Career Arc: Tom Petty

Wrestler, Statesman, Hostage Negotiator, Legend: The Life of Antonio Inoki

The Rom-Com Hall of Fame: Champions and Challengers

Weighing the candidacies of the all-timers, the almost-weres, and the Heigls of the genre

It’s been 25 years since the birth of the modern romantic comedy. Beginning with When Harry Met Sally… in 1989, the genre has become a launching pad for some actors and a refuge for others. In these movies we find predictable moments, heightened notions of love, and a lot of questionable outfits. And while the genre has morphed over the years, we’re still in love with rom-coms — so we’re celebrating them all week. Welcome to Rom-Com Week. Today, we look at the titanic figures of the modern rom-com and the players who never quite reached the mountaintop. 

MEG RYAN SLEEPLESS IN SEATTLE (1993)

Champion: Meg Ryan

Wesley Morris: With a good star, there’s a continuum. Based on the beginning and middle, you can imagine an end. And romantic comedies trace a perilous arc. You can do two or three before the idealism turns to dust. It’s tough work, devoting yourself to the dramatization of falling in love, because the genre refuses to let you stay there. Hepburn was on a continuum with Tracy, Astaire with Rogers, Doris Day with Rock Hudson. Meg Ryan was on a continuum with society. She was single in the modern sense, striving at first for idealism, then for her dignity.

She began her run as Sally Albright, an avatar for Nora Ephron’s explanatory candor. This is how you mail a letter. This is how you order a salad. This is how you fake an orgasm. It wasn’t the moaning and thrashing that made her a star in that deli scene. It was the purity with which she picks up her fork and puts it in the lettuce. What decorum. A year later (1990), she wound up with Tom Hanks in Joe Versus the Volcano. The few people who saw them together probably had the same thought: “$$$$.” Ryan and Hanks were old Hollywood souls, and the two movies Ephron made with them were set against classical backdrops: An Affair to Remember for Sleepless in Seattle and The Shop Around the Corner for You’ve Got Mail.

That these two have made only three movies together feels like a rip-off. They are right for each other, even when what Ephron has them do at the end of You’ve Got Mail is notoriously wrong. But Hanks had different gears, which makes you wonder whether Ryan’s attempts to find gears of her own — as a depressive good-time girl, an alcoholic guidance counselor, and the first woman to (posthumously) receive the Medal of Honor — was, in a sense, a way of keeping up with him. And she maybe she could have kept trying, but a chameleon star like Nicole Kidman (never the same role twice), honed in on at least some of Ryan’s dreams of actorly seriousness.

In any case, despite understandable attempts to diversify, her brand was love, and you could feel the search for it turning her bitter. You can even feel it in the sweetness and whimsy of something as terribly made as 1994’s I.Q. But the idea of waiting atop skyscrapers for Hanks and falling for peak-of-his-powers Billy Crystal is one thing. Flying to Paris in order to get back the fiancé who dumped you over the phone (1995’s French Kiss) or teaming up with a stranger to get revenge on your cheating partners (1997’s Addicted to Love) is something else. It’s sadder. Her principles had gone dark, her clothes were disheveled, her body hard, her hair hacked off. In 1998, she was reduced to dating an angel and the man who wants to put her bookstore out of business. By 2001, it was a dude imported from another century. To see her drunk and sloppy or acutely sexualized — in Hurlyburly or In the Cut — was to experience a star’s allergic reaction to herself.

Ryan is the most important person to make romantic comedies in the last 40 years. You can see the disappointment, the desperation, and the disillusion. The genre used her up. To paraphrase one of her TV sisters, Charlotte York: Ryan had been doing this for 13 years; where was he? The rebooting had taken its tragic toll. Her continuum wasn’t just any romantic comedy. It was Groundhog Day.

JULIA ROBERTS MY BEST FRIEND'S WEDDING (1997)

Champion: Julia Roberts

Shea Serrano: Julia Roberts, in totality, is unstoppable. Just a handful of stats:

  • Since 1989’s Steel Magnolias, she has been in 39 films.
  • Her 13 most popular movies have grossed more than $3 billion at the box office worldwide.
  • She has been nominated for more than 100 awards, including four Academy Awards, two of which were for Best Actress. (She was nominated in 1991 for Pretty Woman, and won 10 years later in 2001 for her role in Erin Brockovich.)
  • In 2003, she broke what was then a record for an actress’s pay in a movie, earning $25 million for starring in Mona Lisa Smile, which is basically more than two and a half times Tim Duncan’s salary today.
  • She’s been on People’s “50 Most Beautiful People in the World” list ELEVEN times, the same number as Halle Berry and 11 times more than anyone reading this article.

But her place on the romantic-comedy spectrum is even more impressive, her influence causing the walls of the genre’s Hall of Fame to vibrate. At her most dominant, Roberts cranked out a historic and unmatchable near-10-year stretch of lordship, starting with 1990’s Pretty Woman and ending with 1999’s Runaway Bride, highlighted by a God Level three-movie stretch of dominance from 1997 to 1999 with My Best Friend’s Wedding, Notting Hill, and Runaway Bride that will likely never occur again. Never. Like, NEVER.

Really, the only person who has ever come even a little close to that is the lovely Sandra Bullock, whose three best romantic comedies (While You Were Sleeping, Miss Congeniality, and Two Weeks Notice) came over a seven-year period from 1995 to 2002. But comparing Bullock to Roberts in rom-coms is, to crib a line from My Best Friend’s Wedding, like comparing Jell-O to crème brûlée. She just never quite managed to match Roberts’s likability, preternatural humor, or warmth, let alone her onscreen governance. Plus, you probably have to take off at least a few points from Bullock’s cumulative score for overplaying her hand in 2005 with the poop storm Miss Congeniality 2: Armed and Fabulous. I’m saying, a portion of Roberts’s prestige would’ve for sure been scrubbed off if she’d green-lit Pretty Woman 2: Back to Hooking or whatever, right?

