1. Renée Zellweger, Bridget Jones’s Diary (2001)
As romantic comedies come to lean more and more on the twin beams of predictable formula (obnoxious people meet each other, hate each other, then come to appreciate each other) and ridiculous gimmicks (as said people are kept apart by outsized misunderstandings and contrivance), it’s apparently becoming necessary for each new rom-com to distinguish itself by making its characters progressively broader and more cartoony. Which tends to leave audiences without much stake in the proceedings as they wait for the bad behavior of some shrill, irritating caricature to be rewarded with ultimate happiness. Case in point: Renée Zellweger as the title character in Bridget Jones’s Diary, the story of a crude, foul-mouthed, dim-witted, judgmental, childishly petty girl-woman who manages to win the love of multiple men even though she pretty much lives to write horrible things about them in her titular diary. This is a lady who saddles the people around her with mental epithets like “prematurely middle-aged prick” and “fat-ass old bag”; even the man who loves her has to admit “You tend to let whatever’s in your head come out of your mouth without much consideration of the consequences.” Which is an acute problem, since she’s mostly thinking things like “Jesus fuck, my ass is as big as Brazil, but I need a shag anyway.”
2. Meg Ryan, Serious Moonlight (2009)
As the jilted wife being left by her husband (Timothy Hutton) for a younger lover, Meg Ryan inhabits a traditionally sympathetic role in Serious Moonlight—in fact, its entire premise hinges on the idea that audiences will find her attempts to get him back, if not relatable, then at least somewhat charming in their out-there doggedness. Trouble is, Ryan’s character starts off merely cold and unlikeable, then quickly turns downright psychopathic. Confronted with her husband’s request for a divorce, she responds by knocking him unconscious, duct-taping him to a toilet, and refusing to let him go until he admits he still loves her. Ryan even goes so far as to explicitly mention that she’s relying on Stockholm syndrome to win Hutton over. Failing that, she’ll have to fall back on forcing him to look at old photos of the way things used to be and ladling on the guilt, even as she freely admits that her own desire to hang onto him has less to do with love than her refusal to accept being lonely. Eventually, her actions put herself and her husband in extreme danger: A burglar breaks into their home, savagely beats Hutton, and repeatedly threatens to rape Ryan, all of which terrifies Hutton into taking her back. If the gender roles were reversed, that scenario would verge uncomfortably close to torture-porn. And the last-minute revelation that [spoiler alert!] Ryan likely planned the break-in all along only confirms she’s manipulative to a chillingly Machiavellian degree.
3. Jada Pinkett, Woo (1998)
The “straitlaced guy has his world turned upside down by one crazy night with an extroverted woman” scenario (as seen in Something Wild, Blind Date, etc.) is a common dude fantasy, but the fantasy requires that said extrovert has something going on besides the craziness—you know, to make up for all the alcoholism and psycho ex-boyfriends. But in Woo, behind Jada Pinkett’s revealing, Tex Avery-worthy outfits and attention-craving manic-depressive fits beats the heart of a stone-cold bitch. Naturally, Woo attempts to paint her selfish behavior as empowered—she can insult her meek, hesitant blind date (Tommy Davidson) because she’s all that, you see, and if she gets both of them thrown out of a restaurant by causing thousands of dollars worth of damage, all because she doesn’t like her table, well, that’s just the rollercoaster experience of being with a woman who speaks her mind! But her free spirit isn’t grounded in some rejection of societal conformity; she’s just a spoiled brat who’s used to men falling all over themselves to do her bidding. And still, we’re asked to care that she has yet to find the poor, unsuspecting man of her dreams. When Woo’s ex-boyfriend assaults Davidson in a nightclub, and he then emerges to find his car has been stolen, Pinkett doubles over with laughter, prompting Davidson to yell, “Maybe we could be having a good time, if you could control your psychotic mood swings!” Maybe, but why bother? There are plenty of other fish in the proverbial sea, and some of them are psycho in a fun way.
4. Jesse Bradford, I Hope They Serve Beer In Hell (2009)
Who would have thought that the Tucker Max movie would turn out to be such a conventional romantic comedy? In spite of the shit-spraying, midget-fucking antics that Max’s onscreen avatar gets up to, I Hope They Serve Beer In Hell is more dully predictable romance than sex farce. Most of its action focuses on one of Max’s buddies running around getting into antic trouble before his wedding, while the other, jilted misogynist Jesse Bradford, meets and is redeemed by a brilliant stripper with a heart of gold, a cute kid, and killer videogame skills. From the start, this total stranger is oddly eager to take Bradford into her home and help him deal with his vast emotional issues and rediscover love. Problem is, he’s never a remotely appealing character, let alone someone who seems interested in or worthy of redemption. This is a guy who approaches a woman at a bar, then—when she unwittingly and without malice does something that reminds him of his cheating ex—snaps “Get away from me, or I’m going to carve another fuckhole in your torso.” He’s a bristling ball of toxic quips and unsettling rants. He even comes along on his best friend’s bachelor-party road trip just to sit sullenly and snarl invective at the sluts, cunts, whores, and bitches of the world, who dare to share his air. The movie itself doesn’t have a much better attitude toward women, given that it so readily supplies him with a beautiful woman who has nothing better to do than drop everything and devote herself to absorbing all his bile.
