The Best Romantic Comedies Ever Made

My favorites, featuring schmaltzy, spicy cameos from Cary Grant, Julia Roberts, Seth Rogen and Ali Wong, among other genre stars.

“I’m just a girl, standing in front of a boy, wearing casual flip-flops with a pencil skirt to win back the love of my life.” ICONIC. (Source.)

Hello friends!

I hope you had a nice, cozy holiday weekend, wherever you were. I’ve had a lot of new subscribers recently, so I wanted to take a second to introduce myself again.

I’m Erin Carlson, a journalist and author living in San Francisco’s North Beach neighborhood, an urban hellscape filled with unleashed labradoodles, hot-pink Bougainvillea blooms, and the scent of freshly baked sourdough bread everywhere you go. I write narrative nonfiction books about pop culture and film history, and if you haven’t guessed already, given the content and title of this newsletter, I love romantic comedies. Earlier this fall, my latest book, No Crying in Baseball: The Inside Story of A League of Their Own, became a USA Today National Bestseller. Previously I wrote Queen Meryl: The Iconic Roles, Heroic Deeds, and Legendary Life of Meryl Streep, and I’ll Have What She’s Having: How Nora Ephron’s Three Iconic Films Saved the Romantic Comedy. I referenced the latter in “The Meg Ryan We Remember,” which was included in Substack Reads last week.

The other night, I was annotating I’ll Have What She’s Having for someone who won a copy in a silent auction, and on a blank page, I added a list of my Top Ten romcoms. “I should do this for the Substack,” I thought, stating the obvious. I’ve sent out holiday and baseball movie picks since starting You’ve Got Mail last December, but not a romcom watchlist! Reader, my silence ends today. Behold my curated vintage and modern favorites, each available to stream:

• Bringing Up Baby (1938): To watch this screwball classic is to marvel at the work of three masters — in the director’s chair, Howard Hawks, and in front of the camera, Cary Grant and Katharine Hepburn. The plot is ludicrous, the banter faster than a high-speed train. Hepburn dazzles as an eccentric heiress (the best kind) who falls for a painfully handsome paleontologist (Grant, duh) and enlists him to help her transport a leopard named Baby to her farm in Connecticut. Hijinks ensue as Hepburn hides Grant’s clothing in a desperate attempt to delay his wedding to another woman. Grant is forced to wear her fur-lined negligée for one scene, and when a stranger at the door requests an explanation, the actor ad-libs, "Because I just went gay all of a sudden!” (Wink, wink.)

• The Shop Around the Corner (1940): Here, Jimmy Stewart and Margaret Sullavan play anonymous pen pals who fall in love over letters but despise one another in real life. And in real life, they’re co-workers competing to sell the most pocketbooks at Matuschek and Company, a leather goods shop based, amazingly, in Budapest. (That enmity was later revived in the 1998 remake You’ve Got Mail.) Working with a script from Samson Raphaelson, director Ernst Lubitsch, famed for his elegant, playful style, delivers one of the great, all-time enemy-to-lover stories. Before he takes us to Happily Ever After, Lubitsch delays the inevitable through a series of misunderstandings and hostile encounters, such as the cafe showdown where Sullavan skewers Stewart in brutal fashion. If she scratched his surface, she says, “I know exactly what I’d find; instead of a heart, a handbag; instead of a soul, a suitcase; and instead of an intellect, a cigarette lighter — which doesn’t work.” Ouch. When Stewart finally reveals his identity in the film’s heart-stopping finale, and the former foes embrace, it feels as if true love was invented in a leather goods shop in Budapest.

