Romantic comedies ranked by Entertainment Weekly reviews

Romantic comedies, you had us at hello. We’ve been living, laughing, loving with this genre for decades now, and what a wild ride it’s been. Even though our own lives have been starkly devoid of meet-cutes, high-stakes secretive bets, and endearingly snarky best friends, these pillars of film have been more than enough entertainment to suffice. In celebration of our extra special (big fat) untold stories issue, we dug into the archives to rank some of our favorite flicks by their original EW critics’ reviews. Because love hurts, but rom-coms don’t have to.

From the review: “This dogged attachment to a romanticized social conservatism may fit our current political climate and the retro fantasies of teenage girls, but it undermines the occasional charms of such a graph-plotted romantic comedy, which suffers particularly in inevitable comparison with My Best Friend’s Wedding. Where Julia Roberts turned the world on with her huggability, Jennifer Lopez‘s vibe is that of someone afraid to get mussed. And where Rupert Everett was divine as a sidekick, Matthew McConaughey is mortally ordinary as a main dish who spends most of his time smiling like a party guest.” —Lisa Schwarzbaum

From the review: “Sleepless in Seattle is bound to be hailed in some quarters as corny, romantic, and old-fashioned, and for good reason: The movie is so prefab, so plastically aware of being ‘corny,’ ‘romantic,’ and ‘old-fashioned,’ that it feels programmed to make you fall in love with it. It would seem that Nora Ephron thinks in cliches: She mixes old ones from Hollywood with new ones from pop-psych therapy. When Harry Met Sally… was like one of Woody Allen’s urban valentines turned into a TV series, and Sleepless lacks even that movie’s intense peppering of jokes — it’s like a ’50s tearjerker synthesized by microchip.” —Owen Gleiberman

From the review: “If Lindsay Lohan never makes it back to leading-lady status, then we can all comfort ourselves with the knowledge that we have Emma Stone. In Easy A, a remorselessly cheeky sociological teen-raunch comedy that attempts to do for The Scarlet Letter what Clueless did for Emma, Stone has a speed and sparkle that may remind you of Lohan in her Mean Girls prime.” —Owen Gleiberman

From the review: “Back in 1999 The Best Man was an outrageously fresh comedy of love and backbiting, and not just because it marked Hollywood’s belated discovery that characters could be upscale and African-American at the same time. The movie had wit, verve, spark, and surprise. But writer-director Malcolm D. Lee shouldn’t have waited 14 years to do a sequel.” —Owen Gleiberman

From the review: Friends With Benefits is like a Rock Hudson/Doris Day gabfest for the hookup generation. The dialogue has an insanely pop-culture-fixated shoot-from-the-brain chattiness. Mila Kunis, with her big doe eyes, is like Brigitte Bardot gone Sex and the City, and Justin Timberlake has a uniquely charming rhythm: He’s laid-back and in overdrive at the same time. Even so, there’s a weirdly fluffy flaw at the film’s core. It keeps telling us that Dylan is “emotionally unavailable” and that Jamie is “emotionally damaged.” But all we see are two characters so gorgeous and winning, they can afford to take their appeal for granted. Ultimately we’re asked to feel their romantic pain, but the film was a lot more enjoyable, and convincing, when it looked like they didn’t have any.” —Owen Gleiberman

From the review: “Jane…returns to her picture-book Santa Barbara home. She walks into her magazine-layout kitchen. And, no joke, the audience goes ooooh. Look at the gleaming copper pots hanging from a ceiling rack (where’s my Williams-Sonoma catalog?)! Look at the bowl of luscious magenta plums (must stop at Whole Foods)! Ogle that sexy long farm-style table made for complicated cooking and convivial eating (Crate & Barrel? Nah, must be something custom-made)! Get a load of that stuff!

It’s Complicated is middle-aged porn, the specialty of Nancy Meyers, who also set ladies and interior decorators drooling over homes and gardens in 2006’s The Holiday. Specifically, the movie is middle-aged femme porn. Not that there’s anything wrong with that, au contraire, but let’s understand one another: This is a fantasy about a triumphant ex-wife (Meryl Streep) desired all over again by her ex-husband (Alec Baldwin). And for icing on the gâteau, she’s admired by a second cute, successful, eligible man, too—played by Steve Martin, no less! This is the stuff of Santa Barbara book-group literature.” —Lisa Schwarzbaum

From the review: “10 Things I Hate About You may be the cheekiest ‘literary’ update yet — a post-riot grrrl gloss on The Taming of the Shrew, with Shakespeare’s plot twirled around devices that have become cliches, virtually overnight, in the new teen comedies: the guy who struggles to land a girl in order to win a bet; the ingenue—in this case Kat’s younger sister, the button-nosed Bianca (Larisa Oleynik)—who’s a virgin to everything but consumerism. ‘There’s a difference between like and love,’ says Bianca. ‘I like my Skechers, but I love my Prada backpack!’ —Owen Gleiberman

From the review: “Something old, something new, something borrowed — all helped My Best Friend’s Wedding succeed, but it was something blue that made it stand out. In a time when most romantic comedies end with strangers bursting into applause as the characters kiss, My Best Friend’s Wedding dared to end on a disappointment. While not a tearfully downbeat climax, it was definitely bittersweet — and proof that even in such a time-honored genre, there’s always room for something fresh.