At any rate, Roberts is unassailable. She is a romantic-comedy masterpiece, the perfect mix of aw-shucks charm, intelligence, and beauty, all pulled together by a 64-tooth smile that’s as flawless as anything has ever been. Remember “I’m just a girl, standing in front of a boy, asking him to love her”? Remember “I would rather have 30 minutes of wonderful than a lifetime of nothing special”? Remember “I love you. I’ve loved you for nine years, I’ve just been too arrogant and scared to realize it, and … well, now I’m just scared”? Remember “BIG mistake. Big. Huge! I have to go shopping now”?

It’s a wrap.

Roberts for life.

SANDRA BULLOCK TWO WEEKS NOTICE (2002)

Champion: Sandra Bullock

Juliet Litman: What is Sandra Bullock’s most iconic movie? There’s a case to be made for The Blind Side since it won her an Oscar. Speed put her on the superstar path. Gravity is another contender, as both a massive critical success and a technical landmark. And Sandy’s particular experience on that film has already been mythologized. She endured a notable amount of discomfort during filming to execute Alfonso Cuarón’s vision, and all parties involved say she handled it with grace and kindness. Of course she did. This won’t be a surprise to anyone who takes a long view of Ms. Bullock’s career. Her warmth is the engine of all the romantic comedies that have peppered and defined her career since the mid-’90s. She may never have received the best material from heavyweights like Richard Curtis or Nancy Meyers, but she didn’t need it. Her rom-coms are largely just about her immense likability.

She began her foray with While You Were Sleeping in 1995, playing a token booth employee for the CTA in Chicago. Her job was primarily outside, so she wore a multitude of hideous wool hats in winter. I’m not quite sure if the headgear was a remnant of the misguided ’90s or if this was unique to her character. No matter; her radiant smile managed to conquer the sartorial horror. The movie came early on, but this was probably the most winning performance of her career. Granted, she had the luxury of playing opposite Bill Pullman, an actor with his own considerable charisma in 1995, but she carries this movie on her own. She’s in every single scene! Most impressively, even when she has lied to Pullman’s character’s extended family about being engaged to their comatose son, and then successfully convinces said son that he is an amnesiac who has forgotten her,  you never stop to think, Wow, this woman and this movie are fucking nuts. You’re too enchanted.

The ability to sell an audience on a patent absurdity is her greatest triumph, and it’s why I think her rom-com achievements distinguish her from other titans like Meg Ryan and Julia Roberts. In spite of her questionable movie choices (she even won a Razzie in 2010), she has maintained a career that we generally think of favorably. We’re all rooting for her. I wish I could have been in the pitch meetings that got Michael Caine, Candice Bergen, peak Benjamin Bratt, William Shatner, and Sandra Bullock to sign on to Miss Congeniality. Yes, the movie turned out to be a delight that condescended only to a certain segment of women, but its success is mostly because of Sandy. She gently cajoles us to go beyond the suspension of disbelief and fully discard any notions of plausibility. Even though she has no known friends, she quickly earns the trust of the other women and there’s no reason to question it. This is the Sandra Bullock Show. Accept it, go with it. Her romantic comedies are all about trying on different identities, even if her experimentation with being a sellout lawyer in Two Weeks Notice is a little more high-concept than when she pretended to be engaged to Ryan Reynolds in The Proposal. While all the other rom-com stars are trying to sell us a heightened truth, Sandy is out here making her own truth, and that’s all that matters.

THE OBJECT OF MY AFFECTION. Image shot 1998. Exact date unknown.

Challenger: Jennifer Aniston

Bill Simmons: I’m old enough to remember when Friends was pegged as a Courteney Cox vehicle. Every guy in my age range adored Cox, dating back to her tomboyishly watershed appearance in Springsteen’s “Dancing in the Dark” video. We rooted for her when she dated Alex P. Keaton, and we rooted for her when she kept cranking out lousy movies and canceled TV pilots. But after Friends blew up overnight, poor Courteney somehow ended up with the show’s most boring character (Monica, an absolute dud that first season) as castmate Jennifer Aniston blossomed into The Hottest Woman In America. So long, Courteney.

In my lifetime, I can only remember four actresses taking off as abruptly as Aniston did: Bo Derek (10, didn’t last), Julia Roberts (Pretty Woman), Sharon Stone (Basic Instinct) and Aniston during that first year of Friends. Shit, her HAIRDO became its own American phenomenon. Jen was gorgeous enough to be out of your league but not so staggeringly beautiful that you didn’t have a chance, either. Of all the attainably hot female celebrities in my lifetime, she’s right up there. Every guy in his mid-twenties honestly believed that he could have sweet-talked 1994-95 Aniston at the right wedding or party … no matter how broke he was. She seemed cool and funny and sweet, and she didn’t seem like someone who lived on coffee and cigarettes like every other actress. That was her appeal over everything else. Well, other than her curves.

