrabbling to make a living take a long-term job together guarding a flock of sheep on the wilds of Brokeback Mountain where they fall in love. The two continue to meet secretly for years despite complications from friends and families. Notable for Heath Ledger’s brooding and powerful performance. He commands the screen. 

Starring: Heath Ledger, Jake Gyllenhaal, Anne Hathaway, Michelle Williams, and Randy Quaid.

Available on Hulu.


While You Were Sleeping: Turnstile clerk Lucy (Sandra Bullock) pulls the man she has a crush on from the CTA tracks and saves his life, but through a series of misunderstandings his family thinks the two are engaged and treats her as one of their own. While he is in a coma, Lucy discovers what love really is and where it is. Notable for Sandra Bullock’s charming breakout performance. 

Starring: Sandra Bullock, Bill Pullman, Peter Boyle, Peter Gallagher, Jack Warden, Glynis Johns.

Available on Hulu.


Blue is the Warmest Color: A young French girl is drawn to an enigmatic and beautiful young woman with whom she starts a torrid affair. The relationship grows and blossoms as the young women grow into two very different adults. Warning: graphic sexual content. Notable for the incredible performances of the two leads. And we see Lea Seydoux in life before James Bond.

Starring: Lea Seydoux, Adele Exarchopoulos, and Salim Kechiouche.

Available on Prime Video.


Attribution: Mavelus, Public domain, via Wikimedia Commons

Call Me By Your Name: Elio, a teen summering with his family in Europe meets an older graduate student with whom he falls madly in love. While navigating the course of his passion with the older man, Elio discovers how to cope with love, loss, and forgiveness. Notable for an incredible speech about life from the father, played by Michael Stuhlbarg.

Starring: Timothee Chalamet, Armie Hammer, Michael Stuhlbarg, and Amira Casar.

Available for Rent on Prime Video.


Attribution:
FLC001
, Public domain, via Wikimedia Commons

If Beale Street Could Talk: Childhood friends and lovers Tish and Fonny fight to keep their relationship alive through Fonny’s false imprisonment and the impending birth of their first child, mostly through the bonds of love and the strength of their families. Notable for Regina King’s Oscar nominated performance. 

Starring: Kiki Layne, Stephan James, Regina King, and Colman Domingo. Directed by Barry Jenkins. 

Available on Hulu.


The Big Sick: A young Pakistani man struggles to maintain a relationship with his American girlfriend while dealing with the expectations of his own matchmaking family, and then—when his girlfriend falls into a coma—explaining things to her family. Notable for Ray Romano and Holly Hunter’s supporting roles as Emily’s parents. 

Starring: Kumail Nanjiani, Zoe Kazan, Ray Romano, and Holly Hunter. 

Available on Prime Video.


Cold War: A romance set in post World War II Poland and France in which a music director discovers a young singer with whom he falls passionately in love. The film follows their romance during the next twenty years through the twists and turns of European—and personal—politics. Notable for its cinematography, being beautifully shot in black and white.

Starring: Joanna Kulig, Tomasz Kot, Borys Szyc. Directed by Pawel Pawlikowski. 

Available on Prime Video.

Honorable Mention

The Princess Bride

Romeo and Juliet (1996)

Shakespeare in Love

Casablanca

The Umbrellas of Cherbourg

Feel free to add any films I may have missed…