I'll Have What She's Having, Pt. II

The second part of our definitive list of the all-time greatest romantic comedies.

Movies are, in essence, an opportunity to bask in the glow of stars, and no genre boils down that appeal more than the romantic comedy. The original formula—boy meet girl; boy loses girl; boy gets girl—has been complicated and revised countless times, not least by the fact that romantic comedies no longer need to be about boy meeting girl anymore. Still, we will always delight in watching two people fall in love.

A few weeks back, we introduced part I of our definitive list of all-time great romantic comedies. Now, without further ado, here is the second part of our list, covering the last 30 years. Let the arguments commence!

Four Weddings and a Funeral (Mike Newell, 1994)

If you grew up in the early ’90s, and your parents watched films of all kinds, then chances are they caught Four Weddings in the theater and loved it. The British rom-com boasted an ensemble cast including Hugh Grant, Andie MacDowell and Kristin Scott Thomas, following the actors’ characters through a series of romantic ups and downs. Grant bumbles awkwardly, flashing those irresistible blue eyes at the object of his affection — MacDowell, an enigmatic American. But it is Scott Thomas who breaks hearts. She plays one of Grant's best friends and quietly pines for him, knowing her love is unrequited. This comedy contains multitudes. —E.C.

Pulp Fiction (Quentin Tarantino, 1994)

OK, it’s definitely not a romantic comedy. But what if it was? If we separated out the middle portion of this triptych, and ditched most of the guns and violence and mobsters and fake biblical quotations and discursions into the metric system, we would be left with this story of a low-level gangster asked to take out his boss’ wife for a night on the town, where they find themselves lost in a fever dream of the 1950s, complete with milkshakes, ancient hipster slang, and bygone celebrity impersonators. Uma Thurman’s Mia Wallace tells John Travolta’s Vincent Vega about her experience on a long-forgotten television series, and then the two take to the dance floor to the tune of Chuck Berry’s “You Never Can Tell.” Vincent and Mia can never be together, and both of them know it, but for the course of this single peerless dance, they live out a beautiful love story. —S.A.

Before Sunrise/Before Sunset/Before Midnight (Richard Linklater, 1995/2004/2013)

Two beautiful young people meet on Eurail, have a single glorious day in Vienna, and then make plans to meet again in six months’ time. What starts as a charming Eric Rohmer-style romance transforms, over the course of three films, into a disquisition on relationships, aging, and what it means to love another person. By the time of 2013’s Before Midnight, eighteen years later, Ethan Hawke’s face bears witness to the passage of time, with a jagged lightning bolt of worry visible on his forehead as he bids an anguished farewell to his son. Richard Linklater’s trilogy is in love with the everyday glories of conversation, but as it goes along, it also begins to lose faith in the power of communication to heal all wounds. But even now, we still come back to Before Sunrise and root for Celine and Jesse to find each other once more. —S.A.

Clueless (Amy Heckerling, 1995)

Amy Heckerling’s rich-teen fantasia captures the spirit of its unlikely inspiration — the Jane Austen novel Emma — much more effectively than that chilly Anya Taylor-Joy revival that came out a few years ago. [Interruption from Saul: I may have more to say about that further down!] It coined a new lexicon and changed the way we speak. Its cast was wonderfully diverse and included Black, Asian and gay characters among Cher Horowitz’s inner circle, plus a dreamy love interest in Paul Rudd, who played the stepbrother to Alicia Silverstone’s vain shopaholic — but we won’t think about that! It’s so satisfying to watch the bratty blonde, a catchphrase machine, finally realize what we knew all along — that Rudd is “kind of a Baldwin.” As if! —E.C.

Jerry Maguire (Cameron Crowe, 1996)

Cameron Crowe initially wrote his sharp-witted, heartwarming sports movie with Tom Hanks in the title role. Ultimately, he landed his second choice: Tom Cruise, and what a difference that made. While Cruise was synonymous with action films, he knew he had a good thing when he read Crowe’s script, which had zero whiz-bang special effects and high-speed chases. Instead, Cruise got to dig deep into the psyche of a workaholic agent who loses his high-profile job — his identity — and is forced to turn inward and make himself a better man. Enter Renee Zellweger as a cute widowed mom. “You complete me,” Jerry tells her with tears in his eyes. BIG SWOON. —E.C.