And as Friends turned into a ratings juggernaut that first season, Aniston morphed into the surest of sure things to become a major movie star. The mid-1990s had already evolved into the golden era of rom-coms, with Hollywood mining every premise hinging on a career-oriented single babe who couldn’t find love unless she did something craaaaaaaaaaaazy. Instead of making a rom-com for her first big movie, Aniston swerved the other way — she played the sexually frustrated wife of That Guy From The Geico Ads in 1996’s She’s the One, a casting decision that made sense only because he was cheating on her with an In-Her-Prime Cameron Diaz. I once wrote that watching Mid-’90s Aniston and Mid-’90s Diaz on the same 50-foot screen was like watching Montana and Rice together, and I’m not sure that was hyperbolic enough.

But Jen would have been better off playing Diaz’s part (the vixen troublemaker with no redeeming qualities), and not just because that love triangle unwittingly foreshadowed the rest of her career. She could have replaced Julia as America’s Sweetheart; that was never happening if she came out of the gate bragging about her vibrator and wondering when she was ever getting laid again. That should have been her second or third movie, not her first big one. From there, she overcorrected the other way, pursuing the unofficial rom-com belt by releasing two rom-bombs in a row.

In 1997’s Picture Perfect, Jen played a career-driven single woman who needs a date for her boss’s wedding because … wait, this movie wanted us to believe that Jennifer Aniston was single for three seconds in 1997? What? Jen believed she would get fired if her boss thought she was single, when actually she was wasting her time hooking up with a despicably horny Kevin Bacon. He played the oily office Lothario who does everything short of dropping Rohypnol into her drink before they hook up. (Apologies if that’s a deleted scene on the DVD.) Since she can’t bring Bacon to the wedding, she convinces a photographer (played by Jay Mohr) to pretend to be her fiancé at the wedding, only he falls for her, only they have to pretend to break up at the wedding … I mean, there’s a good chance that this movie single-handedly caused someone to create Jezebel.

One year later, she released an even more repugnant rom-com called The Object of My Affection. The plot: A pregnant but impossibly skinny Jen starts developing feelings for her gay buddy (played by Paul Rudd) and decides she wants to raise her baby with him. It’s like someone saw the ending to My Best Friend’s Wedding and said, “What if we blew this out into a whole movie?” This movie managed the rom-com double no-no of offending women AND gay people, which would have been like Friday Night Lights somehow offending all football fans and everyone from Texas.

And that was that for Jen’s quest for the rom-com belt. Instead, she became massively famous and comically wealthy, changed her iconic hairstyle, lost some of her curves (an American tragedy, if you ask me) and fell for the even more massively famous Brad Pitt. When he jettisoned her for Angelina Jolie, Jen was suddenly starring in a real-life rom-com way more interesting than any fictional one she made — you know, the one about the gorgeous A-lister who famously lost her man to a deviously gorgeous A-lister, then found herself sentenced to the cover of Us Weekly for the next five years. Everyone loved that movie. We couldn’t get enough of it. She finally had her triumph, even if it came eight years too late. Nearly two decades later, she’s engaged to the dude from The Leftovers and still headlining mainstream movies, which is more than anyone else from the 1990s can say except for the Cal Ripken Jr. of rom-coms (Sandra Bullock). Still, the great Jennifer Aniston never held the unofficial belt. It’s kind of impossible.

KRISTIN SCOTT THOMAS & HUGH GRANT FOUR WEDDINGS AND A FUNERAL (1994)

Champion: Hugh Grant

John Lopez: In Four Weddings and a Funeral, a bespectacled Hugh Grant stammered into the limelight, apologetic and profane, like a rakish Harry Potter ready to seduce our girlfriends with adorable facial tics. It was as if he’d sprung fully formed from the head of writer Richard Curtis, the Zeus of the British rom-com. But Grant had actually enjoyed a long gestation period on U.K. screens (including a woefully underseen turn in Roman Polanski’s Bitter Moon) before hitting Anglophiles the world over with the gale-force winds of his stutter. At long last, Grant had conquered the Atlantic. For the true measure of Grant’s caddish charm, just remember that he single-handedly sold that rain-soaked closing kiss with Andie MacDowell — he made himself iconic by snogging a woman who’d cheated on her fiancé with him, only moments after he’d left his own bride at the altar. Twenty years later, Four Weddings holds up far, far better than your typical romantic blockbuster; and on some level, Hugh Grant will always be that “git who’s only slept with nine people” spilling his heart out in Partridge family lyrics. His quirks were still fresh, light, and modulated, not yet fodder for keen impressionists and late-night monologues.

That would come soon enough. One year later, in fact, when Grant invaded America — and an LAPD holding cell. The mythos of Hugh Grant and Divine Brown’s Sunset Boulevard blow job has been so deeply etched into our cultural hive mind, you forget that Grant was here promoting his American debut, Nine Months: The mind still boggles at anyone cheating on Elizabeth Hurley like that. Honestly, Leno squeezing that squirmy mea culpa from Grant probably gave Grant’s career the bigger boost. (It definitely helped Divine Brown.) You may be tempted by a great cast: Jeff Goldblum, Julianne Moore, and Joan Cusack, all there to support Grant in his leap across the pond. But you’re better off rewatching the Leno interview. Never has one movie paid for so many vacation homes.

It’s like all the greatest sins of the ’90s were combined in a single film: Hugh Grant, Tom Arnold, and Robin Williams with a Russian accent. Within moments, Arnold is fighting his dog over Grant’s beluga caviar; and before you ask, yes, there was a Rollerblading/ear-piercing montage. A Marxist might call it the most sinister kind of late-capitalist pablum meant to lull the masses into aspirational stupor: Grant plays a child therapist who can afford both a Porsche and a stunning San Francisco apartment with bay views. (On the plus side, you get quintessential Jeff Goldblum lines such as “I denied her my essence.”) Yet much like bad Indian food, Nine Months stays with you. When you’re going through your first pregnancy, doctors will tell you that if your water breaks, it’s not a life-or-death race to the hospital “like in the movies.” This is “the movies” to which they refer. Comedy doesn’t get much broader than the 20-minute slapstick finale. Grant injures a hostess, a pedestrian, and a biker en route to the hospital with Julianne Moore in labor; then he fistfights Arnold over taping Moore’s and Cusack’s simultaneous births. But nothing, not even Tom Arnold with a camcorder, could hold Grant back now. His superstar status had been cemented by two of the greatest back-to-back performances a romantic leading man has ever given: proclaiming his love to Andie MacDowell and apologizing to Jay Leno.

