The art of the rom-com is a delicate thing. Among all the meet-cutes, falling-in-love montages, and temporary breakups before the main characters ultimately decide they’re destined to be together, you’ll find a tricky tightrope to walk on. Oftentimes writers and filmmakers will look to add some spark and subversion to the routine formula, but you don’t want to get too far away from the ethos of what makes the genre tick or else you may lose that sense of comfort and satisfaction someone coming to it is looking for. But it’s all too often that films rely solely on the expected beats without any new insights or distinct approach, often trying to compensate with an attractive cast and settling for being perfectly agreeable. The classics are deemed so for a reason: they either codified the tropes or utilized them so well that they became impossible to deny. But for all your When Harry Met Sallys or Bringing Up Babys, there’s a vast collection of unsung rom-coms whose praises are long overdue. With Valentine’s Day right around the corner, we decided it’s time we gave them their flowers.
Here are 9 underrated rom-coms for you, and maybe your beloved’s, viewing pleasure this February 14th. May they spark some romance in your relationship, or some joy in your cold, dead heart.
A New Leaf (1971)
Typical for its writer, director, and star Elaine May, A New Leaf is an idiosyncratic representation of its particular genre. A madcap black comedy that’s at once a snarky send-up of both rom-com expectations and a sincere embrace of the power of a love story, the success of May’s film is buoyed by its endeavor to defy archetypal predictability. Co-starring alongside May is Walter Matthau as Henry, a stunted and petulant New York bachelor whose coasting off his family’s inheritance comes to a sudden halt when he finally spends himself flat broke. Terrified of destitution and having to live as one of “the poors,” he concocts a psychopathic plan to find a woman of means, marry her, and kill her to inherit her fortune. Enter May’s Henrietta, a wealthy and ambitious—though ditzy and clumsy—botanist whose awkward demeanor and shy temperament have left her perpetually single, and the perfect target for Henry’s scheme.
Essentially a screwball comedy updated for a society that was just prepared enough for its spiky brand of nihilism by the time it was released in ‘71, A New Leaf is perfectly hilarious in its cutting satire and cheeky wit. May’s blundering, irreverent performance is the perfect foil to Matthau’s brazen avarice and dry incredulity at how his plot continues to backfire on him at every turn. The committed performances and amusingly impish tone outweigh the clear signs of a compromised edit (May’s preferred, and now lost, version was three hours long), especially evident in a fitting, but abrupt, ending. But the film is undeniably wonderful in its existing form, and a distinct calling card for a filmmaker defined by striking originality.
Joe Versus the Volcano (1990)
You’d be hard-pressed to find another rom-com as brazenly bizarre and so acutely tuned into its own uber-specific frequency as Joe Versus The Volcano. While on the surface a simple Tom Hanks and Meg Ryan-led predecessor to the likes of Sleepless in Seattle and You’ve Got Mail, Joe Versus The Volcano smuggles in a distinctly weird little movie wrapped up in the veneer of early-90s commercial appeal. This is largely chalked up to its eccentric story: Hanks plays Joe, a downtrodden, perpetually sick, and depressed man with a terrible job who is all too aware of his place as a pawn within the corporate machine of capitalism. After being diagnosed with a supposed “brain cloud” and given a finite amount of time to live, he accepts an offer by a wealthy stranger to live like a king for a few weeks before voluntarily throwing himself into a volcano on the island of Waponi Woo to appease the local natives. Along the way, he meets and falls in love with one of Ryan’s three characters that she plays, Patricia.
It’s somehow both more and less preposterous than it sounds, as the film embraces its absurdity without remorse while simultaneously populating it with comedic beats and performances that speak to a more mainstream sensibility. Hanks and Ryan are as great as ever, effortlessly finding new ways to play off each other’s performances as the former perfectly embodies a man who has lost all hope attempting to gain it back, and the latter moves through the varying peculiarities of her different roles and perfectly calibrates them to her co-star. Baked into its weirdness is also an invigorating sense of optimism regarding its thematics about what makes life worth living, deepened further by the film’s jocular tone.