My Best Friend's Wedding (P.J. Hogan, 1997)

In this fresh, subversive offering, Julia Roberts went from America’s Sweetheart to Anti-hero. She plays Jules Potter, a jaded food critic, who realizes too late that she wants to marry her college friend Michael (Dermot Mulroney). Her desperation drives her to perform diabolical tricks in hopes of stealing Michael from his wealthy, Stepford fiancée, Kimmy (Cameron Diaz), whom she forces to sing karaoke against her will. Now, a conventional rom-com 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, pals. —E.C.

You’ve Got Mail (Nora Ephron, 1998)

Tom Hanks and Meg Ryan happily reunited for Ephron’s glorious homage to The Shop Around the Corner. It was hardly a faithful remake, as Ephron and her sister, Delia, who co-wrote the script, were loath to mess with the perfection of the original. Instead, they took the enemies-to-lovers story and made it utterly their own. Hanks’ Joe Fox, a corporate robber baron with a hidden marshmallow center, and Ryan’s Kathleen Kelly, the twee children’s bookseller whom he puts out of business, spark a romance in an AOL chat room for people over 30, without realizing they are sworn enemies in real life. —E.C.

10 Things I Hate About You (Gil Junger, 1999)

The absolute best of the Y2K teen-movie boomlet. It’s a modern riff on Shakespeare’s Taming of the Shrew, showcasing Julia Stiles as a righteously angry feminist and Heath Ledger as the bad-boy classmate who melts her icy heart. Stiles is so, so good at being the coolest, most intimidating girl in your English class — she’s bitter, sure, but she’s also aspirational as hell. So many young women distanced themselves from feminism in the late ’90s for fear of being labeled man-haters. Stiles, an Ivy League smartypants in real life, offered proof that a girl could be loved for being unapologetically intellectual and tough-as-nails. –E.C.

Notting Hill (Roger Michell, 1999)

Here, Grant is living the dream. His alter ego, Will Thacker, owns an adorably ramshackle travel bookstore in London’s most charming neighborhood during an era where it was possible for a humble bookseller to occupy real estate there. One day, a gorgeous American movie star steps inside the store. It’s Julia Roberts! No, it’s Julia Roberts playing the fictional Anna Scott, who just wants to live an ordinary life without nosy journalists hounding her wherever she goes. Will provides a safe space for Anna to be herself. He’s got a cozy circle of friends, where Anna has none. He can wear an Oxford shirt with rolled-up sleeves like nobody else. And nobody objects when Anna practically throws herself at his feet. “I’m also just a girl, standing in front of a boy, asking him to love her,” she says. —E.C.

Bridget Jones's Diary (Sharon Maguire, 2001)

Renée Zellweger, an American, managed to win the coveted leading role of Bridget Jones in the big-screen adaptation of Helen Fielding’s bestselling novel about a hapless English “singleton.” The casting raised eyebrows across the United Kingdom: Who does she think she is? She’s from Texas! Zellweger proved the skeptics wrong. She’s one of the funniest rom-com heroines to grace the screen, and while screenwriter Fielding puts Bridget through the wringer, embarrassing her on repeat, she rewards her with a trophy: A debonair, do-gooding attorney named Mark Darcy (Colin Firth). Meanwhile, Hugh Grant has a jolly good time playing the viperish Daniel Cleaver — a character closer to Grant’s real personality.—E.C.

Shall We Dance? (Peter Chelsom, 2004)

Rarely are romantic comedies about marriage. They’re for the young, right? Wrong! Despite appearances, I would classify the swoony Shall We Dance? as a second-chance rom-com about an elegant man experiencing a midlife crisis — hello, Richard Gere! — and the wife (Susan Sarandon) who feels left behind. As lawyer John Clark, Gere takes the train into the city every day, and one night on his commute home, he spots a beautiful dance instructor (Jennifer Lopez) looking out the window of her studio. Intrigued, he leaves the train and finds himself taking dance lessons, which shakes up his dull life. Please watch this movie if only to get to the end, when Gere grabs Sarandon for a spin, set to Peter Gabriel’s “Book of Love.”—E.C.