BRIDGET JONES'S DIARY (2001) RENEE ZELLWEGER, COLIN FIRTH BJDI 073

Champion: Renée Zellweger

Steven Hyden: Earlier this month, principal photography commenced for The Whole Truth, a legal thriller starring Keanu Reeves as a defense attorney who is enlisted to a defend a 17-year-old boy accused of murdering his father. Jim Belushi plays the boy’s father, and Renée Zellweger is the mother. It is Zellweger’s first film since 2010. I am 95 percent sure that I’m not going to see it.

Zellweger will always be a ’90s phenomenon. She is the Deep Blue Something of rom-com leading ladies, and Jerry Maguire is her “Breakfast at Tiffany’s.” Elsewhere she applied her alt-rock brand of glamour to playing regular, downtrodden folks thrust into extraordinary situations (Cold Mountain, Nurse Betty, Chicago) or the wives or girlfriends of those folks (Me, Myself, and Irene; Cinderella Man). In the Bridget Jones films, she played a lovable fuck-up who was more or less benign, like Courtney Love on the right kind of drugs. Zellweger’s specialty was depicting a curated version of “reality” with a cute, radio-friendly facade. Zellweger seemed more authentic than the typical movie star, and also less consequential. Renée Zellweger didn’t have the gravitas of Julia Roberts, but you could plausibly imagine going to a Julia Roberts movie with Zellweger.

Her high point is, was, and always will be “You had me at hello.”

I admit I was in love with Zellweger for a while there after Jerry Maguire. I was 18 and hadn’t yet learned that Renée Zellweger as I knew her didn’t exist. She was a mirage of “approachability.” She was one of Cameron Crowe’s Implausibly Charming And Supportive Band-Aids, giving Tom Cruise the confidence he needed to defeat Jay Mohr. She lived to admire Cruise and his inspirational memo, to act as his helpful little-sister figure when he needed a helpful little-sister figure, and then downshift into “sexy personal assistant” mode once her wisecracking son went to bed. She was just sitting there — an impossibly perfect amalgam of neediness and strength — waiting to complete a man. What (young and callow) dude wouldn’t want that?

Now Zellweger is playing Jim Belushi’s wife. Deep Blue Something has broken up. But we’ll always have that moment.

THE WEDDING PLANNER MATTHEW MCCONAUGHEY, JENNIFER LOPEZ WEPL 061

Challenger: Jennifer Lopez

Mallory Rubin: Jennifer Lopez has been earning screen credits for nearly three decades and star treatment for nearly two, and like almost any celebrity who’s assaulted our eyeballs and ear holes that many times over that many years, she’s also earned our admiration and admonition in near equal measure. Yet it’s hard to dispute the reign that Lopez enjoyed from 2001 to 2002, a two-year fairy tale between the bookends of distaste and despair she forever carved into her Internet tombstone with The Dress in 2000 and The Movie in 2003.

Lopez was a formidable multi-talent threat in 2001 and 2002, enjoying simultaneous success in theaters and on the pop charts. She launched her own clothing line. She got engaged to Ben Affleck. She became the first female artist to have the no. 1 album and no. 1 movie at the same time, with J.Lo and The Wedding Planner in January 2001. She didn’t quite repeat the feat with This Is Me … Then and Maid in Manhattan in 2002, but they were successful enough for J.Lo, Cultural Force to endure.

While those pre-Gigli days might seem like a distant memory, it’s important to acknowledge and even celebrate the impact that J.Lo had during that two-year run. For a little while, she was anywhere and everywhere, and we wanted her to be. She had a rare and impressive ability to be a hellcat in her music videos and an Everywoman (albeit an exceedingly pretty one) in her movies. In The Wedding Planner, her character helps make everyone else’s dreams come true, but can’t find love in her own life; she’s not even always the bridesmaid, but rather the sad sack who makes sure the bridesmaids don’t have toilet paper on their shoes or broccoli in their teeth. In Maid in Manhattan, she is quite literally a maid in Manhattan, cleaning up after rich assholes in a fancy hotel, suffering through the humiliation so that she can earn an honest living as a single mom. In both movies, we’re asked to believe that someone with that face and that body might really be alone in this world, but she manages to convince us, manages to pull off the wrong-time-wrong-place sob story and both ends of the rags-to-riches arc. She also manages to play opposite Matthew McConaughey and Ralph Fiennes, and find chemistry with both. It’s not quite as impressive as making sparks fly with Rust Cohle and Voldemort. But it’s close.

There’s a line in Maid in Manhattan that is at once exceedingly simple and eternally adaptable: “Tonight the maid is a lie. This is who you really are.” And that’s exactly the point. For two years, J.Lo could be whomever rom-com aficionados needed her to be. She could lock eyes with a soon-to-be senator across a crowded banquet hall or fall in love with a doctor over M&Ms. She could win their hearts, and ours. She could make a claim to rom-com greatness, even if it was a lie.