5. Meg Ryan, Sleepless In Seattle (1993)
Romantic comedies often depend on telling audiences what they wish was true. Case in point: in Sleepless In Seattle, the seemingly happy engaged Meg Ryan hears Tom Hanks talking on the radio, falls in love with his voice, and spends the rest of the movie re-arranging her life to find him. In the real world, these would be the mentally unbalanced actions of a disturbed, desperate person, a quixotic quest for a relationship that couldn’t possibly live up to expectations. While Seattle pays some lip service to Ryan’s strange behavior, she’s ultimately rewarded for her “courage” with the most ideal meet-cute imaginable. Ryan’s delusions already indicate a person who could use some serious psychotherapy, but to make matters worse, she breaks the heart of her fiancée, a boring-but-nice Bill Pullman. There’s nothing wrong with ending an unhappy or unfulfilling relationship, but that Ryan was willing to let it go this far—and that she covers her escape under a quest for some illusory romantic ideal—means she’s destructive to others as well as naïve, short-sighted, and selfish. Hanks would be better off losing her number, although it’s doubtful that’d stop her for long.
6. Jack Nicholson, As Good As It Gets (1997)
“Why can’t I just have a normal boyfriend?” Helen Hunt asks near the end of As Good As It Gets. The line is played largely for laughs, but it also serves as a helpful audience reminder that Jack Nicholson, the film’s misanthropic, bigoted, obsessive-compulsive leading man, is supposed to be falling in love. Nicholson plays a romance novelist who divides his time between washing his hands and figuring out the worst possible thing to say to anyone he comes in contact with. He’s a jerk—and for some reason, that makes him a suitable love interest for the decades-younger Helen Hunt. Nicholson is decently charming, and his character is clearly making steps toward self-improvement by the movie’s end, but “someone who’s slightly less of a creep than he used to be” isn’t really anyone’s idea of a dream match. As Good As It Gets works as a character comedy-drama, but the romantic tension between Hunt and Nicholson never gets past the dictated-by-script phase, partly because Nicholson looks like a human-Sleestak hybrid, and partly because his newfound decency doesn’t make up for a life’s worth of vicious hostility.
7. Nia Vardalos, I Hate Valentine’s Day (2009)
The public embraced Nia Vardalos as a gawky ugly ducking among a flock of romantic-comedy swans in My Big Fat Greek Wedding, but 2009’s bizarrely misguided I Hate Valentine’s Day—which Vardalos not so coincidentally also wrote and directed—narcissistically casts her as a romance-crazed yet commitment-shy lunatic so irresistible that men are willing to submit to a stringent series of ground rules just to be able to spend five magical dates with her. (She has the protocol for each night mapped out as meticulously as a military campaign.) That might make sense if Scarlett Johansson were the one laying down the law for prospective suitors, instead of a mildly attractive, crazy-eyed 45-year-old. Instead, Valentine’s Day plays like a deranged vanity project, one deluded middle-aged woman’s heavy-breathing valentine to her inflated sense of her attractiveness.
8. Jennifer Garner, The Invention Of Lying (2009)
Jennifer Garner spends so much time obsessing about passing down genes for a litter of thin, athletic, non-pug-nosed supermen in Ricky Gervais’ The Invention Of Lying that audiences could be forgiven for mistaking her for the head of the Eugenics Society. Granted, the film takes place in an alternate universe where everyone blurts out the first thing that comes to mind and lying is an utterly foreign concept, yet even in this harsh realm devoid of white lies and pleasant evasions, the blunt, cruel Garner stands out for being egregiously superficial and obsessed with appearances. Even Gervais’ self-deprecating sad-sack deserves much better.
9. Aaron Stanford, Tadpole (2002)
In the dreadful romantic comedy Tadpole, Aaron Stanford plays a foppish 15-year-old dandy whose penchant for quoting Voltaire renders him irresistible to sexy women his own age. Ah, but Stanford’s pretentious, self-aggrandizing boob thinks he’s on a higher evolutionary plane than everyone else in his age group and species, so he pines for his stepmother, the only woman capable of appreciating the wit of his various bon mots. In reality, a precious poindexter like Stanford deserves a lifetime of swirlies and after-school beatdowns, not true love or the older woman of his dreams.
