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Sign in to your Collider account Summary Generate a summary of this story follow Follow followed Followed Like Like Thread Log in Here is a fact-based summary of the story contents: Try something different: Show me the facts Explain it like I’m 5 Give me a lighthearted recapWhen Harry Met Sally premiered in 1989 and practically redefined what romantic comedies could look like. The film, directed by Rob Reiner and written by Nora Ephron, remains the blueprint for the genre, but at the same time, very few films have come close to recreating its impact. The story follows Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) over twelve years and attempts to answer the question of whether men and women can truly just be friends.
What makes the romcom so memorable is how realistic and honest it was in its portrayal of love. Over the years, many films have tried to capture the effortless charm of the classic. If I'm being honest, though, most of them have completely failed. Here are 10 of the worst movies that tried to be When Harry Met Sally because they just didn’t understand what made the original work in the first place.
10 ‘The Ugly Truth’ (2009)
Katherine Heigl and Gerard Butler dancing in The Ugly TruthImage via Sony Pictures
Katherine Heigl is a great performer, but even she couldn’t save The Ugly Truth from feeling like a clichéd mess of gender stereotypes. The film promised an entertaining gender-war plot with Heigl as TV producer Abby, who believes in love with all her heart. On the other hand, Gerard Butler’s Mike is the exact opposite, who leans a little too heavily into the unapologetic misogynist archetype. The film had the potential to put a modern spin on the opposites-attract trope, but unfortunately, the writing just fell flat. One of the biggest issues with The Ugly Truth is that the film cuts out practically every scene that could have made its central relationship interesting.
The original script was meant to dive deep into Abby’s insecurities and why she keeps sabotaging her relationships, while giving Mike’s character emotional depth, too. However, several rewrites led to the film losing all this edge and sticking to one-dimensional portrayals of Abby as nothing more than an uptight woman. Even the comedic bits of the film fail to work because after spending about 90 minutes mocking the very idea of romance, the film suddenly ends with a grand rom-com gesture that magically makes all the fundamental differences between the leads disappear. There’s no denying that The Ugly Truth is entertaining if you’re looking for a mindless watch, but the film definitely tried to capture the magic of When Harry Met Sally without focusing on what made the classic work.
9 ‘My Best Friend’s Girl’ (2008)
Kate Hudson smiling at Dane Cook in My Best Friend's Girl. Image via Lionsgate
After My Best Friend’s Wedding (1997), there was My Best Friend’s Girl, but that’s where the similarities end. In fact, My Best Friend’s Girl tries to channel the sharp-edged honesty that When Harry Met Sally used to critique the very idea of dating, but fails horribly at it. The Howard Deutch rom-com follows Dane Cook as Tank, whose side hustle is taking women on unimaginably bad dates so they will go running back to their exes. Now, the film could have run with this premise and turned the narrative into a sharp commentary on the absurd expectations that come with modern relationships.
However, My Best Friend’s Girl never fully explores that and turns Tank into a juvenile character who only exists for shock value. Kate Hudson’s Alexis is the girl both Tank and his roommate Dustin (Jason Biggs) are trying to woo. For starters, Alexis isn’t actually dating any of the guys, so the title of the film is inaccurate. That could have been overlooked if Alexis’s character hadn’t been reduced to a manic pixie dream girl with no personality outside of drinking, hooking up, and reacting to whatever shenanigans Tank would be up to. The movie just feels mean-spirited, so when Tank suddenly goes from a jerk to a total loverboy, the act just isn’t believable. Add all the crude jokes and tonal shifts between emotional sincerity and vulgarity to the mix, and this rom-com is just not worth suffering through.
8 ‘Someone Like You’ (2001)
Image via 20th Century Fox
Someone Like You premiered 12 years after When Harry Met Sally and tried to put a spin on the classic rom-com. The film stars Ashley Judd as Jane Goodale, a production assistant who thinks she has found her soulmate in Ray (Greg Kinnear), only to be dumped by him. That sends her into a weird spiral about a theory of how men date based on bovine mating habits. As crazy as it sounds, the film doesn’t treat the whole thing as satire, and that’s the worst part. Someone Like You leans into this cow metaphor so hard that Jane’s actual character arc takes a backseat. The film turns into this faux social commentary about gender that just lacks substance and borders on the edge of sexism.
Jane often reduces men to livestock and compares herself to a used-up old cow, and you never really know if she’s joking or being serious. Don’t get me wrong, Judd does everything she can with her badly-written role, and Hugh Jackman is definitely easy on the eyes as her coworker and roommate, Eddie. However, their romantic arc doesn’t start until halfway through the story, and this sudden shift just feels rushed and half-baked. Someone Like You is the perfect example of a film that pretended to be way more intellectual than it really was, and in doing so, it proved to be one of the most forgettable releases of 2001.