REESE WITHERSPOON PATRICK DEMPSEY SWEET HOME ALABAMA (2002)

Challenger: Reese Witherspoon

Andy Greenwald: Rom-com heroines are supposed to melt. It’s the unavoidable turn after the third-act twist: Our love-starved lead, bedeviled by indecision and tripped up by plot, turns to the just-a-boy standing in front of the just-a-girl and drops her defenses. Her eyes widen, her lip trembles, her heart decides. In a word: She melts. (That this is also the key attribute of processed cheese is not a coincidence.)

Reese Witherspoon, despite her candylike first name and buttercream appearance, does not melt. It’s against her nature even to soften. When circumstances demand surrender, her features contort more in panic than in bliss. There’s a moment early on in Sweet Home Alabama in which a pre-McDreamy Patrick Dempsey (playing a sort of Cuomoish, Kennedyesque scion) sneaks Witherspoon’s Melanie Carmichael (née Smooter) into Tiffany’s to dazzle her with a surprise proposal. When the lights snap on and the dozens of retail workers who’d better be getting generous overtime beam contentedly, Dempsey drops to one knee. And Witherspoon’s face looks less overwhelmed than overcome — with nausea, specifically. Her eyes bug out of her skull like she’s just taken a swig of rotten milk. She looks embarrassed for everyone. Even the audience.

Sweet Home Alabama was a huge hit when it was released 12 years ago, but it has aged abominably: A movie about a successful fashion designer should make at least some small effort to be fashionable; a film about the moral superiority of Southerners ought to endeavor to treat them as something other than amusing cartoons. Still, it offers tremendous insight into Reese Witherspoon’s many gifts as well as her highly specific limits. She’s the rare actor whose gear-grinding, teeth-gnashing drive is inseparable from her appeal. (Another? Tom Cruise.) Her best roles — Tracy Flick in Election, June Carter in Walk the Line, Ride or Die Wife No. 1 in this — involve no compromise and very little swooning. That’s why the only part of Alabama that makes sense is the opening, in which Witherspoon’s Melanie pulls an all-nighter at her company’s lovably distressed Soho loft (sure), is air-kissed by her fabulously gay, mock-turtleneck-wearing African American mentor (uh-huh), and generally treats Fashion Week the way Sherman treated Atlanta.

Once Dempsey takes a knee, though, Witherspoon’s agency goes out the window. Returning to her “colorful” hometown in a rented Saab, she’s more or less an asshole. Conceding to the inevitability of her childhood romance, she’s more or less a sap. The fact that Reese is constitutionally incapable of falling to pieces is what makes her interesting. It’s also what makes her a terrible fit for rom-coms and why her presence on this list is so brief. She doesn’t do well as a target. You don’t want to get her. What you want is to get out of her goddamn way.

DREW BARRYMORE 50 FIRST DATES; FIFTY FIRST DATES (2004)

Champion: Drew Barrymore

Mark Lisanti: I suppose we could talk about Drew Barrymore right now. You could pull up a chair, bring over a couple of lattes from the barista bar, and we could settle into a mutally satisfying conversation about 50 First Dates, which many might consider the high-water mark on Barrymore’s rom-com résumé. (“Above The Wedding Singer?” you gasp, spilling coffee down your Van Halen T-shirt, then go back to your Fandango purchase of Blended tickets.) Or about how Barrymore almost certainly has the most interesting career of anyone on this Hall of Fame list, having matured before our eyes from doe-eyed child actor to still-doe-eyed-but-with-a-hint-of-hard-won-wisdom star-cum-mogul.

But let’s talk philosophy instead. Because I’m working on a crackpot theory you may be interested in, because you’ve just read about 6,000 words about rom-coms to even get to this point.

In the Hegelian dialectic, thesis gives rise to its antithesis, resolving in synthesis. You may have learned this in high school or college. Or on Wikipedia if you followed this link like I just did. Let’s not pretend we all can’t use a refresher course in the core principles.

In the Heiglian dialectic, reesis gave rise to her antidrew, resolving in katherinsis. Let me explain.

Following 2002’s Two Weeks Notice, anchored by two of the all-time greats in Sandy Bullock and Hugh Grant, the universe entered an age of great Rom-Com Uncertainty. Into that void stepped Sweet Home Alabama’s Reese Witherspoon, a flinty, driven heroine fresh off the career-redefining hit of Legally Blonde, ready to seize the moment laid at her feet. And seize it she did: After dispensing with a terrible Blonde sequel, she was right on her way to an Oscar in Walk the Line.

So consider 50 First Dates–era Barrymore the universe’s antithesis, a spiritual course correction to a much gentler rom-com presence. Whereas Witherspoon displayed awards-worthy chops and the obvious desire to graduate out of the genre, the retired wild child Drew — scion of a legendarily debauched Hollywood clan who’d had her in the game since toddlerhood — had settled comfortably into a second romantic Adam Sandler vehicle. There’s not a single awards play until Grey Gardens in 2009. She was content to rom-com it up and collect enormous producing fees, because by then she’d already had life figured out, knowing Oscars aren’t as important as seven- and eight-figure checks.

Which brings us to our synthesis. Imbued with Reese’s restless drive and Drew’s ability to appear in a movie with Judd Apatow’s bros without hanging herself before the wrap party, Katherine Heigl emerged from 2007’s surprise juggernaut Knocked Up pre-exasperated with the limitations of the form and with the rom-com megastardom that would immediately follow. You’ll read more about her from a Heigl superfan in a moment, but there you have it: a perfectly well-reasoned and philosophically sound argument based mostly on the fact that all three actresses were blonde in the mid-aughts.

I rest my case, your honor.

