5 Underrated Rom-Coms to Watch This Month

As an aficionado of romantic comedies—from the era of black-and-white screwballs to today’s AI-generated Netflix originals and everything in between—I live for the chance to get on my soapbox and talk about this sometimes denigrated, often beloved genre. We may have lost the recipe for solid rom-coms somewhere in the late 2000s, but luckily there’s a never-ending backlog of older romances to choose from. While you wait for the rest of this month’s lovesuite screenings at Hyperreal Film Club, check out these five underlooked gems. 

1. Imagine Me & You (2005)

This is your standard mid-2000s rom-com, complete with a last-ditch attempt to win the girl’s heart as she’s en route to the airport, with one important twist: they’re lesbians! When Rachel (Piper Perabo) locks eyes with Luce (Lena Headey) at a wedding, sparks immediately fly. The only problem is it’s Rachel’s wedding to a man and Luce is their florist. Whoops!

What follows is a surprisingly forward-thinking plot, as Rachel wrestles with new realizations about her sexuality and Luce maneuvers the classic lesbian trope of falling for a so-closeted-she-thinks-she’s-straight girl. Imagine Me & You avoids getting bogged down in melodrama, instead letting its audience get swept up in Rachel and Luce’s sweet romance with the eventual support of their friends, family, and Rachel’s husband. It’s a Y2K cheesefest without a deeper message than “true love prevails,” but don’t gay girls deserve that?

2. Brown Sugar (2002)

Full disclosure: I discovered this movie while on a Sanaa Lathan thirst-watch binge (Blade, Love & Basketball, etc.). Brown Sugar follows the typical beats of a 2000s romantic comedy, but there’s something special at the heart of this one. 

Our love interests Sidney (Lathan) and Dre (Taye Diggs) are childhood best friends from New York City, and they share a deep love of hip-hop that informs their careers and their relationship over time. In the very first scene of the movie, we’re treated to a bevy of cameos from Talib Kweli, Method Man, Slick Rick, Kool G Rap and more sharing how ‘80s hip-hop shaped them. This affection for a specific time and place carries through the rest of the movie, as we watch Sidney and Dre navigate career ups-and-downs, romantic pitfalls, and the evolution of their friendship into something they both try to deny. Nicole Ari Parker, Queen Latifah, Mos Def and the beautiful Boris Kodjoe fill out the rest of the cast in similarly nuanced and fun characters, with Mos Def at one point delivering a riff on Casablanca that lives rent-free in my head to this day.

3. Crossing Delancey (1988)

Joan Micklin Silver is a criminally under-heralded director. Her 1977 dramedy Between the Lines, about a community-centered alt-newspaper facing a major corporate merger, remains uncomfortably prescient. And in Crossing Delancey, Silver gives us an enduring ‘80s ethnic rom-com in the vein of Moonstruck. Studio executives actually found the movie “too ethnic” (i.e., too Jewish), but thanks to help from Steven Spielberg, then the husband of Crossing Delancey’s star Amy Irving, the movie ended up with a Warners Bros. distribution.

Based on a play by the same name, Delancey places its audience in the day-to-day life of New York bookseller Isabelle Grossman (Irving). Isabelle is happy with her career and her social circle, and less happy with her bubbe’s attempts to matchmake Isabelle with every eligible Jewish bachelor in Manhattan—including Sam (Peter Riegert), a pickle shop owner on the Lower East Side. The script, filled with writerly conversations a la Whit Stillman, takes us along Isabelle’s journey from prioritizing the pretentious literati around her to overcoming her initial disdain of Sam’s blue-collar background. Much like Moonstruck, we get a loving portrait of a distinct family and culture, as well as a romance delivering some of the swooniest lines heard on screen.

4. Splendor (1999)

I grew up watching the progenitor of modern rom-coms: screwball comedies from the ‘30s and ‘40s. Every trope you know and love (or hate) originated in a Cary Grant or Barbara Stanwyck-helmed flick, from forced-to-share-one-hotel-room to fake dating and everything in between. When Hyperreal screened Gregg Araki’s Splendor last month, I was delighted to find a contemporary-ish movie that understands not only the standard tropes of that genre, but also the spirit and slapstick silliness of screwball giants like Ernst Lubitsch, Preston Sturges, and Howard Hawks.

In Splendor, we follow small-town girl turned struggling L.A. actor Veronica (Kathleen Robertson) as she meets and falls for two polar opposites: the cerebral Abel (Johnathon Schaech) and the himbo Zed (Matt Keeslar). Veronica starts dating both men separately, and then together. As she forms a makeshift polycule, Abel and Zed evolve from competitors to roommates and, eventually, friends, bonded by their shared love of Veronica. Araki drew inspiration for the movie from Lubitsch’s pre-code Design for Living, and Splendor mirrors its predecessor by turning heterosexual marriage conventions on their head with an unorthodox idea of what love can look like. Splendor even takes cues from screwballs with its stock side characters, like Veronica’s long-suffering, pragmatic best friend Mike (Kelly Macdonald) and stuffed-up suitor Ernest (Eric Mabius), the Ralph Bellamy to Zed and Abel’s Cary Grant. Like all great rom-coms, Splendor requires a light suspension of disbelief, and like every screwball comedy, each plot thread and problem is neatly tied up in the last 3 minutes. 

5. Libeled Lady (1936)

If you need an introduction to screwball, Libeled Lady is a perfect entrypoint, anchored by snappy dialogue and three of Old Hollywood’s best comedic actors (Spencer Tracy is there, too). This 1936 movie presents themes already well-established in the genre: enemies-to-lovers, class differences, marriages of convenience, etc. We’re immediately launched into the whole mess as the newspaper Warren (Tracy) works at prints an article incorrectly reporting that spoiled heiress Connie (Myrna Loy) had an affair with a married man. Connie slaps the newspaper with a multi-million-dollar libel suit, and Warren must rely on his fed-up fiancée Gladys (the effervescent Jean Harlow) and former colleague/current frenemy Bill (William Powell at his most suave) to entrap Connie in an actual affair. 

Obviously Gladys and Bill have to get married, and Gladys falls for Bill, and Bill falls for Connie as he’s attempting to ensnare her in a lie to get the paper and Warren out of trouble. The convoluted plot is pulled off by Loy, Powell, and Harlow playing off each other and sticking the landing on every joke, no matter how silly. Moments of zaniness are offset by swoony scenes of Bill chipping through Connie’s ice queen exterior, and in the final minute(!) of the movie we get to see everyone—except poor Gladys—end up happy, against all odds.