The 40-Year-Old Virgin (Judd Apatow, 2005)

The over-the-top stuff (Steve Carell getting a surprise chest waxing, or being pursued by Elizabeth Banks’ randy predator) covers up an unexpectedly gooey, emotional center. Andy (Carell) is, of course, the titular virgin, his lack of sexual experience betraying a deep fear. “I respect women,” he tells one of his coworkers. “I love women. I respect them so much that I completely stay away from them." Catherine Keener has never been better as Trish, a 40-something grandmother with an oddly barren eBay-themed store and a messy home life who is willing to be patient with Andy as he figures some stuff out. Apatow’s recurring theme has been how men are both hilarious and broken, and what goes into turning boys (of all ages) into adults. If you like this, try Knocked Up, which swaps in Seth Rogen for Carell and pregnancy for virginity, but is just as funny.—S.A.

The Holiday (Nancy Meyers, 2006)

Nancy Meyers’ satisfying romp offers a dream scenario to women jilted at Christmastime. It is vicariously thrilling to watch Cameron Diaz escape the hustle culture of Los Angeles and her dumb industry ex-boyfriend and take temporary refuge in a sweet cottage in the English countryside, where she meet-cutes Jude Law, a hot widowed dad, and has the grandest, sexiest, Champagne-soaked time. Somehow, Diaz and Law look exactly alike. The best scene: When the two meet up in that cozy little pub as Imogen Heap’s ethereal “Let Go” plays in the background. That’s Nancy Meyers, with her white turtlenecks, bright copper kettles and impeccable casting. She knew exactly what she was doing.—E.C.

Mamma Mia! (Phyllida Lloyd, 2008)

The love saga of Donna Sheridan first began with a hit Broadway musical that made full use of ABBA’s infectious pop songbook. Later, that show was turned into a big, splashy movie starring an extremely game Meryl Streep as single mom Donna, who owns a bed-and-breakfast in Greece. Her daughter, played by winsome Amanda Seyfried, is getting married and wants to invite her father to the wedding, so she sends secret invites to three men with whom Donna was involved in the past. Cue: Colin Firth, Pierce Brosnan and Stellan Skarsgard, each bringing a smolder that makes up for their lack of skill in the singing department.—E.C.

Nick and Norah’s Infinite Playlist (Peter Sollett, 2008)

The character names are borrowed from The Thin Man, but the mood and atmosphere is more Linklater than Powell-and-Loy. Nick (Michael Cera) is still mooning over his ex-girlfriend, but a mixtape he had made for her— “Road to Closure, Vol. 12”—finds its way into the hands of Norah (Kat Dennings), who catches feelings on the basis of a stranger’s musical taste. The will-they-won’t-they compressed timeline marks Nick and Norah as a successor to Before Sunrise, but with a desire to furnish wee-hours Manhattan—even Penn Station! —with a romantic glow.—S.A.

The Proposal (Anne Fletcher, 2009)

The power imbalance of a boss hooking up with her employee might not have aged well, yet we’ll make an exception for Sandra Bullock. If you dropped her on a screwball film set in the 1930s and ’40s, she’d fit right in — and give the likes of Cary Grant a run for his money. In The Proposal, she’s a Canadian-born publishing executive terrorizing Ryan Reynolds, who plays her beleaguered personal assistant. Shenanigans ensue when she loses her visa to work in the U.S., and ensnares Reynolds in a harebrained scheme to pretend to be her fiancé so she can keep her job.—E.C.

Moonrise Kingdom (Wes Anderson, 2012)

If Rushmore was a perverse love story, in which Jason Schwartzman’s manic high schooler and Bill Murray’s depressive businessman competed for the favor of Olivia Williams’ grieving teacher, who ultimately chooses neither of them, Moonrise Kingdom, which might be Anderson’s most underrated film, is an aching depiction of the agony and ecstasy of first love, in which two young runaways escape the pain and conformity of ordinary life and take comfort in a natural landscape that might not be all friendly. Anderson is not to all tastes, but Moonrise Kingdom, for my two cents, is his deepest depiction of love in all its manifold versions, from romantic to parental to unrequited.—S.A.