Knocked Up year 2007 director Judd Apatow Katherine Heigl

Disruptor: Katherine Heigl

Chris Ryan: It’s kind of weird how Heigl went from top 10 to not mentioned at all, but in the end I think it came down to Katherine Heigl not having much interest in playing Katherine Heigl for the rest of her life. The dual “controversies” of wanting more from Grey’s Anatomy and wanting better than Knocked Up had her painted as an ungrateful malcontent. She had the kind of two-year run that most actresses would sacrifice their firstborn to Ari Emanuel for — playing the female lead in Knocked Up and starring in 27 Dresses and The Ugly Truth. The former was a classic ugly Cinderella tale about someone who is always the bridesmaid, while the latter was a gambit at The Sweetest Thing–style raunch-com. Both were commercially successful, and Heigl probably could have kept making variations on those movies for the next 10 years.

My thing with Heigl, aside from just generally finding disagreeable people pretty interesting, is that her very disdain for the things she was good at made her good at those things in the first place.

Now, don’t get me wrong, she could sell an insane tear-jerking Grey’s moment better than almost anyone else on that show. To this day, Dr. Izzie remains the realest shit Shonda Rhimes ever wrote, even if she went out like a ball of crazy. She provided moments of calm in the “always doing a bit” mania of Knocked Up — and I actually think later Judd Apatow movies would have been better off with more people like her and fewer people like Seth Rogen. In her starring vehicles, Heigl played a convincing idealist in Dresses among the real-talk twins, Judy Greer and Krysten Ritter. And even though it’s a pretty stupid movie, she held her own against Gerard Butler’s “LOL misogyny” pundit in The Ugly Truth.

Despite the above, the reason I like Heigl, and the reason she was not long for this rom-com world, and maybe even the reason why you could make a case for her being the last great rom-com star, is that she broadcasts something so rare in these kinds of flicks. It’s just barely there, but you can see it in the way she looks at Rogen, Butler, Ed Burns, Malin Akerman, and James Marsden. It’s a look, a feeling that says, “This shit is beneath me.”

Because let’s be honest: The scenarios of most of these movies should be beneath most people! Some jack-wagon gets you pregnant but wants to maintain his suspended boyhood instead of stepping up to the plate? Some throat-cutting newspaper writer wants to follow you around and do an article about you attending a lot of weddings? You have to work with Gerard Butler? All this stuff would be pretty insulting to deal with. They say there always needs to be a character in a movie that represents the audience, and I agree. Heigl’s contempt for her material may have been what undid her career, but it’s also the thing I like most about her.

After The Ugly Truth, her career has kind of swerved, and now she’s playing a sanitized Carrie Mathison in State of Affairs. She wanted to be Erin Brockovich, but she didn’t want to have to play Julianne Potter five times to get there. “I love romantic comedies,” she said recently. “But maybe I hit it a little too hard. I couldn’t say no. I stopped challenging myself. It became a bit by rote and, as a creative person, that can wear you down.”

To paraphrase Charlize Theron in Prometheus, a queen has her reign, and then she dies. It’s inevitable. Katherine Heigl was never going to let it get to that point.

LOVE ACTUALLY (2003) COLIN FIRTH LACT 005FOH

Challenger: Colin Firth

Louisa Thomas: Colin Firth is a stuttering prince, a cuckold, a cad. He is a grieving gay professor. He is “a sad-eyed British artist holed up in a rundown hotel in small-town Vermont after being dumped by his fiancée.” He is Amanda Bynes’s father. He is a singer in a spiked collar. But at the end of the day, it is a truth universally acknowledged that Colin Firth is Mr. Darcy.

You may object to Mr. Darcy’s inclusion in the Rom-Com Hall of Fame. You may protest that the BBC adaptation of Pride and Prejudice is not a romantic comedy. You may be right! Jane Austen’s novel, after all, was a satire published in 1813, and the 1995 BBC series ran for nearly six hours. And yet. Our claim is based on four minutes out of those six hours, a scene that did not appear in the book: Mr. Darcy strips off his jacket, dives into a murky pond, breaststrokes through some weeds, and then, after striding across his estate, wet and rakish, comes upon Elizabeth Bennet (Jennifer Ehle), who has already fallen in love with his massive house. He stumbles awkwardly, charmingly, through pleasantries. “Oh yes of course,” he half-says, half-swallows, and millions of hearts respond, Oh yes of course. He is so British. So aristocratic, arrogant, vulnerable, witty, and deeply, deeply repressed. So handsome, in an almost comically exaggerated way: the melting soft eyes, the pronounced chin, the broad shoulders, the raffish hair. In his britches and muttonchops, he is the landed gentry as drawn by Disney. The pond scene became so iconic that it became bigger than itself. Last year, the moment in which Mr. Darcy emerges from the water was voted “the most memorable moment in British TV drama.” The catch: He is never shown emerging from the lake. The most memorable moment in British TV drama never happened. But memories create what memories desire. A romantic comedy was born.

“Just nipped out for fags prior to getting changed ready for BBC Pride and Prejudice,” the Mr. Darcy–obsessed Bridget Jones writes in her diary in Helen Fielding’s best-selling novel Bridget Jones’s Diary. “Hard to believe there are so many cars out on the roads. Shouldn’t they be at home getting ready?” In the movie version and its sequel (Bridget Jones: The Edge of Reason), Colin Firth ingeniously plays Mark Darcy, who happens to be the misunderstood-but-inevitably-true love of Bridget Jones (Renée Zellweger). Hugh Grant also stars. Romantic-comedy bingo!