• The Apartment (1960): With its dark edge and stylish visuals, Billy Wilder’s Best Picture winner somehow remains fresher and more original than most of what you’ll find in movie theaters today. Those wide shots of desk-bound corporate drone C.C. Baxter (Jack Lemmon) working in an open-floor office? You can imagine them hanging in the MoMA. You can find replicas in the Wes Anderson aesthetic. The storyline features Baxter trying to curry favor with his terrible bosses and move up in the world. He lets them use his Upper West Side apartment (address: 51 West 67th Street) for illicit affairs. Then he learns that one married boss is taking advantage of his crush, elevator operator Fran Kubelik, portrayed by Shirley MacLaine with winsome vulnerability. Cue a crisis of conscience. If The Apartment were to be remade — and why not? — I’d cast Michelle Williams as Fran, and possibly Zachary Levi as Baxter. I know, I know. They’ve been trying to make Zachary Levi happen since 2005. This time, it just might work.

• Coming to America (1988): When I think about this weird and wacky film, I can’t help but smile. It stars Eddie Murphy as an African prince named Akeem who defies his imperious father (James Earl Jones) by rejecting an arranged marriage and moving to Queens to find a queen of his own. He wants to meet an independent woman. Ideally, she would love him for him, and not his status and wealth. Akeem gets a job at McDowell’s, a McDonald’s knockoff, and is soon smitten with Lisa (Shari Headley), the kind, sane daughter of the restaurant’s goofy owner (John Amos). She’s a tough cookie, a New Yorker born and bred, but she sees his sweetness and his joie de vivre, and he wins her over. Meanwhile, Akeem continues his deception and insists that he’s poor — until his family blows his cover. The betrayal stings Lisa. His royal title does not impress her at all; she refuses his hand in marriage. Will she have a change of heart? (It is a truth universally acknowledged that all romcoms require one.) Thanks to Murphy’s comic brilliance and Headley’s understated charm, Coming to America — which made a whopping $128 million in 1980s dollars — remains atop my list for life.

• The Nora Ephron Trilogy (1989-1998): I’m grouping When Harry Met Sally, which Ephron wrote, together with her directorial triumphs, Sleepless in Seattle and You’ve Got Mail. These films are The Godfather of the genre and Ephron the fairy godmother overdoing the twinkle lights (one can have never too many) and crafting dialogue sharper than Taylor Swift’s cat eyeliner. These films are the gold standard. The sum of all wisdom. The answer to any question. How do I find a good apartment in New York City? According to Harry Burns (Billy Crystal), “What you do is look in the obituary section. You see who died, find out where they lived, and tip the doorman.” What should I order at a roadside diner? “I'd like the chef's salad please with the oil and vinegar on the side and the apple pie a la mode,” Sally Albright (Meg Ryan) declares. “But I'd like the pie heated, and I don't want the ice cream on top, I want it on the side, and I'd like strawberry instead of vanilla if you have it. If not, then no ice cream, just whipped cream but only if it's real. If it's out of a can, then nothing.” Doling practical advice, and strong opinions about food, was Ephron’s love language. She left a part of herself in every character she created, no matter how marginal. Her distinctive voice is what makes her trilogy unforgettable.

• My Best Friend’s Wedding (1997): I think we can all agree that Ryan is the undisputed queen of the 1990s romcom but let us not overlook Julia Roberts’ contributions to the genre! Where Ryan put the sweet in America’s Sweetheart, rarely diverting from good-girl roles molded to her actual personality, Roberts channeled a believable villain, despite the fact that she was a down-to-earth hippie IRL. Look no further than Jules Potter, her anti-hero in My Best Friend’s Wedding. Jules, a cosmopolitan food critic, realizes too late that she wants to marry her college pal Michael (Dermot Mulroney, not to be confused with Dylan McDermott). Her desperation drives her to do devilish deeds in hopes of stealing Michael from his wealthy, Stepford fiancée, Kimmy (a game Cameron Diaz), mere hours ahead of their Big Day. Jules is diabolical. She persuades Kimmy to offer Michael, a humble sportswriter, a high-paying job at her father’s company — knowing full well that the gesture will hurt his feelings. She forces Kimmy to sing karaoke against her will. Both attempts at sabotage backfire. Ultimately, Jules atones for her shenanigans by performing her duty as MAID OF HONOR — get a restraining order, Kimmy! — and looking amazing in a violet gown. A traditional romcom would end with Jules marrying Michael. But My Best Friend’s Wedding bucks convention and offers her impeccable gay confidante George (Rupert Everett) as a (very platonic) replacement. The thing is, Roberts can flash that electric megawatt smile, and all is forgiven. That’s charisma, my friends. Our anti-hero has been through the wringer, but you know what? She’s going to be fine. Spin her around the dance floor, George…