Something real, too. Because just as Julia Roberts‘ almost-altared state in the film sounded vaguely reminiscent of her leave-’em-at-the-altar private life, her character’s scene-by-scene humbling — as she goes from pretentious aesthete to realistic woman — seemed like a reconstruction and restoration of the actress herself. Forget those flirtations with heavy period drama. Never mind Hook and Dying Young. My Best Friend’s Wedding was good old Jules again, her wide smile intact. Back with the fans who love her best. And till death do them part.” —Stephen Witty

From the review: “The mess, though, where’s the mess? The hysteria, the middle-of-the-night jitters of loneliness? The mess of Bridget’s (Renée Zellweger) life has been tidied, neatened into little piles of mirth and gaiety. The script, by the formidably bright team of Helen Fielding, Andrew Davies (another pretzel — he adapted that BBC Pride and Prejudice), and Richard Curtis (Four Weddings and a Funeral), grins and cracks wise with pop-cultural jokes and the pretty production values that made Four Weddings so appealing: Bridget’s idea of a cozy evening is watching Frasier on the telly in her flannel pj’s, and her idea of terror is a literary cocktail reception at which she has to make small talk with Salman Rushdie.” —Lisa Schwarzbaum

From the review: “As fiercely clever and proudly profane as Amy Schumer‘s Comedy Central show has been this season, there can be something a little self-serving in her humor. Over and over again, the punchlines come at her own expense — how she drinks too much, sleeps around too much, and doesn’t conform to Hollywood’s size 0 ideal. But it’s hard to tell whether she actually believes what she’s saying or if it’s all an act, a way of winning the audience over through self-deprecation. That’s a pretty tricky tightrope to walk, but Schumer has managed to walk it with the skill and fearlessness of a Wallenda. Now she’s parlaying her deliriously dirty postfeminist brand of feminism into a bid for movie stardom in Judd Apatow’s new comedy, Trainwreck. If the gambit works (and the film’s so sharp and funny, it’s impossible that it won’t), the mind reels at how Schumer will deal with big-screen success in her shock-therapy stand-up act. After all, how do you take a shiv to Hollywood’s sexism and size 0 piggishness after you’ve become its latest darling?” —Chris Nashawaty

From the review: “Finally, a fresh answer for the next time some fusty Freudian coughs up the old challenge, What do women want? After basking in the skin-tone-flattering candlelight of the wish-fulfilling romantic comedy Something’s Gotta Give, my indisputable response is we want what Diane Keaton is having.” —Lisa Schwarzbaum

From the review: “[Love, Simon] feels less like filmmaking than peak TV, with its strenuously current references (Drake, Jon Snow, a family dog named Bieber) and CW-ready Simon (Jurassic World‘s Nick Robinson). Still, the writing is sharp, even if the story is cushioned in a sort of self-acceptance bubble where everyone is adorable and actualized and essentially safe. In many ways, Simon is queerness with all the sharp edges and scary bits sanded down. But the movie also speaks to another kind of privilege, one that straight kids have had since movies began: the right to a romantic fantasy served up like ice cream, tart and sweet.” —Leah Greenblatt

From the review: “Jerry Maguire is the story of how Jerry, cut loose from his identity, gently stumbles into a new kind of life. For a while, I expected a familiar sermon about a top gun who finds, like, his integrity, man. After all, how is Jerry going to satisfy his ego now? By writing fiction? Cameron Crowe, however, has something subtler in mind. Jerry (Tom Cruise) still wants to be a sports agent. He just wants to slow down, to reconnect with his clients — with himself. Jerry Maguire doesn’t have a conventional narrative drive, and that’s part of its charm; it’s a movie of quick feints and jabs. Jerry dumps his fiancee and sets up shop with Dorothy (Rene Zellweger), a single mother so inspired by his mission statement — and his dimples — that she quits her job as an SMI bookkeeper to go to work for him. Jerry, likewise, hangs on to just one client, Rod Tidwell (Cuba Gooding Jr.), an upstart wide receiver for the Arizona Cardinals who stakes his shot at superstardom on Jerry’s undivided loyalty.