Love and Basketball (2000)
Admittedly, this film errs more toward drama than comedy, but any opportunity to point people toward director Gina Prince-Bythewood’s critically acclaimed yet under-discussed debut feature is one worth taking. Aptly titled, this decade-plus-spanning film charts the tumultuous relationship between Quincy (Omar Epps) and Monica (Sanaa Lathan), two childhood best friends who must contend with how their fiery passion for each other conflicts with that of their love for basketball. On top of its satisfying and well-performed love story, Love and Basketball contends with ideas of identity, gender, privilege, and the cost of ambition centered around what it means to simultaneously attempt to devote yourself to your craft as well as another person who shares your same dreams. The film mines stirring and authentic drama out of the ways Quincy and Monica fall in and out of each other’s lives over the years, and Epps and Lathan afford their characters a necessary set of layered emotional weight, as well as a warm sense of genuine love and desire.
One of the most glossed-over entries into the nostalgic period-piece coming-of-age romance canon, Adventureland succeeds because of how its adherence to formula is subverted by its drifting, melancholic mood and its emphasis on honest emotional experience. Writer/director Greg Mottola, known mostly for his work on The Daytrippers and Superbad, mines the maundering and confusing period between college and the rest of one’s life by focusing on recent college graduate James (Jesse Eisenberg), whose plans to tour Europe over the summer before going to graduate school are thwarted by sudden family money troubles. Instead, he’s forced to get a summer job at Adventureland, the dinky local theme park where he regularly has to clean up kid vomit and be verbally harassed and threatened by guests. Of course, the motley crew of employees ends up teaching him more about himself than he thought possible, particularly the presence of Em (Kristen Stewart), who sees as much as herself in James as he does in her.
Despite its indulgence in well-worn tropes and excess of conspicuous period-accurate 80s needle drops, Adventureland finds authenticity, ironically, within the unconventional matchup of its two leads. The soft-spoken, sardonic nature of both Eisenberg and Stewart makes for an irregular romantic dramedy that finds a lot of emotional truth within each of their reticent demeanors, which underlines the malaise of these characters. If that sounds too sad, let me assure you that Adventureland is very much a comedy, even if a slightly dry and downbeat one for the genre. The supporting cast includes the likes of the always-funny Bill Hader, Kristin Wiig, and Martin Starr, and even Ryan Reynolds shows up to turn in a great performance. Remember when that was a thing that would happen?
Enough Said (2013)
A staunch purveyor of the adult drama, Nicole Holofcener gently depicts the experience of what it feels like to be lost in middle age with this sweet and sharp romantic dramedy. Julia Louis-Dreyfus stars as Eva, a divorced mother preparing to send her only daughter off to college and wondering what that means for the next phase of her own life. Luckily, she strikes up two new relationships at once: a friendship with the bohemian and cool Marianne (Catherine Keener) and a burgeoning relationship with the not-quite-her-type Albert (James Gandolfini, amazing in one of his final roles before his passing), whose quiet and unconventional charm begins to win her over. But when she accidentally discovers that Albert is Marianne’s despised ex-husband whom she repeatedly laments, Eva keeps the knowledge to herself to try and glean some insight into Albert’s potential flaws.
The premise sounds like a film primed for some absurd scenarios of misunderstandings and hidden motives, but Holofcener allows it to play out with a soft, good-natured outlook that takes a genuine interest in the lives of its characters. Eva is attracted to Albert but she’s also worried about wasting her time, fearing she doesn’t have many of her good days left to afford someone that isn’t worth it in the end. But Marianne begins to color her perspective of Albert in a light that may only be confirming her biases as opposed to offering insight as to whether he would be a good match for her, making for a film that probes the question of how we perceive those we have growing feelings for and what it means to give someone a genuine chance.
What If (2013)
A true no-frills, unashamed, stick-to-the-formula romcom, What If is by turns begrudgingly charming and just genuinely endearing. Following in the footsteps of When Harry Met Sally in investigating the age-old question of if men and women can really be just friends, this will-they-won’t-they tale pairs up Zoe Kazan and Daniel Radcliffe right off the heels of the latter’s decade-long stint as the boy wizard extraordinaire Harry Potter, making it one of his initial opportunities to make an impression outside of the Wizarding World. It turns out he’s pretty dang charming as Typical Rom-Com Protagonist Guy and he, Kazan, and the supporting cast including the likes of Adam Driver, Mackenzie Davis, and Rafe Spall, all help to sell the film’s admittedly quirked-up and bantery brand of cutesy dialogue. However, where the film really shines is in its back half—this may be one of the only movies of its kind that actually gets better once it hits the requisite “the characters are mad at each other now” portion of the story, as it realistically reckons with movie tropes that are typically romanticized, like the consequences of proclaiming your love for someone who is already in a relationship or the personal toll it takes on someone who is wracked with guilt for developing feelings away from their significant other. This one is a great fit for folks who want to know what they’re getting into but have it be authentic and thoughtful nonetheless.