Has any such talented and multifaceted actor been so totally identified with one name as Colin Firth? No number of Oscar nominations for more serious roles can erase Mr. Darcy. “Every single film since [Pride and Prejudice] there’s been a scene where someone goes, ‘Well I think you’ve just killed Mr. Darcy.’ But he is a figure that won’t die. He is wandering somewhere. I can’t control him. I tried to play with it in Bridget Jones. I’ve never resented it: if it wasn’t for him I might be languishing,” Firth once told The Times, “but part of me thinks I should do this postmodern thing, change my name by deed poll to Mr. Darcy.” Oh yes of course.

THE BEST MAN (1999) TAYE DIGGS, SANAA LATHAN BTMA 005

Challenger: Sanaa Lathan

Rembert Browne: Sanaa’s career arc is interesting. Because you think of her as a staple figure in a hefty string of romantic, majority-black-cast comedies in the late ’90s and early ’00s. But then you look back at her films and realize that she wasn’t. There were only two, The Wood and The Best Man, both released within four months of one another, in 1999.

Yes, there were only two, but these are two defining films of an era. And she was in both. Two movies that seemed to employ half of Young Black Hollywood during the time had one female overlap, Sanaa Lathan. Romantic comedies are what gave her a career.

But then you begin to get caught up. And you start calling Love & Basketball and Brown Sugar “romantic comedies” (a mistake many, many people make). Because you want more black rom-coms. Because there are few things whiter than a compiled list of “Best Rom-Coms.” And because it’s nice to think that black people can fall in love and also laugh.

But Love & Basketball and Brown Sugar just aren’t. They’re rom-drams. You don’t want that one year to represent Sanaa’s entire rom-com output, up until The Best Man Holiday 14 years later, because it really felt as if she did so much more. But that was really it. After The Best Man, romantic comedies and Sanaa Lathan diverge, with her next, most notable run being the leading lady opposite a string of early-’00s leading black actors (Omar Epps in 2000’s Love & Basketball, Wesley Snipes in 2000’s Disappearing Acts, Taye Diggs in 2002’s Brown Sugar, Denzel Washington in 2003’s Out of Time). And then, of course, another not-romantic-comedy-that’s-often-referred-to-as-a-romantic-comedy-even-though-at-best-it’s-dramedy, 2006’s Something New.

There are a number of reasons for why Sanaa didn’t make a stronger push for romantic-comedy greatness. One of those is probably because she was rising in prominence around the same time as her Out of Time costar, Eva Mendes. Who knows, were Eva not around, maybe Sanaa would have gotten Hitch and then become the next big thing. Who knows? But the other reason is that she simply didn’t make any more. It sure felt like it, though. And for that, she deserves some credit, somehow convincing the public that she is synonymous with an entire era of rom-coms. But if there’s ever a conversation about the Rom-Dram Hall of Fame, she’ll be waiting. Because that was not only her best run, but also her one true run.

GWYNETH PALTROW EMMA (1996)

Challenger: Gwyneth Paltrow

Emily Yoshida: I’ll go ahead and get it out of the way up front that I am emphatically not a rom-com person. But I’m in good company, because neither was Gwyneth Paltrow, really. She’s theoretically on our also-ran list for that Oscar she won for Shakespeare in Love, cinema’s most up-its-own-ass romantic comedy that a group of adults somehow decided was the best movie of the year. (I’ll spare you a full-length Shakespeare in Love rant, but having just rewatched it for research purposes, I have been freshly reminded of the thick cloud of smug farts that permeates it. Anachronistic gags about Elizabethan England are the lowest form of humor, and I want to murder Joseph Fiennes’s bad-boy-bard biker jacket.) That Oscar, and the ensuing, legendarily gaggy acceptance speech, more or less officially took Gwyneth out of that select pool of Julias and Renées — down-to-earth, relatably quirky Everygirls whom you wanted to root for as they pratfell in love. Seeing her thank her famous parents over tremulous yet perfectly dictated sobs in that pink Ralph Lauren prom dress made it hard to imagine going out and grabbing a cocktail with her and your gal pals (a stance I would argue we should reconsider).

People who dislike Paltrow as a performer often conflate her rich-girl public persona with the emotional restraint of many of her characters. Which is neither fair nor inaccurate — warmth and humanity have never been her strong suits onscreen — but not everyone can or should be that kind of star. And Gwyneth has proven capable of commanding a romantic comedy on her own terms, using her natural chilly presence to position herself as a kind of brittle, oblivious straightwoman just begging to be knocked off her high horse. She’s pretty perfectly cast in Emma, for example. It was 1996, and Peak British Gwyneth (British Gwyneth got a LOT of work in the ’90s) busybodied her way through Jane Austen’s love-letters-and-archery-practice universe with just the right combination of wit and cluelessness. Appropriately, the film came out just a year after the cultural takeover of the Emma-based Clueless, and was somewhat amusingly promoted as “Clueless with carriages,” which it never really lives up to. But it was a reminder that Gwyneth could have fun onscreen; that she was willing to let us laugh at the self-righteousness of her characters and, by proxy, her already somewhat precious public persona.

In her comedic work, Paltrow always kind of looks like she’s been dragged there against her will; she’s not an inherently high-energy presence. But that’s what I like about her! We don’t root for her to get what she wants, necessarily, we root for her to let go of something. (There’s a little Margot Tenenbaum in almost every Paltrow character, which I suspect has something to do with why Paltrow characters have been few and far between since The Royal Tenenbaums.) She’s best as the girl pinching her temples with annoyance as some rakish rogue takes her and shakes her by her bony shoulders, which is why she and Robert Downey Jr. have found such sublime, babbling highs as Tony Stark and Pepper Potts. Actually, I amend my opening statement: I’m not a romantic-comedy fan, unless you count the Iron Man movies.

