Classic Hollywood is a hotbed of romantic comedies and dramas. Many of the tropes and romantic elements that we today find tried or true were shining new in Hollywood’s adolescence. Provided here are a few of the best classic film romances and it is to be hoped they’ll make your heart happy whether they are shared with a friend, a lover, or just a piece of pie.

Screen capture from Vivacious Lady starring Ginger Rogers and James Stewart

via BBC

Vivacious Lady (1938)

Starring: Ginger Rogers, James Stewart

Gal’s got gumption, option 1. Peter, a mild-mannered botany professor, falls in love with vivacious, Manhattan nightclub singer, Francey. But bringing her home to meet his well-to-do family is sure to cause a stir in their quiet college town.


Screen capture from Ball of Fire starring Barbara Stanwyck and Gary Cooper
via Doctor Marco

Ball of Fire (1941)

Starring: Barbara Stanwyck, Gary Cooper

Gal’s got gumption, option 2. Gangster’s moll, Sugarpuss O’Shea, needs a place to lay low while her mob boss boyfriend, Joe Lilac, is under police investigation. She finds the perfect hideout in the company of research professors, all bachelors, who are compiling an Encyclopedia. An unlikely attraction forms between Sugarpuss and the grammarian professor, Bertram Potts.


Screen capture from The More the Merrier starring Joel McCrea and Jean Arthur
via The Blonde at the Film

The More the Merrier (1943)


Starring: Jean Arthur, Joel McCrea

U.S. Capitol, Washington D.C., suffered a serious housing shortage during the second world war. Apartments were at a premium and part of the “war effort” was sharing space. When Connie decides to sublet her apartment’s second bedroom she has a list of qualifications, chief among them that the new tenant be female. But all that is about to go out the window.


Screen capture from To Have and Have Not starring Lauren Bacall and Humphrey Bogart.

via The Ace Black Blog

To Have and Have Not (1944)

Starring: Lauren Bacall, Humphrey Bogart

This might not be your first thought for romance. The film is based on a Hemingway novel and more focused on wartime espionage but it makes the list for two key reasons. Firstly, it is the film where Bogey & Bacall met and fell in love. Their on-screen chemistry is white-hot and indicative of their growing off-screen romance. Second, it has one of the most salacious lines in film history.

Gif from To Have and Have Not with Lauren Bacall quoting "You know how to whistle, don't you, Steve? You just put your lips together and blow."

via Fragra Greatest Movies 


Screen capture from The Quiet Man starring Maureen O'Hara and John Wayne.

via Breise Bresise Leigh Go Leire

The Quiet Man (1952)

Starring: Maureen O’Hara, John Wayne

John Wayne is better known for his Westerns but there are a handful of films where he isn’t playing a gunslinger. The Quiet Man is one of these. Boxer Sean Thornton has returned to his family’s homestead in Ireland to escape his past in America. As he tries to fit back in to small village life he’ll attempt to win the heart of fiery Mary Kate.

I’d like to make a special note regarding this film because though it has much to love, beautiful cinematography, it also has some strong sexist themes, bordering on abuse. Sean and Mary Kate’s relationship is heated in more ways than one and though Mary Kate often gives as much as she gets there is some rough handling throughout.


Screen capture from Sabrina starring Audrey Hepburn and Humphrey Bogart.

via Filmic Mag

Sabrina (1954)


Starring: Audrey Hepburn, Humphrey Bogart

Sabrina, the daughter of a chauffeur, grew up watching the glamorous lives of the Larrabee family from the apartment over the garage. From a distance, she has pined over the Larrabee’s younger son, David. Though two years away in Paris have altered Sabrina into a sophisticate it has not changed her love for David. Having at last caught David’s eye, Sabrina finds she’s also garnered attention from David’s older brother, Linus.

Screen capture from It Should Happen to You with Jack Lemmon and Judy Hollidayvia Faintly Familiar

It Should Happen to You (1954)

Starring: Judy Holliday, Jack Lemmon

Gladys has always wanted to be famous and decides to fast track the process by renting a billboard to display just her name. Fame quickly follows but the life of celebrity is more than she bargained for.

This is my favorite film. Not of this list – EVER. I don’t pick favorites easily but this film is tops because Holliday and Lemmon are each hilarious in their own right but together they are electric. And, get this, they never kiss, their entire romance is carried in glances and touch and it is still the most romantic film I’ve ever seen.

GIF from It Should Happen to You with Jack Lemmon and Judy Holliday singing a duet of "Let's Fall in Love"

via Clifton Weeb tumblr 

Screen capture from An Affair to Remember starring Cary Grant and Deborah Kerrvia IMDB

An Affair to Remember (1957)

Starring: Deborah Kerr, Cary Grant

A classic and the OG “let’s meet at the Empire State Building” romance (eat your heart out, Sleepless in Seattle). Nickie and Terry meet on a transatlantic ocean liner and, though both are involved with other people, are attracted to each other. As their trip reaches its end they agree to meet one another at the Empire State Building in six months. But Nickie is alone at the appointed time and is left to wonder why Terry rejected him.


Promotion still from Sunday in New York starring Jane Fonda and Rod Taylor.via Collectors

Sunday in New York (1963)

Starring: Jane Fonda, Rod Taylor

To watch a 1960s sex comedy is to view the struggles of an entire culture as it wrestles with a topic which hitherto had been entirely taboo. Eileen fears she’s the only 22-year-old virgin left in the world and, on the heels of a bad break-up, has come to New York City to visit her brother only to find that he is out of town. She takes the opportunity to find a willing partner on a rainy Sunday afternoon.


Promotion Still from The Glass Bottom Boat starring Doris Day and Rod Taylor

via Collectors

The Glass Bottom Boat (1966)

Starring: Doris Day, Rod Taylor

Rod Taylor for two because, let’s face it, he’s a hot Robin Williams. Jenny is a widow, student, and a docent at NASA aerospace research labs and, in her spare time, acts as a mermaid for her father’s glass bottom boat tours. On one of her underwater excursions, her mermaid’s “tail” is caught on a fishing line and necessitates a meeting with the fisherman, Bruce. Jenny will soon learn that Bruce is also a top scientist and one of her bosses at NASA.


Disclaimers are to be made any time these culturally dated films are involved. Time period does not a sufficient excuse make for the exclusions and erasures made in classic film. But, with an awareness of their failures, they may be enjoyed for the merits they do contain. This list in particular consists entirely of heteronormative relationships. We are always welcome to suggestions and would be most pleased to learn of any films you consider to be worthwhile, out of the norm, or ahead of their time!


Let us know your opinion of these films in the comments below! And, if you’d like to take part in some classic film watch-alongs, be sure to join our Patreon, where you can support us with as little as $1 per month. One of these films will make a showing at our Birthday Party in March! Can you guess which one?


Featured image