Top 10 Romantic Comedies
After some painful break-ups and brief hookups with possible mates (sorry it didn’t work out Never Been Kissed), we ultimately found true love with our final Top 10 Rom-Coms.
Will you have what we’re having? We’re wishin’ and hopin’ you do.
10. Return to Me
You’re probably thinking: “What’s Return to Me?” Written and directed by the actress Bonnie Hunt, it stars Minnie Driver and David Duchovny as two people struggling to relaunch their lives—she after a heart transplant and he after the death of his wife—when their fates intertwine in surprising ways. The movie’s secret sauce: a grounded and deeply humane love story mixed with leavening comedy from the supporting cast (Jim Belushi and Bonnie Hunt really shine together, as does Robert Loggia and his poker-playing crew). It’s one of the most unheralded rom-coms (and Chicago movies) of the last 25 years, with a Dean Martin-inspired soundtrack and a trip to Italy thrown in for good measure. —Chad Comello (streaming, libraries)
9. My Best Friend’s Wedding
Sure, we could have gone with pretty much any of the other iconic Julia Roberts ‘90s rom-coms here. But then this list wouldn’t have had: a restaurant full of people singing “I Say A Little Prayer” or Rupert Everett in a movie-stealing supporting role or—most importantly—an incandescent Julia Roberts pulling off the ultimate movie star power move of making Jules one of the most likable villains in cinema history. “Getting what you deserve isn’t fair!” Jules laments during the climactic post-kiss chase scene. Indeed, we don’t deserve such a subversive and scintillating entrant into the rom-com pantheon, but by God there’ll be dancing because of it. —Chad Comello (streaming, libraries)
8. Harold and Maude
In a film centered around death, we’re given the joyous and life-affirming songs of Cat Stevens. In a film featuring a death-obsessed teenager, we’re given his lively and eccentric 80-year-old muse. Director Hal Ashby’s brain is one of cobwebs and confetti, and it’s through this lens that the quirky and singular Harold and Maude shines. At first blush, it can take a minute for their age-defying relationship to process as being anything other than innocent and sweet. But when it finally clicks that they have fallen in love, it’s as lovely and heartwarming as any love story put to screen. —Kevin Prchal (streaming, libraries)
7. The Apartment
With an attempted suicide, workplace exploitation, and philandering aplenty, The Apartment might be both the saddest and horniest rom-com of all time—if indeed it could even be considered one, as it strains the very definitions of romance and comedy. And yet that’s precisely why Billy Wilder’s 1960 classic (and Best Picture winner) needs to be on this list: it’s the anti-rom-com rom-com, a gimlet-eyed tour through the emotional wreckage that cheap love can create. But it also lands on its feet, hopeful about what true connection can bring to those who survive the journey. —Chad Comello (streaming, libraries)
6. Forgetting Sarah Marshall
A romantic comedy that pulls off being one of the more charming comeback comedies, Forgetting Sarah Marshall is an unusually sincere and entertaining glimpse into relationships ending and the restoration that takes place after the agony. The movie is a genuine comedy, but below its vigorously absurd humor, easygoing raunch, and lyrical quirks thumps a perceptive, weighty, and ultimately triumphant heart. Directed by Nicholas Stoller and written by Jason Segel, the movie spotlights the impact of a romantic split between Kristen Bell’s Sarah Marshall and Segel’s Peter Bretter. Leaving Peter destroyed, the separation finds the composer hoping for some means of healing his busted heart. Rushing to Hawaii, Peter ends up at the same hotel as his former girlfriend where all kinds of comical antics shake loose. There is an elevated silliness to these antics, but they never seem contrived or stupid in the interest of stupidity. The whole story is rooted in an atmosphere of heavy heartbreak. The movie itself is in no way really gloomy, but it acknowledges the private importance of romantic misfortune and underlines the laughs with completely recognized, if brief, poignancy. —Natalie Bauer (streaming, libraries)
5. The Philadelphia Story