10. Amy Adams, Leap Year (2010)
In Leap Year, Amy Adams plays a depressingly ubiquitous romantic-comedy fixture: a seemingly sane, attractive, reasonable young woman whose life revolves around getting her jerky boyfriend to marry her. So she seizes upon an obscure/bullshit Gaelic tradition that allows women to propose to their boyfriends on February 29, and she heads to Ireland to snag a doctor in her mantrap. Along the way, she falls in love with roughhewn local Matthew Goode, but only after treating him to such snide condescension, class-based contempt, and verbal abuse that his eventual attraction to her rings masochistic.
11. Jenny McCarthy, Dirty Love (2005)
It’s especially cruel to condemn Jenny McCarthy’s Dirty Love character to a life of lovelessness. She certainly gets abused enough to warrant some sort of reward, even though the nice guy who was by her side all along is played by perpetually sad-faced American Pie star Eddie Kaye Thomas. Specifically, McCarthy’s character slips and slides through what looks like a life-ending amount of discharged menstrual blood as she wanders the aisles of a supermarket in search of a tampon. Later, a Woody Allen-like director vomits on her breasts. And yet, for all the humiliations heaped upon her, McCarthy’s character is still unworthy of love, if only because love seems outside McCarthy’s emotional range, which here ranges from bubbly to weepy to stupefied without a tender shade between.
12. Tom Hanks, You’ve Got Mail (1998)
There’s no more likeable actor in show business than Tom Hanks, a genial everyman who was not just the right choice, but possibly the only choice to play the Jimmy Stewart role in Nora Ephron’s modernization of the 1940 classic Shop Around The Corner. And while it’s entirely possible to make it through You’ve Got Mail without feeling a ounce of ill will toward his character, that’s mainly due to Hanks’ relaxed charisma. But consider this: Hanks, as the scion of a Barnes & Noble-like chain of heartless mega-bookstores, essentially wins over Meg Ryan, the proprietor of a boutique children’s bookstore, by putting her out of business. He’s the friendly face of the McDonald’s-ization of our culture, and Ephron seems to encourage Ryan to put up a good fight before eventually yielding to the soulless comforts of a literary Big Mac. Needless to say, that isn’t so easy to swallow.
13. Gerard Butler, P.S. I Love You (2007)
There’s nothing sadder than the love of someone’s life dying young. It can take time for the aggrieved to mourn and move on, to say nothing of finding that special someone who can adequately fill the void. A word to the dead: Respect the process and try to keep your ghostly nose out of it. As Hilary Swank’s recently deceased husband in P.S. I Love You, Gerard Butler takes an active interest in helping his wife get over him, but his romantic gestures look a lot like posthumous stalking. Sending a series of letters from beyond the grave, Butler’s ghost skulks around her and dictates her every move, eventually leading her to fly off to his native Ireland. It’s only when Swank finds a sympathetic barkeep (Harry Connick, Jr.) that he takes the hint: Nobody wants dead people telling them what to do.
14. Josh Hartnett, 40 Days And 40 Nights (2002)
It’s hard out there for a handsome cad like Josh Hartnett: When every available woman within a half-block radius wants to fuck you, how do you have time for anything else? And to that “boo-hoo,” here’s a double “boo-hoo”: When Hartnett vows to give up sex (including self-gratification) for Lent, how is the poor guy going to go cold turkey for less than a month and a half? Such is the gimmicky premise of 40 Days And 40 Nights, which banks on the audience feeling sorry for a stud-muffin who temporarily gives up a few weeks of the gratification he can get any time he pleases. Sorry, no dice.
15-16. Zach Braff and Natalie Portman, Garden State (2004)
The myth of the Manic Pixie Dream Girl was pushed to its most egregious extreme in Garden State, where beautiful Natalie Portman “redeems” a self-pitying, thoroughly unlikeable wimp (Zach Braff) by inexplicably falling in love with him, in spite of his rancid self-absorption and unseemly level of pussitude. In fact, she enables his bullshit, taking out a bottle to preserve his single, precious tear when he finally works up the nerve to cry over paralyzing his mother back when he was a kid. What makes the central relationship in Garden State even more unbearable (though, to the film’s credit, oddly realistic) is that Portman—a childish hipster doofus who mistakes goofy noises and arm-flailing for iconoclastic acts of individuality—is equally unworthy of love. So perhaps it’s best that they end up together rather than poisoning other, more decent people.
