Top 10 Romance Movies That Should Have Won An Oscar
#10: “Punch-Drunk Love” (2002)
Adam Sandler is known for his work in comedies, but his more well-rounded performance in this romantic comedy-drama was widely praised by critics. It garnered him a Golden Globe nom ― but recognition in the Oscars’ Best Actor category wouldn’t have been a long shot either. Sandler stars as Barry Egan, a single man who finds himself suffering from social isolation. His strained relationships with seven strong-willed siblings don’t help. He does find some relief, however, in a relationship with his sister’s colleague, Lena. Shielding the budding romance from different kinds of outside interference proves difficult, but it’s downright heartwarming to watch.
#9: “Rushmore” (1998)
Wes Anderson’s second feature film helped establish his one-of-a-kind visual and narrative style. Besides bringing him to prominence, it also bolstered the careers of first-time actor Jason Schwartzman and industry vet Bill Murray. It’s even been preserved in the U.S. National Film Registry. Co-written by Owen Wilson, the movie is a semi-autobiographical depiction of an idiosyncratic teen at an elite prep school. While he strikes up a friendship with a much older parent, they end up bitter rivals over their mutual feelings for a teacher. Combining quirky humor with the bittersweet intensity of adolescence, it’s the perfect high school movie for grown-ups. While “Rushmore” picked up a couple of Independent Spirit Awards, it’d be a few years until Anderson got his first Oscar nomination.
#8: “500 Days of Summer” (2009)
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This romantic comedy-drama takes a truly inventive approach to an age-old story. The acclaimed sleeper hit garnered Golden Globe noms, but unfortunately no recognition from the Academy. It tells the story of Tom, a man working an uninspiring job as a greeting card writer who becomes enamored with a colleague. Their changing dynamic is depicted through a nonlinear narrative, with the film cycling through numbered days in their relationship. Beyond this narrative device, the film also boasts interesting features like a song-and-dance break and an “expectations vs. reality” split-screen shot. But perhaps most importantly, it’s also a compelling and heartbreaking love story.
#7: “Crazy Rich Asians” (2018)
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Despite receiving nominations for Golden Globes, Critics’ Choice Awards, and Screen Actors Guild Awards, this blockbuster went totally unacknowledged by the Oscars. There’s no question that a film’s high-profile status can influence its appearance on the Oscar ballot. And as the 2010s’ highest-grossing rom-com, it’s puzzling why the film didn’t receive a single nomination. Adapted from the 2013 novel of the same name, it stars Constance Wu as a Chinese-American economics professor who visits her boyfriend’s family in Singapore. As it turns out, they’re ridiculously wealthy, and his mother is particularly disapproving. With stellar performances and a central relationship that you can’t help but root for, this movie was undoubtedly snubbed.
#6: “Weekend” (2011)
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Sure, this British film had a more low-profile release than some Academy Award-winning titles. But if its critical reception is any indication, it was certainly worthy of an Oscar nom. The tender romantic drama follows a fateful weekend for two strangers with incredible chemistry. In the course of their brief but intense affair, protagonist Russell comes to terms with his upbringing and internalized shame. At the same time, he and his lover Glen work through the latter’s commitment-phobia. Although the bond the two characters form is touching, the movie is a bittersweet viewing experience. With Glen’s departure to the U.S. planned for Sunday, we can sense that the chemistry-filled relationship can’t last forever.
#5: “Before Sunrise” (1995)
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Despite boasting a 100% Rotten Tomatoes score, Richard Linklater’s first “Before” trilogy film didn’t receive a single Oscar nom. It follows two strangers who meet on a train crossing Europe and decide to spend a night together in Vienna. The film is replete with thoughtful dialogue as Jesse and Céline make all kinds of conversation. And with chemistry that is simply off the charts, it’s no wonder why the movie’s central duo can keep up the talking. The performances are impressively naturalistic, and viewers may even feel like they’re watching a real couple fall in love. Although Linklater would receive Academy Award nominations down the line, the lack of attention for “Before Sunrise” is surprising.
#4: “In the Mood for Love” (2000)
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Hong Kong filmmaker Wong Kar-wai’s catalogue has only garnered two Academy Award nominations. Even then, these weren’t in “Big Five” categories and the auteur himself has never received a nod. Although we can’t change history, there would have been no better contender for major award success than this romantic drama. It’s considered by some major outlets to be one of the greatest films of the 21st century, and for good reason. The film follows two lonely stay-at-home spouses living in the same apartment complex. As they begin to enter more meaningfully into each other’s lives, they also become aware that their partners are having an affair. Their ill-fated attempts to make a relationship work span several years, making for an understated yet epic tale.
#3: “Bringing Up Baby” (1938)
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This zany picture didn’t initially perform well at the box office, which perhaps partly explains its lack of Academy Award noms. Hindsight is 20/20, however, and a screwball comedy starring Cary Grant and Katharine Hepburn at the height of their powers seems mighty Oscar-worthy now. The Hollywood hunk plays a paleontologist whose encounter with a free spirit throws the day before his wedding into total disarray. To his surprise, it turns out to be an utter joy, if a bit stressful. The film is downright hilarious, and the chemistry between Grant and Hepburn is palpable. It enjoys iconic status now, but there’s no question it deserved better recognition back in the day.
#2: “Portrait of a Lady on Fire” (2019)
This film was in the top three contenders for the French submission to the Best International Feature Film category. Although it sadly wasn’t chosen, it was decorated with many other awards and a whopping 98% Rotten Tomatoes score. However, we still think it was deserving of arguably the highest film industry honor worldwide. The beautiful and devastating film follows a painter in the late 18th century who falls in love with her artistic subject. Although the pair strike up an affair while producing a portrait, the sitter’s engagement forecloses their future. With striking visuals and wistful romance in spades, it’s a heavy-hitting drama in every way.
#1: “Singin’ in the Rain” (1952)
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This iconic musical rom-com covers a transitional period in the motion picture industry. In the late 1920s, the silent films that had reigned supreme are in their final days as “talkies” gain prominence. Hollywood star Don Lockwood meets Kathy, a pretentious stage actress who turns out to be a mere chorus girl. He falls for her regardless and conspires to replace his irritating co-star Lina’s voice with hers. Although it’s considered one of the best films of all time, it received only two Oscar noms and none in a “Big Five” category. If you ask us, any one of its iconic song-and-dance sequences make it more than deserving.
