The romance movie: whether sitting down to watch it with a special someone on Valentine’s Day or binge-watching romantic comedies during an existentialist crisis, it is here to stay permanently. The early days of the genre featured the likes of Greta Garbo and John Gilbert, one of Hollywood’s earliest golden pairings, but now it seems as if every movie has a dash of romance added into it, even for Spider-Man and Thor. It takes dedication to focus on the romantic elements, and, during the World War II-era of Western cinema, romance was thriving.
Film history tends to transition back and forth between classic romantic movies to romantic comedies, but there’s one aspect of these kinds of movies that remain consistent: the screening location. Movie theaters have always been a place for lovers to escape to the back row for a few hours, while drive-in movies offer the quiet privacy of being within your car. Today’s world might be obsessed with Zendaya and Tom Holland’s relationship, but nothing beats the classic Hollywood romances deeply embedded into American cultural history. These are the most romantic classics in Hollywood’s history.
9 West Side Story
The 2021 and 1961 versions of West Side Story were originally based on the theatrical musical that hit Broadway stages back in 1957. While Broadway was not accessible to the average person, the 1961 film adaptation of West Side Story brought the story of Maria and Tony to larger audiences across the world. The original film adaptation does have some big representation problems, but its romance has inspired the generation that grew up with the movie. West Side Story was also one of the first movies to depict interracial marriage, which was largely illegal in the United States until 1967.
8 Roman Holiday
Roman Holiday was legendary actress Audrey Hepburn’s first major film role, and she was unforgettable as Ann, a princess exasperated with her royal life. The movie features one of the most romantic cities to be a whimsical, free soul looking for an outlet: Rome. And it’s an American reporter, played by Gregory Peck, who finds the passed-out princess on a park bench, sparking a series of events that’s both charming and lighthearted. Roman Holiday is a romantic comedy that almost feels like a love letter to Rome.
7 Some Like It Hot
Marilyn Monroe is one of the most-recognized actors from the 1950s, leaving behind a prolific legacy and mythology about who she was as a person and actor. Some Like It Hot was her 1959 hit set during Prohibition-era Chicago. Her love interest is Joey Curtis, a saxophone player pretending to be a woman. He befriends Monroe’s character under two different identities, making this situation a lot trickier. Some Like It Hot is one of the greatest films ever made, and it deserves that reputation for a myriad of reasons that one would have to watch it to truly understand.
6 An Affair to Remember
An Affair to Remember was ranked one of the most romantic films by the American Film Institute among many other classic movies. Nickie Ferrante (Cary Grant) is a playboy going back to New York from Europe when he meets his match in Terry McKay (Deborah Kerr). Neither of them is in a relationship that they are happy in, and they want to seek out new opportunities in the world. While the two are briefly separated and tragedy strikes, the story shifts and becomes a testament to the power of fate and destiny.
5 Sabrina
Sabrina marks a unique relationship in the film world: Audrey Hepburn and Givenchy collaborated for the first time, creating a staple in the movie world and a wardrobe for the starlet that became iconic. Hepburn stars as Sabrina, a young woman madly in love with David Larrabee (William Holden). He previously has not given her any attention, but everything quickly changes after she meets his brother Linus (Humphrey Bogart). Sabrina is romantic and sweet, yet another lighthearted Hepburn movie that captivates audiences globally.
4 Singin' in the Rain
Singin’ in the Rain was not a big hit when it was released, but, like fine wine, it got better with age. The movie is considered one of the finest Hollywood movies to have ever been made, which is why it was selected in the first batch preserved in the National Film Registry. Gene Kelly is Don, a silent film star whose popularity is threatened with new talkies taking over the movie world. He’s in love with Kathy (Debbie Reynolds), a chorus girl that appears in movies. Colorful and daring, Singin’ in the Rain makes a grand impression.
3 City Lights
It must be difficult to express and portray romance without words, but Charlie Chaplin can do it all. City Lights is a silent film, but it still creates a romantic comedy within its storyline. Chaplin’s Tramp falls in love with a blind woman (Virginia Cherrill) that sells flowers. After befriending a drunk millionaire after preventing his suicide, The Tramp begins his grand plan of wooing his love interest. City Lights is tender and hilarious, creating the perfect romantic comedy despite being a silent film released when silent movies were dying.
2 Gone With the Wind
Gone With the Wind has a lot of problems—many representations of the era and topic that it comes from—but despite its problems, it is capable of being a powerful romance. Scarlett O’Hara is brought to life by actress Vivien Leigh, and she wants to romantically pursue a married man, Ashley Wilkes (Leslie Howard). The daughter of a plantation owner in Georgia, she and the other characters struggle with the impacts of the Civil War and the eventual loss of the Confederacy. Gone With the Wind is a grand epic reminding what the South lost and is about to enter.
1 Casablanca
Morocco is the setting of Casablanca, and expat Rick Blaine (Humphrey Bogart) refuses to align himself in any conflict. He owns a nightclub in Casablanca, and his former love (Ingrid Bergman) has just made a reappearance. Her husband is a Czech resistance leader, forcing Blaine to decide between his love for her and helping her husband. Casablanca is seductive, a melodrama that amps up the romance and has sustained immense popularity for almost a century after its initial release.