17. Sarah Jessica Parker, Failure To Launch (2006)
If anyone, real or fictional, deserves to spend a lifetime in a morass of lovelessness, surely it’s Sarah Jessica Parker in the thunderously stupid Failure To Launch. SJP plays Paula, a woman hired by gutless cowards to seduce their grown-up children living at home and convince them to leave the house. There’s a word for women that go on dates with men for money—actually, there are dozens of words, but we’ll stick with “prostitute”—but Parker gets extra asshole points for maliciously conniving to make poor, sweet (and surprisingly shirt-clad) Matthew McConaughey fall in love with her just so Terry Bradshaw and Kathy Bates can have uninterrupted, disgusting old-people sex. In accordance with the dum-dum rom-com handbook, Parker ends up “really” falling for McConaughey, who ultimately accepts her endearingly black-hearted, sociopathic ways. The scene where Parker then cuts open his neck and drinks the blood is apparently being saved for Failure To Launch 2.
18. Drew Barrymore, Never Been Kissed (1999)
It’s deeply unsettling to imagine the stories Never Been Kissed protagonists Josie (Drew Barrymore) and Sam (Michael Vartan) might someday tell their theoretical children about how they first met. Josie, a barely restrained psychopath who behaves like a mental patient, spends all her time alone stitching pillows and has lengthy conversations with turtles. Then she’s assigned to go undercover at a local high school. While there, she and English teacher Sam strike up an obvious flirtation, although he believes her to be 17 and she, actually 25, is also flirting with a teenage boy. When Josie’s deception is revealed, does Sam head for the hills? Of course not. The two get together, even though the entire pretense of their relationship is based on a potentially criminal lie.
19. Winona Ryder, Mr. Deeds (2002)
If trust is one of the keystones of a successful romantic relationship, then the romance between Mr. Deeds’ titular backwater rube and the big-city reporter who preys on his quaint (though insanely reductive) fantasy of rescuing a damsel in distress should fall apart somewhere in the first act. But backwater rubes being backwater rubes, newly minted billionaire Adam Sandler doesn’t realize Winona Ryder is only posing as an Iowan school nurse until he catches her unauthorized televised exposé of him—mere moments before she can come clean in person. (Of course, she only decides to come clean after failing to prevent her bosses from editing one story to make Sandler look like he killed several cats he actually saved from an apartment fire.) Were Mr. Deeds not a 21st-century update of a Frank Capra film, Sandler would live out the rest of his days as the crestfallen owner of a New Hampshire pizzeria, but the spirit of Capra-esque sentimentality allows Ryder to win back Sandler’s trust with a quick apology and one last act of muckraking—which saves the company Sandler wrongfully inherited, but still isn’t the change of heart the film makes it out to be.
20-21. Katherine Heigl and Gerard Butler, The Ugly Truth (2009)
For all who think modern romantic comedies are harmless, consider the plight of Katherine Heigl and Gerard Butler in The Ugly Truth, each playing characters who seem to be patterning their lives after what they’ve seen in rom-coms. She’s a busy morning-show producer who subjects all her romantic prospects to a checklist of what she’s looking for in a man; he’s a self-help guru who thinks all men are commitment-phobic animals who can only be caged by women willing to forgo their individual desires. The Ugly Truth is ostensibly about how happy Heigl and Butler would be if they just lightened up a little, but the movie doesn’t exactly set out to prove that either of them are wrong per se. All the women in the movie are hopelessly fussy, and all the men are sex maniacs. No one talks about their jobs, their faith, their political convictions, their favorite TV shows, their college days, their friends, the funny thing that happened to them at the supermarket… none of the things that make people interesting to be around. They’re too busy trying to trick each other into wearing vibrating panties.
22-23. Kate Hudson and Matthew McConaughey, How To Lose A Guy In 10 Days (2003)
Here’s a movie where the premise is so odious that any other irritations the characters might have just become more moss picked up by a giant, rolling ball of shit. How To Lose A Guy In 10 Days speaks to Hollywood’s inherent cynicism about love, the idea that anything can be overcome if you’re just hot enough. The very foundation of the “lasting relationship” Kate Hudson and Matthew McConaughey build in this film is riddled with cracks that are unlikely to be patched over by the two’s inherent physical attractiveness. Because each is treating the other as a pawn in an elaborate game, they’re effectively falling in love with fictional versions of each other, and becoming fictional versions of themselves to seduce each other. The worst thing about How To Lose A Guy is how easily it could be turned into a subplot in a 1970s paranoid-conspiracy thriller. (“My God. Even my girlfriend is in on it!”)
24. Woody Allen in anything
Chuck Klosterman once observed that guys who look and act like him would never get laid if it weren’t for Woody Allen. And it’s true—nobody is more responsible for turning neurotic, paternalistic, essentially self-centered men into supposedly smart, sensitive, even sexy objects of affection for women foolish enough to accept personality traits that would (rightly) seem obnoxious coming from much better-looking guys. At least Allen, of all people, seems to recognize how wrong this is, since guys like Alvy Singer and Isaac Davis always seem to end up alone at the end of movies like Annie Hall and Manhattan. And yet somehow before that, the Woodman always gets to canoodle with younger knockouts like Diane Keaton and Mariel Hemingway for 90 minutes.