• Notting Hill (1999): Roberts’ next romcom was another roaring success. Here, she drops the scheming to play an American movie star (meta) opposite Hugh Grant, who bumbles his way into her jaded heart. She wants to live an ordinary life without the press hounding her wherever she goes; Grant, the owner of a ramshackle London bookstore, provides much-needed normalcy. (Not to mention a close-knit, cozy group of friends, one of whom is the Earl of Grantham from Downton Abbey.) How I adore Notting Hill. It erases the current news cycle and makes me feel happy and safe. I want to live in it! Between the incongruous Shania Twain soundtrack, Grant’s Horse & Hound fib, and the line “I’m also just a girl, standing in front of a boy, asking him to love her,” this one’s for the books.

• The Holiday (2006): The quintessential Nancy Meyers “chick flick.” (For the love of Chardonnay and shabby-chic home decor, I mean that as a compliment.) No filmmaker luxuriates in feminine melancholy quite like Meyers; in The Holiday, the writer-director’s heroines make the seasonal blues look downright aspirational. Kate Winslet and Cameron Diaz swap houses over Christmas as each recover from heartbreak. Winslet moves into Diaz’s dreamy Los Angeles abode and makes instant friends with her elderly neighbor (the wonderful Eli Wallach); Diaz hunkers down in Winslet’s idyllic English cottage and makes google eyes at Mr. Right (the stunning Jude Law). The pub scene remains my favorite, thanks to the sizzling chemistry between Diaz and Law, and the haunting vocal stylings of Imogen Heap.

• Long Shot (2019): I went into this movie with zero expectations. Long Shot was barely marketed by its studio. All I knew was that it starred Charlize Theron as a presidential candidate and Seth Rogen as her speechwriter. Ugh, Seth Rogen. Not him again, I thought. Recall that Seth Rogen headlined the hit Judd Apatow romcom Knocked Up in the mid-Aughts. He played a slacker man-child who has a one-night stand with an uptight E! News reporter that results in pregnancy. He got all the jokes; his leading lady (Katherine Heigl) scowled a lot. Refreshingly, Long Shot presents Rogen as I’d never seen him before. He embodies a new kind of leading man — one who tees up jokes for his partner, and happily supports her dreams and makes them his, too. Both he and Theron are hilarious. Witness Rogen fall down the stairs at a fancy event where Boyz II Men are performing, or Theron successfully negotiate a hostage crisis on psychedelics. I could watch Long Shot a zillion times and never tire of it.

• Always Be My Maybe (2019): The comedian Ali Wong was born to star in romcoms. In 2016, she and her friend, actor Randall Park, launched a campaign to make their own version of When Harry Met Sally. Netflix quickly snapped up the project and tapped Nahnatchka Khan to direct it. Wong and Park play childhood friends Sasha and Marcus, who drift apart following a disastrous teenage tryst. Years later, they reconnect when Sasha, now a famous chef, returns home to San Francisco to open a new restaurant. She finds Marcus still living with his widowed father. The spark rekindles, but alas, each is dating someone — Marcus, a local hippie (Vivian Bang), and Sasha, none other than Keanu Reeves, parodying himself in the best celebrity cameo that ever was. Wong, whose arch humor masks a marshmallow interior, is the closest we’ve come to Nora Ephron.

Last but not least, some honorable mentions: Billy Eichner’s bitingly funny Bros; the Kate Hudson/Matthew McConaughey vehicle How to Lose a Guy in 10 Days; Sandra Bullock and Ryan Reynolds in The Proposal; Adam Sandberg in Palm Springs, and J.Lo in everything.

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