Best Romantic Comedies of All Time

Have you ever felt you’re living the same day over and over again? That’s what happens to cynical newsman Phil (Murray), who goes to Punxsutawney, Pennsylvania to cover the annual ritual of a groundhog emerging from his hole to predict whether there will be an early spring, or endless winter. After realizing he’s stuck re-living the same day, Phil decides to become a better person and explore love with his producer, Rita (MacDowell).

When con artist Jean Harrington (Stanwyick) picks what she thinks is the perfect mark — rich, naive Charles Pike (Fonda) — she finds herself the mark instead when she falls for him. Pike dumps her when he learns of her deception. But she devises another persona — the Lady Eve Sidwich — to win him back. Somehow it works and the two admit they really do love each other once she drops her fake identity and he forgives her.

A battle between communism and capitalism plays out in a romantic comedy about a stern Russian functionary, Nina Ivanovna “Ninotchka” Yakushova (Garbo), sent to Paris to keep some fellow Russians in line as they sell confiscated jewels for the good of the motherland. Instead of doing her job, she finds herself falling in love with charming Count Léon d’Algout (Douglas). How do we know it’s love? He makes her laugh — quite a turnabout for the usually stoic Garbo.

After Regina Lampert (Hepburn) learns that the husband she had planned to divorce has been murdered, she finds herself the target of thieves who want the money they believe her late spouse stole during World War 11. The rather convoluted plot is hard to follow at times, but not so the budding romance between Hepburn and Cary Grant, who may or may not be a good guy.

In this pre-#MeToo era picture, divorced middle-aged writer (Allen) falls for and then breaks up with 17-year-old Tracy (Hemingway), arguing that she is too young for him. (She is.) He then enters into a relationship with the mistress (Keaton) of a cheating friend, only to realize he shouldn’t have let Tracy go. Perhaps the true love story in this film isn’t between a man and women, but between Allen and the island of Manhattan, which is romantically depicted in beautiful black-and-white images accompanied by George Gershwin’s bittersweet songs.

Auntie Mame Dennis (Russell) raises her young nephew, Patrick, after the boy’s father dies. When the 1929 stock market crash bankrupts Mame, she and Patrick go on a series of adventures as the free-spirited aunt tries to get Patrick to loosen up and live life to the fullest, despite the protests of the straitlaced trustee of his fortune. Mame loves and loses one husband, but never loses her zest for life.

Snobbish butler Marmaduke Ruggles finds himself in the remote Washington state town of Red Gap in 1908 after his employer, a British earl, loses his services in a card game to millionaires Egbert and Effie Floud. At first, Ruggles doesn’t fit in with the rough American crowd, but soon finds himself falling in love with his adopted homeland, where he can be what he wants to be.

Two rich, pampered socialites (Keaton and McGuire) find themselves stranded on a cruise ship. Although McGuire had previously rejected Keaton’s proposal, the two learn how to survive together — and fall in love — during a series of comedic missteps in this silent classic.

Sibling rivalry factors into the plot of this rom-com as Johnny (Grant) plans to marry rich Julia (Nolan), but falls instead for her sister, Linda (Hepburn). Johnny wavers between wanting to please his future in-laws by getting a job, or taking a holiday. In the end, he chooses freedom and Linda.

Proper grammar professor Bertram Potts (Cooper) meets nightclub performer Katherine “Sugarpuss” O’Shea to study American slang. The two are attracted to each other, and she hides in his home to escape questioning by the police, who are after her mob boss boyfriend. After Bertram busts up a wedding between Sugarpuss and the mobster, Sugarpuss says she isn’t good enough for the professor. His kisses convince her of his love.

Newspaper editor Walter Burns (Grant) desperately tries to stop the marriage of his ex-wife, star reporter Hildy Johnson (Russell), by asking her to file one last story on a wrongly convicted murderer. In the end, the man is saved and Hildy and Walter end up together again.

Down-on-his luck Godfrey “Smith” Parke (Powell) becomes the butler for the rich family of Irene Bullock (Lombard) in one of the first so-called screwball comedies. Parke, who is actually from an elite Boston family, ends up saving the Bullock’s fortune and gets back on his feet. And Irene gets her man Godfrey.

Remembered today more for the sublime dancing of its two stars than for its story line, “Top Hat” follows Dale Tremont (Rogers) and Jerry Travers (Astaire) as they fall in love. But she’s reluctant to pursue him because she mistakenly thinks he is the cheating husband of a friend. He’s not, and eventually he wins her over with one final dance.