Somehow this modern, feminist rom-com—featuring an all-star cast and touting a 100% on Rotten Tomatoes—is rarely talked about yet still resonates 80 years later. In this 1940 Oscar-winning screen version of the Phillip Barry stage play, Katherine Hepburn gives arguably the best performance of her career as the socialite Tracy Lord. The day before Tracy’s second wedding, the reappearance of her ex-husband (Cary Grant) and a couple of tabloid journalists (James Stewart, Ruth Hussey) threatens to break down the unapproachable façade she hides behind. Grant and Stewart play off of each other hilariously, especially when they are ad-libbing, and Hussey is striking in her honest and relatable portrayal of the photographer who prefers to stay behind-the-scenes. It’s equally scandalous and sophisticated, pushing the boundaries for films of that era and elevating the genre. —Natalie Pohorski (streaming, libraries)
4. When Harry Met Sally
Can a man and woman ever just be friends? When Harry Met Sally, the quintessential romantic comedy, explores the answer. The backdrop for the film, penned by Nora Ephron, is re-enacted interviews with actual older couples about how they met alongside Harry and Sally’s story, which alternates between the most dry and outrageous humor and deep wisdom about love and relationships. The witty banter is its crowning jewel, giving us some of the most iconic scenes in cinema, including the fake orgasm in the deli, the dinner party Pictionary scene, the football game wave scene, and of course the New Year’s Eve finale. But the heart of the film is the quirkiness of the characters. Harry and Sally, and Jess and Marie, each have their own eccentricities that others may see as faults. And at first they drive the other person crazy, but eventually these quirks reinforce just how special they are. —Natalie Pohorski (streaming, libraries)
3. My Big Fat Greek Wedding
My Big Fat Greek Wedding succeeds on so many levels that it’s no wonder how it became (and remains) the highest-grossing romantic comedy of all time. It’s personal: based on the writer Nia Vardalos’ one-woman play, the movie leans hard into the specifics of her life and family, which only makes it more universally relatable. It’s fresh: making any movie is hard, let alone an indie production celebrating a cinematically underrepresented ethnic group, but that’s all the more reason to make more movies like this. And boy is it funny: my thanks to the late Michael Constantine, aka Gus, for several catchphrases I still deploy occasionally, including “put some Windex on it” and “so there you go”. Whether your family is more Miller or Portokalos, you’re welcome at this big fat party of a movie. —Chad Comello (streaming, libraries)
2. You’ve Got Mail
“Don’t you just love New York in the fall?” I do. Especially when it’s paired with a quick, clever, and lyrical script; a near-perfect soundtrack carried by everyone from Randy Newman to The Cranberries; and the lightness and strength of the most iconic romantic pairing to ever grace our movies. But all of these elements aside, none of it works without the singular power of director Nora Ephron. A power that acknowledges the complicated nature of humanity while presenting it in its sweetest, funniest, and most endearing form. It’s not quite my favorite romantic comedy, but with every rewatch, it makes a strong Hanks/Ryan-sized bid to put all the others out of business. —Kevin Prchal (streaming, libraries)
1. Moonstruck
A treasure, because there is really no other movie like it. A combination of avant-garde, satire, and loudmouthed honesty, Moonstruck eventually blends into a sentimental farce that is resoundingly abnormal yet passionately meaningful. Cher won an Oscar for her piercingly comic shift as Loretta Catorini, a spirited, aggrieved widow fixing to begin a dull union with an older fellow (Danny Aiello) just before she happens upon his tragic younger brother, Ronny (Nicolas Cage). Cher nabbed the Oscar because she absolutely does sell her portrayal as Loretta here. She’s got such an effective character that the movie can’t be observed as sexist. She might argue as though she’s got no command over returning to Ronny, but let’s be fair: her behavior is calling bullshit on that every step of the way. Her all-embracing blame and antiquated outlook on matrimony and faithfulness aside, she’s the one with all the power here: she’s the one who first urges to go up to Ronny’s apartment. She always has the upper hand. She’s not Ronny’s prize and there’s not at any point in the movie a juncture where a few dumb disagreements hinder the plot. And this performance she brings to life here, which is entirely a result of her magnetism and not her cadence or sensationalization, is the heart of this movie. —Natalie Bauer (streaming, libraries)