Silver Linings Playbook (David O. Russell, 2012)

Like many newish rom-coms these days, this one is stealth — meaning that the “rom” is stuffed inside a larger story that pulls focus. In the case of Silver Linings Playbook, that story is Bradley Cooper’s character’s battle with mental illness and its effect on his family. While Cooper struggles to rebuild his life, and win back his ex-wife, he meet-cutes a fascinating young widow (Jennifer Lawrence), who persuades him to enter a ballroom dance competition. Obstacles arise on their path to Happily Ever After, but all is resolved on the dance floor — one of the best endings in the rom-com canon.—E.C.

Saul: I really wanted to like this movie, and I loved David O. Russell’s early work like Three Kings and Flirting with Disaster, but the manic intensity of this one and later films like American Hustle left me kinda cold.

Top Five (Chris Rock, 2014)

No one ever talks about Top Five. Indeed, Chris Rock’s first big foray into genre stardom came and went without making a dent. Parts of it offend, specifically the jokes that read homophobic. But most of the jokes land, and there is ample heart to balance the rowdiness. Rock wrote and directed the film with the confidence of a veteran comedian who knows exactly who he is and what he wants. His character, an actor and recovering alcoholic, falls for a journalist (Rosario Dawson) doing a profile on him. Will he break his engagement to a reality TV star (Gabrielle Union)? (What do you think?)—E.C.

The Big Sick (Michael Showalter, 2017)

Has there been a better joke in a 21^st-century movie than when Ray Romano, playing the father of Kumail’s (Kumail Nanjiani) girlfriend Emily (Zoe Kazan), awkwardly asks him to define his stance is on 9/11. “Anti,” he tells them, chewing a French fry in a colorless hospital cafeteria. “It was a tragedy. We lost 19 of our best guys.” Judd Apatow had established a model for a new kind of romantic comedy with The 40-Year-Old Virgin, and here Nanjiani and Showalter make something sweet and tart and terrifying in equal measure out of the real-life story of Nanjiani and his now-wife (and cowriter) Emily V. Gordon, although whether his girlfriend’s cancer diagnosis or her uncomprehending parents is scarier remains an open question.—S.A.

Always Be My Maybe (Nahnatchka Khan, 2019)

In 2016, Ali Wong and her friend, actor Randall Park, launched a campaign to make their own version of When Harry Met Sally. Netflix soon acquired the project and hired Nahnatchka Khan to direct it. Wong and Park play childhood friends Sasha and Marcus, who stop speaking after a spontaneous teenage hookup. 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. It is obvious that they have feelings for each other, but Marcus is dating a local hippie (Vivian Bang) and Sasha is having a fling with Keanu Reeves, parodying himself as a New Age eccentric.—E.C.

Long Shot (Jonathan Levine, 2019)

Wait, Charlize Theron as a presidential candidate and Seth Rogen as her speechwriter-turned-lover? While it would seem as though those two would never hook up in real life, Long Shot will have you persuaded that Theron is deeply in love with Rogen — give it a chance, and you’ll see why she swoons for him. Refreshingly, Rogen embodies a new kind of rom-com leading man. He eagerly shares the spotlight with Theron, tees up raunchy jokes in her honor, and supports her ambition to be America’s first woman president. Imagine that! (Long Shot should be screened in schools to prevent boys from becoming Reddit-obsessed incels.)—E.C.

Emma (Autumn de Wilde, 2020)

What if Jane Austen…but Wes Anderson? Like sour cream and onion, Autumn de Wilde’s lush, arch, geometrically exquisite adaptation of Austen’s novel brought together two tastes you did not know would perfectly blend together. The scrupulously exacting choreography and camera angles suggest that de Wilde is attracted to the opulence of Austen’s world, but this, too, is a fakeout. Emma., like its spiritual forebear Clueless, is far more interested by what happens when that perfection gives way to messy human emotions, like confusion, joy, and love. Emma. was also a coming-out party for future Furiosa star Anya Taylor-Joy, who has never been better than as this young woman shocked to her core by romance.—S.A.

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