Can a romantic comedy be a romantic comedy when the couple breaks up at the end? Yes, if it’s comedian Alvy Singer (Allen) and singer Annie Hall (Keaton), who like many couples love each other, but grow apart. Told from Singer’s point of view, the movie examines why the relationship went wrong. Even though he’s sad at the end, Singer admits that he was glad he fell in love with Annie and that love is worthwhile even when it doesn’t end well..

Junior broker Jimmy Shannon (Keaton) is elated to learn he will inherit $7 million — but only if he marries that same day. He asks his sweetheart Mary Jones (Dwyer) to marry him, but when she finds out it’s because of the money, she refuses. Jimmy then frantically asks other women to be his bride, even putting an ad in the newspaper. In the end, Jimmy convinces Mary to marry him just in time to inherit the money.

Crown Princess Ann (Hepburn) escapes from her stifling royal duties with American newspaper reporter Joe Bradley (Peck) for a whirlwind day in Rome. Joe knows who she is, but doesn’t report on their day together. The movie ends with Ann returning to her royal life, and Joe content with his memories.

As a way to climb the corporate ladder at his insurance company, C.C. “Bud” Baxter (Lemmon) lets his superiors bunk in his apartment for extramarital trysts. When his boss’s mistress, elevator operator Fran Kubelik (MacLaine), attempts suicide in the apartment after finding out that the cheating boss was cheating on her, Bud saves her. Fed up with his boss, Bud quits his job, but finds himself a girl — Fran.

In this melancholy silent movie, the Tramp (Chaplin) stumbles into a circus and finds love with a mistreated horse rider (Kennedy). Unfortunately, she loves someone else, a tightrope walker, Rex. In a rarity for a rom-com, the Tramp doesn’t end up with the girl. Instead, he smiles as the tightrope walker and the horseback rider move on together and he leaves the circus.

A comedy of mistaken identity, two musicians Joe and Jerry (Curtis and Lemmon) escape the mob after witnessing the infamous St. Valentine’s Day Massacre in Chicago. Dressing up as women to join an all-female band traveling the country, Joe (Curtis) falls for Sugar (Monroe) and Jerry finds himself the love object of another man. Sugar and Joe kiss in the end, and Jerry admits to his admirer that he is, in fact, a man. Unfazed, his suitor says, “Well, no one’s perfect.”

Snobbish Tracy Lord (Hepburn) is set to marry George Kittredge, but is soon distracted by reporter Macaulay “Mike” Connor (Stewart) — and her ex-husband, C.K. Dexter Haven (Grant). With too attractive men to choose from, can Tracy go wrong?

Warring shop clerks Alfred Kralik (Stewart) and Klara Novak (Sullavan) are really secret pen pals. The two fall in love through their written words, but don’t know they are really co-workers, setting off a series of miscues. Once that little misunderstanding is cleared up, the two finally declare their love for each other.

Heiress Ellen “Ellie” Andrews (Colbert) hightails it away from her father, who wants to annul her marriage to a fortune hunter. She meets up with unemployed newspaper reporter Peter Warne (Gable) on a bus trip to New York City. When the bus breaks down, Ellie and Peter hitchhike and (you guessed it) fall in love.

A movie projectionist (Keaton) falls in love with a beautiful girl, but his rival for her affections, “the sheik,” frames him for stealing a watch from the girl’s father. The projectionist falls asleep and dreams that he is Sherlock Holmes, tracking down the thief. The happy ending finds the awakened projectionist and his love together and the rival exposed.

Famed for its singing and dancing and Technicolor photography, “Singin’ in the Rain” is about a silent movie star, Don Lockwood (Gene Kelly), who falls in love with a chorus girl, Kathy Selden (Reynolds), just as “talkies” are threatening to overtake silent films. But Kathy proves elusive and Lina (Hagen), Don’s frequent leading lady, thinks Don is in love with her. Lina’s secret is that she sounds squeaky and unpleasant, and Kathy dubs her voice on film. All is eventually, and Kathy and Don kiss at the film’s end.

The Little Tramp (Chaplin) falls for a blind flower girl (Cherrill). This classic silent movie displays Chaplin’s immense gift for physical comedy, but its heart comes from the flower girl accepting him as he is after he pays for the operation to restore her sight. What could be more romantic than that?