They Came Together (2014)
Acting as an intersection between the staple rom-com tropes as seen in films by genre stalwarts such as Nora Ephron and the madcap insanity of a Zucker Brothers & Abrahams production, David Wain’s They Came Together is an almost unbelievably funny sendup of the entire ethos of the romantic comedy genre. Riffing directly off Ephron’s You’ve Got Mail, Paul Rudd plays Joel, a corporate executive for a major candy company who is tasked with shutting down the independently-run candy store owned by Molly (Amy Poehler), in order to eliminate the competition. The one nagging issue is that Joel and Molly have begun to fall for each other, leading to a will-they-won’t-they romance by way of totally preposterous inanity.
Wain, no stranger to satire and farce as evidenced by films like Wet Hot American Summer and his work in the sketch comedy group The State, crafts what is arguably his most purely entertaining film by taking the familiar structure and cliches of this type of story and throwing in a stick of absurdist dynamite to see how it shakes things up. Nearly every single line of dialogue, and even every single shot, is built around or punctuated by a never-ending string of ludicrously silly jokes that give the sense of a comedic team not only throwing things at the wall to see what sticks, but to see how much of it is possible to throw at the wall within the span of an 80-minute feature. Rudd and Poehler are supported by a murderer’s row of skilled supporting talent, including but not limited to Bill Hader, Ellie Kemper, Jason Mantzoukas, Michael Ian Black, Christopher Meloni, Ed Helms, and Max Greenfield. And then there’s New York City itself—some would say it’s almost like another character!
Palm Springs (2020)
We seem bound to receive the “person stuck in a time loop” premise grafted onto every genre you can imagine at some point (you’ve got your slasher version Happy Death Day, sci-fi action version Edge of Tomorrow, the original coming-of-middle-age version Groundhog Day, etc.) so it’s just a relief that the romantic comedy angle of Palm Springs ends up feeling so refreshing. Buoyed by a great cast and sense of comedy, this one follows Sarah (Cristin Milioti), in-town at Palm Springs for a wedding who has a hook-up-gone-surreal with another attendee Nyles (Andy Samberg) that leaves her repeatedly living the same day over and over—the same one that Nyles has already been living for a long time now. Resigned to his nihilistic fate, Nyles shows Sarah the ropes of what it means to unburden herself from the existential panic of their situation as the two form a relationship within their shared infinitude. Hilarious and endearing in its depiction of the central relationship and approach to its multifaceted genre construction, Palm Springs is an easy win for a breezy but genuinely good and slightly off-kilter rom-com.
The debut feature of indie coming-of-age wunderkind/newfound film festival darling Cooper Raiff, Shithouse is an assured amalgamation of its influences and more charming than its title may suggest. Landing somewhere between Richard Linklater, Joe Swanberg, and Judd Apatow, Raiff directed, wrote, produced, co-edited, and stars in the film as Alex, a struggling college freshman who is undoubtedly a stand-in for Raiff himself as the film is purportedly an autobiographical account of his struggles during his first year of college. Alex is lonely and dispirited about his prospects for friendship at school, stuck between the competing facts that college kind of sucks but that he also isn’t trying very hard to enjoy it. When a chance encounter with his dorm’s RA Maggie (Dylan Gelula) leads to a Before Sunrise-style walking excursion around the campus grounds that night, Alex finally begins to understand why stepping outside his comfort zone may be worth it.
It sounds trite, but as a debut feature by a 23-year-old, Shithouse is impressive, if slightly directionless. However, there’s an argument to be made that the drifting nature of the plot is representative of this time in Alex’s life, that ever-confusing time when you’ve taken a half-step into adulthood and feel like the world expects you to have it all figured out. It’s sure to speak heavily to the introverted college kids who see themselves represented through Raiff’s character, and it does so with a sense of humor, honesty, and truth that sidesteps some of the more groan-worthy cliches of the genre, finding poignancy where other films would land on banality. Raiff and Gelula are both ultra-endearing and funny performers, and the film navigates both the joy and unease within their night together, as well as its fallout, with an effortlessly relatable tack.