7 ‘Along Came Polly’ (2004)
Jennifer Aniston and Ben Stiller in Along Came Polly dancing together.Image via Universal Studios
Along Came Polly had everything working for it on paper. The John Hamburg film followed Ben Stiller as Reuben Feffer, a risk analyst whose life falls apart when he catches his wife, played by Debra Messing, cheating on their honeymoon. This is already a great setup for a story about self-discovery, and it takes a welcome turn when Reuben connects with his former middle-school classmate Polly Prince (Jennifer Aniston). Polly is the exact opposite of Reuben with her spontaneity. Right off the bat, the audience can tell that she is designed to bring him out of his shell and show him that there is more to life than spreadsheets.
Unfortunately, the film reduces Polly to just that without even trying to add any kind of depth to her character. Aniston is effortlessly likable and funny, but that has everything to do with the actress and nothing to do with the writing. It’s almost like her only purpose is to fix Reuben, and if this was Hamburg’s way of recreating Harry and Sally’s dynamic, he failed pretty badly. Every milestone in Reuben and Polly’s story checks a rom-com box without ever feeling real. The supporting characters in Along Came Polly, including Philip Seymour Hoffman’s Sandy and Hank Azaria’s Claude, feel more complex than the leads, and that tells you all you need to know about the film. Aniston and Stiller do have chemistry that would have worked effortlessly in any other rom-com, but sadly, this story doesn’t give their connection any depth.
6 ‘Little Black Book’ (2004)
Image via Sony Pictures Releasing
Little Black Book attempts to tell a story about how modern dating anxieties can manifest in questionable behaviors. However, instead of exploring that idea with maturity, it turns the central character, played by Brittany Murphy, into a total joke. The film follows the actress as associate producer Stacy Holt, who decides to dig through her boyfriend Derek’s (Ron Livingston) past. Stacy’s actions make her look like a total stalker as she goes through Derek’s phone, calls his exes under pretenses, and infiltrates their lives just to understand why he is so scared of committing to her. If the film is meant to provide commentary on how the idea of modern dating pits women against each other, it completely fails in doing so because of how jealous Stacy comes across.
What’s shocking is that Murphy is genuinely brilliant in her role and brings a neurotic charm to her character. However, that isn’t enough to make her a likable character as she violates every boundary people set against her. By the end, you’re left wondering if the film has manipulated you to root for someone who would have definitely been sent to jail for all the laws she broke while trying to snoop on her boyfriend. Not just that, but Little Black Book also keeps shifting genres and goes from a light rom-com to a cynical workplace satire in the blink of an eye. What you get is a movie with little to no romance, mediocre jokes, and characters you can’t bring yourself to root for.
5 ‘Love Happens’ (2009)
Image via Universal Pictures
Love Happens was marketed as a tender romantic story about two lonely people finding solace in each other. The premise follows self-help author Burke Ryan (Aaron Eckhart), who helps people overcome loss while he still grieves his wife’s death. Jennifer Aniston plays Eloise Chandler, a florist who can’t help but date the wrong men. When Burke and Eloise meet, the film sets the stage for a relationship that is meant to progress naturally as the two open themselves up to love and vulnerability. However, the film does a massive disservice to Aniston and gives her character no growth or personality at all.
Love Happens sets out to explore emotional honesty in relationships like When Harry Met Sally did, but the script forgets to focus on actually giving us a dynamic worth rooting for. Sure, the story needs to spend time with Burke and his grief seminars, but it does so at the expense of Eloise’s emotional arc. As a result, the central characters never feel like a believable couple because we only get to see one side of the story. Aniston and Eckhart share great chemistry, but it never feels like they are falling madly in love.
4 ‘Life as We Know It’ (2010)
Josh Duhamel in Life As We Know ItImage via Warner Bros.
Life as We Know It follows bakery owner Holly (Heigl) and laid-back sports director Messer (Josh Duhamel), who go on the worst blind date ever and walk out absolutely despising each other. However, when their best friends suddenly die in a car crash, Holly and Messer find out that they have been named joint guardians of their baby Sophie. The setup is brilliant and leaves a lot of potential for the central characters to grow up, grieve the loss of their friends, take on this major responsibility, and fall in love in the process. However, the film does none of that and leans heavily on sitcom-style gags that disguise mindless bickering as romantic tension.
