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Classic Movies for a Romantic Valentine’s Day

4 minute read

By Katie Ormsby

Valentine’s Day is perfect for enjoying romantic classics. Romance, however, isn’t limited to sweeping love stories. It can be found in thrillers and musicals, too. With this in mind, we’ve curated a selection of classic movies that capture love — sometimes in unexpected films. These films span genres, from more traditional romances and romantic comedies to suspense films and musicals. Start a search today to find classic movies for a romantic Valentine’s Day.

Shutterstock: SeventyFour

Casablanca (1942)

“Casablanca,” starring Humphrey Bogart and Ingrid Bergman, is a quintessential romantic film. Set against the backdrop of World War II, it tells a tale of love, sacrifice, and moral dilemma. Bogart plays Rick Blaine, a cynical nightclub owner. When his former lover Ilsa (Bergman) arrives, their reignited passion becomes a poignant story of unfulfilled love.1

The Philadelphia Story (1940)

“The Philadelphia Story” is a romantic comedy that sparkles with wit and charm. Katharine Hepburn stars as a strong-willed heiress navigating pre-marital jitters. Cary Grant and James Stewart play her former husband and an intrusive reporter, respectively. The film’s clever dialogue has made it an enduring favorite.2 The charming musical remake “High Society” (1956), starring Grace Kelly and Bing Crosby, is also worth a watch.3

Charade (1963)

“Charade” combines romance, suspense, and comedy in a stylish Parisian setting. Audrey Hepburn and Cary Grant’s chemistry is palpable, providing a blend of romance and adventure. Hepburn’s portrayal of a widow caught in a web of mystery is both elegant and spirited. Grant, as the charming yet mysterious stranger, adds layers of intrigue.4

Singin’ in the Rain (1952)

“Singin’ in the Rain” is a joyous celebration of love and cinema starring Gene Kelly, Debbie Reynolds, and Donald O’Connor. Its portrayal of Hollywood’s transition from silent films to talkies is humorous and heartwarming with dazzling song-and-dance numbers and a sweet love story at its core.5 For more Gene Kelly, watch “An American in Paris” (1951) — another dreamy and romantic picture.6

Pillow Talk (1959)

“Pillow Talk” is a rom-com that showcases the undeniable chemistry between Doris Day and Rock Hudson. The film offers a playful and witty take on romance and relationships. The comedic timing of Day and Hudson and the film’s clever script provide plenty of laughs. This movie is a lighthearted — and somewhat risqué — choice for a romantic movie night.7

Rear Window (1954)

Alfred Hitchcock’s “Rear Window” is a thrilling blend of romance and suspense. James Stewart stars as an injured photographer confined to his apartment, with Grace Kelly as his glamorous and resourceful girlfriend. Their relationship unfolds against a backdrop of mystery and intrigue. The film’s suspenseful plot, romantic tension, and great comedic moments from Thelma Ritter make it a must-watch.8

The Umbrellas of Cherbourg (1964)

“The Umbrellas of Cherbourg,” starring Catherine Deneuve, is a visually stunning and emotionally charged musical. The film stands out for its continuous use of song, replacing spoken dialogue entirely. The story of young love and heartache is enchanting and poignant.9 Follow it up with “The Young Girls of Rochefort” (1967), another dreamy — though cheerier — Jacques Demy musical with Deneuve.10

My Favorite Wife (1940)

“My Favorite Wife” is a humorous and romantic screwball comedy starring Cary Grant and Irene Dunne. It cleverly deals with second chances in love. You see, Grant’s wife (Dunne) makes a surprising return after being presumed dead — on the day he gets remarried.11 The film’s approach to romance makes it a delightful classic. “The Awful Truth” (1937), another Grant and Dunne screwball comedy, is also fun.12

Roman Holiday (1953)

“Roman Holiday” is a fairy-tale romance set in the picturesque city of Rome. Audrey Hepburn, in her breakout role as a princess exploring Rome incognito, is both graceful and endearing. Gregory Peck, the American journalist who falls for her, provides a perfect counterpart. It’s a delightful escapade that captures a whirlwind romance.13

The Red Shoes (1948)

“The Red Shoes” is a visually stunning film that explores the intersection of love and art. Moira Shearer stars as a talented ballet dancer torn between her passion for dance and her love for a composer. The film’s breathtaking dance sequences and its exploration of the sacrifices made for art make it a captivating watch. “The Red Shoes” isn’t just a film about ballet — it’s a timeless story of love, ambition, and the choices we make.14

Get Carried Away With Romantic Classics

From the witty banter of “The Philadelphia Story” to the Technicolor visuals of “The Red Shoes,” these films are perfect for setting a romantic mood on Valentine’s Day. Even thrillers like “Rear Window” intertwine suspense with romantic elements, proving love stories can thrive in any genre. So, cozy up with your loved one, grab some popcorn, and let these classic romances rekindle the magic of love on this special day.

Katie Ormsby



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