Top 10 Times Romance Movies Took a Risk

This Frank Capra film might not have been the first rom-com, but it did perfect a road map that Hollywood is still following almost 90 years later. Given the film’s impact, it’s no wonder why “It Happened One Night” swept the Oscars. The production wasn’t without considerable risk, though, this genre being largely untested in 1934. Few could’ve realized they were making a classic, especially leading lady Claudette Colbert, who thought it would be “the worst picture in the world” upon wrapping. Through a heartfelt script, sharp direction, and genuine chemistry between the leads, the crew turned in something that was not only charming, but expectedly revolutionary. Capra attributed the film's success to “being in the right place at the right time.”

Even with the rise of New Queer Cinema in the 90s, LGBTQIA+ relationships were rarely explored beyond independent films. Whenever the subject arose in mainstream pictures, it was usually played for laughs. “Brokeback Mountain” marked a turning point with a previously Oscar-nominated director, an all-star cast, and a tragic love story that this crew was committed to doing justice. In addition to igniting controversy among the far-right, the film was a financial gamble with no guarantees that people outside of the LGBTQIA+ community would show up. Despite being challenged in parts of the world and inexplicably not winning Best Picture, “Brokeback Mountain” grossed more than ten times its budget, showing that queer cinema is universal. The same can be said about love.

When Charlie Kaufman is involved, risks are going to be taken. Given Kaufman’s track record as a storyteller, they might not be huge risks per se. Even so, “Eternal Sunshine of the Spotless Mind” took a big swing with a complicated plot about erasing memories. At the film’s core was a relatable romance that kept the story grounded, even as the walls of sanity close in on Jim Carrey’s Joel while he attempts to preserve the memory of Kate Winslet’s Clementine. The film is full of unforgettable imagery, but for anyone who’s ever experienced love and heartbreak, it’s the emotions you’ll remember above all else. The scenario may be fantastical, yet “Eternal Sunshine of the Spotless Mind” feels more honest than most traditional romances.

Richard Linklater has a gift for making seemingly simple movies that are more ambitious than anticipated. “Before Sunrise” was experiential for 1995, being light on plot, yet overflowing with personality thanks to the natural chemistry between Ethan Hawke and Julie Delpy. It was a novel approach to storytelling. What proved even more unique was revisiting Jesse and Céline’s relationship after nine years… and again another nine years later. Whether they end happily or tragically, most cinematic romances remain self-contained. Linklater’s one-of-a-kind trilogy demonstrates how life goes on and, more significantly, how people mature with the passage of time. Throughout this 18-year journey, we come to know Jesse and Céline intimately, as if they’re real people we want to catch up with every decade or so.

At a time when African-American-led films were primarily restricted to blaxploitation, “Claudine” went in a more authentic direction, painting a portrait of life and love. Diahann Carroll plays the titular Claudine, a single mother struggling to provide for her six children. Upon meeting a garbage collector named Rupert, played by James Earl Jones, Claudine finds happiness, yet faces several new challenges. The film explores welfare, failed marriages, child support, unemployment, and a system designed to make certain people fail no matter what they do. “Claudine” doesn’t wrap itself up in the tidiest of packages, but it reminds audiences that if loved ones stick together and support each other through the harsh realities of life, hope will always be waiting around the corner.

During a decade where few comedies ventured beyond PG-13 boundaries, “There’s Something About Mary” fully committed to achieving an R rating. This wasn’t the only risk that the Farrelly brothers took. Gross-out comedies were known for making people laugh, gasp, and cringe, which this film more than succeeded in doing. What caught viewers off guard was the movie’s heart. In a story full of politically incorrect humor and bodily fluids, the audience shouldn’t get invested in the romance. For all of its messed up moments, though, the central love story managed to be sincere. It was a different kind of date movie that mutually appealed to seemingly opposite demographics. It goes to show that you can’t spell immaturity without maturity.

There are age differences, and then there’s Harold and Maude. The age gap of nearly 60 years isn’t even the most uncomfortable aspect of this dark comedy, which might be why the reception was initially mixed. “Harold and Maude” is now considered a quintessential 70s movie with more people realizing why it works. As different as the titular outcasts are, it’s hard to deny that they’re anything less than soulmates. Some might say that they were born too far apart, although it’s serendipitous that the two met when they did. Harold may still be obsessed with death by the end, but having known the free-spirited Maude, his life will never be the same. Whether you’re 19 or 79, love can be eternally rebellious.

Speaking of rebellion, “The Graduate” is a definitive counterculture movie with another age gap at the center. In the most complicated of love triangles, Benjamin finds himself between the much older Mrs. Robinson and her daughter Elaine. The story goes to risque places, coinciding with the end of Hollywood’s golden age and the beginning of New Hollywood. The biggest risk comes in the final scene, which flips the supposed happy ending on its head as two characters share a look of uncertainty with reality sinking in. This unconventional ending signified that audiences were ready for more layered storytelling where the message isn’t spelled out, true love doesn’t solve everything, and what seems like a grand gesture can actually be the biggest mistake of one’s life.

We’re all familiar with the formula of boy meets girl, boy loses girl, boy finds girl again. “Annie Hall” adds several other steps with the central relationship ultimately leaving us on a bittersweet note. This isn’t the only way that the film plays with the usual conventions of romantic comedies. Telling parts of the story out of order, experimenting with different mediums like animation, and regularly breaking the fourth wall, there wasn’t another romcom quite like “Annie Hall” upon release. It prompted a rethinking of the genre while still encompassing all of the essential elements. Outside of relationships, the film is about nostalgia and the people who simultaneously represent a simpler time and the most confusing time of a person’s life.

Two relationships are at the heart of “Guess Who’s Coming to Dinner.” One is between John and Joey, an interracial couple. The other is between Joey’s parents, Matt and Christina. The film is just as much about the latter two, who have reservations about their daughter’s fiancé. Aside from the age difference and the fact they haven’t known each other long, skin color is the main concern. While Matt and Christina consider themselves open-minded, they fear the struggles this union will inevitably bring. During the film’s production, interracial marriage was still on the verge of being legalized in every U.S. state. This made for a landmark film with the inclusion of comedy and romance emphasizing that race relations were moving in the right direction.

Which romance movie do you think took the biggest risk? Let us know in the comments.