To be or not to be — a human being, that is. That’s the question that courses through nearly every scene of Jerry Maguire. America’s favorite star is still on smiling Cruise control, but now he finesses it into a dance. He seduces — then steps back; he turns on the charm — then lets it slide into pools of doubt. It’s Cruise’s deftest performance yet as a slickster grasping for the decency in himself. As Dorothy, Renee Zellweger, with her oval face and slightly daffy little-girl voice, at first calls up images of a more petite Victoria Jackson, but she grows on you. When she turns her imploring stare on Cruise, she melts through his sheen the way Debra Winger melted through Richard Gere’s in An Officer and a Gentleman.” —Owen Gleiberman

From the review: “Move over, Julia Roberts. Jennifer Garner has a smile that’s a big, lush, wide-screen dazzler, with voluptuous candy lips that nudge her face into dimples as lovely as they are long. I’m not sure if Garner has grinned three times on Alias, but in 13 Going on 30, she takes on the role of Jenna, a scrawny, MTV-addicted nerd who finds herself occupying a woman’s body, and she has an enchanting yet friendly radiance. She wraps the audience in an embrace of lost innocence.” —Owen Gleiberman

From the review: “The infectious charm and sunny goodwill of Four Weddings and a Funeral can so immediately buoy a soul ravaged by winter weather and winter movies about pet detectives that said soul may happily find herself halfway into the second wedding before the meaning of the Gershwin tune as sung by Elton John at the start of this bright, British romantic comedy begins to resonate fully: ‘For every happy plot ends with a marriage knot/But there’s no knot, no not for me.'” —Lisa Schwarzbaum

From the review: “The picture is full of moments to savor, whether it’s Jacob (Ryan Gosling) telling the schlubby Cal (Steve Carell) to ‘be better than the Gap,’ or Cal and Emily (Julianne Moore) reuniting for a parent-teacher conference (the scene all but vibrates with the years they’ve shared together), or Hannah (Emma Stone) and Jacob’s touching postcoital murmurings, or the Big Romantic Speech at the end — a conventional moment, to be sure, except that the hard-won, battle-weary affection of Cal’s words left me in tears. One of the movie’s motifs is Cal’s decades-old line about Emily: ‘She’s the perfect combination of sexy and cute.’ Crazy, Stupid, Love. is the perfect combination of sexy, cute, wise, hilarious, and true.” —Owen Gleiberman 

From the review: “In the first 90 seconds, one of Lloyd’s (John Cusack) friends advises him to stay away from Diane Court (Ione Skye), the object of his desire, noting ‘We don’t wanna see you get hurt.’ ‘I want to get hurt!’ replies Lloyd. I don’t know a single guy who doesn’t identify with Lloyd’s tongue-tied anguish, or a gal who doesn’t swoon at the memory of Lloyd’s boombox serenade. The film’s only flaw, and one previously seen in Better Off Dead and 1985’s The Sure Thing, is that Cusack’s love interest isn’t one tenth as interesting as he is. Why would Lloyd go gaga over the pretty but boring Diane when the available, acerbic Corey (Lili Taylor) is in the corner strumming her guitar?” —Mike D’Angelo

From the review: “The one that’s giddily brilliant is the women’s trip to Vegas for a bachelorette party. The entire sequence consists of the plane ride out there, and it’s a tour de force, culminating in Annie’s (Kristen Wiig) tranquilizer-fueled tirade against her rival (Rose Byrne). It’s at this point, when Annie gives in to all the masochistic craziness that she’s been feeling, that Bridesmaids begins to leave every cookie-cutter ‘chick flick’ miles behind.

Yes, the film is a romantic comedy, in which Annie meets a sweet Irish cop (Chris O’Dowd) and must figure out how to let her guard down. But its deepest romantic subject is the complicated friendships between women. Once she decides to stop being nice, Annie starts spreading disaster, and there’s something very gratifying about seeing her lash out at this wedding, this life, and this lifelong soul sister, all of whom she thinks have left her out in the cold. She’s an Everywoman you can believe in, showcased in the kind of deft comedy of feminine passion — where deep despair meets Wilson Phillips — that a great many people have been waiting for. Now that Wiig and company have built it, will they come?” —Owen Gleiberma’

From the review: “(500) Days is like a mood ring cued to the ups, downs, and confusions of modern love. It’s a Gen-Y Annie Hall made by a new-style Wes Anderson who uses his cleverness for humanity instead of postmodern superiority. None of it would work, though, without such lived-in performances. Zooey Deschanel makes the lovely, sensuous Summer just precocious enough to know what she wants without coming out and saying it, and Joseph Gordon-Levitt, with his junior Springsteenian chin jut, lets you read every glimmer of hope, pain, lust, and befuddlement beneath his nervy facade. It’s a feat of star acting, and it helps make (500) Days not just bitter or sweet but everything in between.” —Owen Gleiberman