WARNING: This photograph can only be reproduced by publications in conjunction with the promotion of the above film. For Editorial Use Only.Comment se faire larguer en 10 lecons How to Lose a Guy in 10 Days Comment se faire larguer en dix lecons Annee 200

Challenger: Kate Hudson

Molly Lambert: Kate Hudson is frustrating. If she had never been cast as Penny Lane in Almost Famous after Sarah Polley dropped out, we wouldn’t know that she was even capable of being great. She might just be another famous person’s daughter with a decent vanity acting career; Hudson’s biggest credits prior to Penny Lane are 200 Cigarettes and Gossip. But because she is so great in Almost Famous, it’s hard to watch her be merely serviceable in terrible movies like, let’s say, oh, How to Lose a Guy in 10 Days.

I recently started watching How to Lose a Guy in 10 Days, which I had never seen before, with an open mind. Surely Hudson and Matthew McConaughey (at his blondest and blandest) could generate sparks. But the movie only made me feel upset, mostly that I was so bored. I don’t hate formulaic romantic comedies. I watch 27 Dresses every time it’s on cable, and I once owned the soundtrack to My Best Friend’s Wedding on cassette. But HTLAGI10D checks off rom-com boxes joylessly. Hudson is the type-A white woman who works for a women’s magazine run by an Anna Wintourian steely bitch played by Bebe Neuwirth. Everyone lives and works in a New York that is never recognizable as New York, sort of like the New York in The Strain. 10 Days was so dull that I was praying for the eye-worms to show up. I felt mad at the inane plot device that requires both main characters to lie and be two-dimensional weirdos who in no way resemble human beings. I was mad that I cared that Matthew McConaughey’s character’s family lives on Staten Island but all have Southern drawls to match his. I was mad that this movie wasted Adam Goldberg, Kathryn Hahn, and Thomas Lennon, whose quirky supporting characters didn’t even get any good jokes. And I was mad at myself for being mad, for having anything invested in whether romantic comedies are successful as romances or comedies, let alone both.

Even though Kirsten Dunst’s character in Cameron Crowe’s Elizabethtown may have been what inspired Nathan Rabin to write his original Manic Pixie Dream Girl piece, Almost Famous is essentially a conscious deconstruction of the trope before it was even named. One of Almost Famous’s main arcs is William Miller coming to realize that even though he automatically realizes the Band-Aids are human beings, the guys in Stillwater he’s been idolizing all this time behave otherwise. It would never occur to William to think of women as disposable commodities you could trade for beer or pass around like one. He thinks of them as his friends. Almost Famous revolves around Hudson’s performance, which has the effervescence of her mom, Goldie Hawn, in Shampoo with something of a sharper edge. The Penny part may not have been written with her in mind, but it fit Hudson like a thrifted fur-collared coat. She imbues Penny Lane with a down-to-earth quality that balances out her ethereality, as her performative enthusiasm for life turns out to be the usual attempt to compensate for how shitty life can sometimes be, particularly in supposedly glamorous worlds like ’70s rock touring.

Hudson is so cool in Almost Famous that it’s always a shock to see her in rom-coms playing complete squares, boring cookie-cutter blondes whose smiles feel smug rather than charming. Hudson’s ideas for sabotaging the burgeoning relationship with McConaughey are things like putting boxes of maxi pads in his bathroom cabinet and being too picky to eat a lavish meal he cooked for their date. By the end of their 10 days, I felt as though I had aged a thousand years. HTLAGI10D opens with Hudson’s journalist character, Andie Anderson, working on a serious piece about Tajikistan that has been rejected by her editors, with a dangled promise that she’ll be allowed to write about more serious issues for her Cosmo-clone mag if she pulls off the titular ploy for a story. It’s an interesting setup, raising issues of art, commerce, and personal credibility. For a minute I thought this movie was going to be amazing. But then it collapses into a totally regular bad rom-com that can’t even be saved by a climactic Carly Simon sing-along between the two stars. Even that part made no sense, because a Marvin Hamlisch cameo is set up moments before. (Though it did inspire me to revisit the oeuvre of Marvin Hamlisch!) How to Lose a Guy in 10 Days is unfortunately, then, a micro-encapsulation of Kate Hudson’s whole career: an auspiciously great and fizzy start and then a whole lot of flat soda in the form of mediocre rom-coms like Raising HelenYou, Me and Dupree; and Bride Wars.

The last time I saw Kate Hudson be funny and charming and engaging onscreen was in an episode of The Rachel Zoe Project wherein, no lie, I thought to myself, Wow, Kate Hudson seems really chill and fun to hang out with. She’s got movies coming out this year directed by Barry Levinson, Peter Capaldi, and, uh, Zach Braff. Hudson doesn’t exactly need to prove that she still has the chops she demonstrated in Almost Famous. She’s still rich, second-generation famous, and has children with rock stars. Maybe she’s happy just to hang out in Malibu, eat quinoa, and walk around in the swash. We’ll always have Penny Lane. 

Illustration by Andy Friedman

Filed Under: Rom-Com Week, Julia Roberts, Sandra Bullock, Katherine Heigl, Hugh Grant, Colin Firth, Renee Zellweger, meg ryan, Jennifer Aniston, Jennifer Lopez, Sanaa Lathan, Reese Witherspoon, drew barrymore, Rom-Coms, Gwyneth Paltrow, kate hudson

Follow

Get every new post delivered to your Inbox.

Join 376,329 other followers