The script is so formulaic that the characters’ shift from being reluctant co-parents to genuine partners just doesn’t feel as gratifying as it should. The film’s constantly shifting tone is also bound to be a dealbreaker for avid romcom fans because it completely fails to reconcile all the themes that unfold with the narrative. Life as We Know It rushes past the hard parts, such as the characters’ self-doubt, commitment issues, and creates conflict around shallow misunderstandings that could have been solved with a text message. Heigl and Duhamel’s acting is the only thing that saves this trainwreck of a rom-com.
3 ‘Alex & Emma’ (2003)
Image via Warner Bros. Pictures
Reiner, the director of When Harry Met Sally, helmed Alex & Emma, so naturally, fans had high expectations of the film. The rom-com starring Luke Wilson and Kate Hudson starts with a lot of promise. The story follows Wilson as Alex, a novelist who has 30 days to finish his book or risk being killed by Cuban loan sharks. That’s where things start feeling a little cartoonish because there was absolutely no need for the film to rely on a borderline deadly countdown to create tension. Hudson plays Emma, a stenographer Alex hires to help him dictate his novel. Instead of using that to build their romance, the film keeps cutting to scenes of the book they are writing. Here, Hudson appears as different nannies with all kinds of accents, while Wilson plays a fictional version of Alex, who falls for the last nanny he meets.
The idea could have been unique and fun, but this constant back-and-forth takes away from the actual story. Reiner, who excelled at letting romance unfold through simple conversations and small gestures in When Harry Met Sally, tries to do something way more ambitious with Alex & Emma, but the concept falls flat. The film feels gimmicky and relies on its fictional scenes to drive the real-world romance, and that never really comes together as effortlessly as intended. The conclusion feels predictable, and because we actually don’t spend any time getting to know these characters on a deeper level, it just doesn’t hit hard.
2 ‘The Switch’ (2010)
Jason Bateman and Jennifer Anniston holding arms in The SwitchPicture from Miramax Films
The Switch has to be one of the strangest rom-coms of the 2010s. The premise itself isn’t that wild. You have Aniston and Jason Bateman, who share wonderful chemistry on-screen. The film follows the Friends star as Kassie, a single woman in her late thirties who decides that she doesn’t want to wait for the perfect man to have a baby. Bateman plays Wally, her neurotic best friend who has been in love with her for years but never said anything. The plot thickens when Wally accidentally spills Kassie’s chosen donor’s (Patrick Wilson) sperm sample and replaces it with his own. Now, because Wally is completely drunk at the time, he doesn’t remember any of this until seven years later, when he meets Kassie and her son Sebastian (Thomas Robinson), who is a mirror image of himself.
Soon enough, Wally starts bonding with the boy and realizes that he is his child. He then has to come clean and tell Kassie about his mistake from all those years ago. The premise is strong and leaves a lot of room for a romance that the audience can actually root for, and Bateman does a great job of portraying Wally’s internal conflict as he reacts to the switch. However, what doesn’t come across so well is how long Kassie is kept in the dark. The film could have explored the natural progression of two friends falling for each other after realizing that they share a child. There is barely any time left for Aniston’s character to react to all this, though, because the film is rushing toward a happily-ever-after a few minutes after the big reveal. The Switch starts strong, but falters in its pacing, and that is the film’s biggest mistake.
1 ‘Laws of Attraction’ (2004)
Image via Mobius Pictures
Laws of Attraction had all the makings of a classic rom-com with Julianne Moore and Pierce Brosnan in the lead. The story follows Moore as Audrey, a New York divorce attorney whose life is planned down to every single minute. On the other hand, Brosnan as the disheveled lawyer Daniel Rafferty is her exact opposite. The setup mimics When Harry Met Sally’s battle-of-the-sexes trope as the two face off in a series of messy, high-profile celebrity divorces. However, their rivalry takes a turn when a case involving a rock star and his designer wife causes them to travel to Ireland. The work trip takes a turn when the two end up drinking together at a local festival and wake up the next morning accidentally married.
After the news leaks to the press in New York, the two decide to stay married and pretend to be a couple for the sake of their careers. As Audrey and Daniel start living together despite really not wanting to, they slowly begin to enjoy each other’s company. Laws of Attraction’s strongest element is the chemistry between its two leads, whose banter is the heart of the film. Unfortunately, though, the rom-com focuses more on situational chaos to push the couple together instead of letting their romance bloom through honest character growth. The film would have come close to capturing the magic of When Harry Met Sally if it weren’t for its screwball antics and endless clichés.
Laws of Attraction PG-13 Comedy Action Romance Thriller Release Date April 4, 2004 Runtime 90 minutes Director Peter HowittCast
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Pierce Brosnan
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Julianne Moore
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Michael Sheen
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Parker Posey
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