In 2005, writer-director Michael Showalter (who recently directed the Oscar-nominated The Big Sick) hit upon a clever idea for an anti-romantic comedy. He would play Elliot, an ineffectual accountant and all-around pushover who’s engaged to the beautiful Caroline (Elizabeth Banks). But because it was a movie, we would know what was going to happen to Elliot before he did: Basically, she would dump his nice-guy ass for her bad-boy high school boyfriend Bradley (Justin Theroux). The subsequent film, The Baxter, put a name to the type of character who never ends up with the girl at the end of the rom-com: A “baxter” is the other guy, the loser, the dude who the audience is not rooting for.
We’re about ready for another Valentine’s Day, which means we’re going to see plenty of lists that celebrate the best romantic comedies of all time. But instead, I decided to pay homage to some of the most infamous “other guys” in cinematic history. These are the men who don’t land the leading lady — he’s the guy she rejects for her true love. The 10 examples below of rom-com failure run the gamut. Some of these “other guys” are jerks who deserved to be kicked to the curb. Some of them are wimps we feel bad for (a la Elliot). And a few were wronged by the movies they were in — they should have gotten the happy ending, not the other dude.
But then again, who ever said love was fair?
Pretty in Pink (1986)
The Other Guy: Duckie (played by Jon Cryer)
The Situation: Andie (Molly Ringwald) is a high-school misfit who catches the eye of a rich, handsome classmate named Blane (Andrew McCarthy), and romantic sparks ensue. None of this pleases Andie’s loyal pal Duckie, though, who’s been put in the friend zone, even though he pines for her.
How Bad Should We Feel for the Other Guy? Cryer is still not over the fact that director Howard Deutch didn’t stick with screenwriter John Hughes’ original ending, which had Duckie and Andie falling in love. “I think it’s a historic wrong that will never be completely righted,” the actor said, jokingly, in 2006, later adding, “I was disappointed. You sorta go, ‘Oh, guess I’m not the leading man.’ But I think it was kind of appropriate. Duckie always thought he was the leading man, and that was his fatal flaw.”
Still, for a lot of guys who were nice-guy nerds growing up in the 1980s, Pretty in Pink signaled that the Milhouses of the world were going to have a tough time dating.
Sleepless in Seattle (1993)
The Other Guy: Walter (played by Bill Pullman)
The Situation: The amiable, loyal Walter is engaged to Annie (Meg Ryan), a reporter who becomes drawn to a widowed single father named Sam (Tom Hanks). After hearing Sam on a radio call-in show talking about how much he still misses his dead wife, Annie begins to realize that maybe her life with Walter isn’t that romantic or fulfilling. Her disenchantment comes to a head when she breaks up with him during Valentine’s Day dinner, ceremoniously handing him back his engagement ring.
How Bad Should We Feel for the Other Guy? Honestly, really, really badly. Walter might be the quintessential rom-com sad-sack. There’s nothing inherently wrong with the guy — he’s not a bad person, but he’s cursed not to be as charming as Tom Hanks. (To stack the deck a little, director Nora Ephron also gave Walter bad allergies as a sign that he’s a bit of a loser.)
Years later, fans of Sleepless in Seattle still wrestle with how Walter is treated by Annie. Writing in Vulture in 2018, Jen Chaney imagined how this 1990s classic would feel from his perspective, marveling at how well he handles getting dumped. “He is calm,” she writes. “He is rational. He is more mature than anyone should ever be expected to have to be. … He says he’s okay, but inside Walter has got to be livid and heartbroken. Annie may have fallen for a man who lost his wife, but she’s taken the promise of a wife away from Walter in the process and she doesn’t even realize it. She’s made Walter a pseudo-widower before he even had the chance to be wed.”
Walter is the embodiment of the worst fears nice guys have about themselves: If they’re not careful, a movie star will come along and steal their woman.
Reality Bites (1994)
The Other Guy: Michael (played by Ben Stiller)
The Situation: Lelaina (Winona Ryder) is an idealistic aspiring documentarian who meets-cute with Michael, a materialistic cable-TV executive. She’s attracted to his success and ambition, but she also feels drawn to her old pal Troy (Ethan Hawke), a slacker musician who rejects Michael’s sellout mentality. Ultimately, she chooses idealism over material success.
How Bad Should We Feel for the Other Guy? At the time of its release, Reality Bites felt like the definitive Gen-X portrait, forcing a young woman to decide between falling for a soulless corporate drone and, like, a real artist, man. Even back then, though, it seemed that Lelaina made the wrong choice. Sure, Troy is a decent guy, but he’s sorta going nowhere with his life. And Michael is actually a pretty nuanced, sweet person… until the movie conveniently turns him into a jerk after he recuts her documentary to make it flashier. But this was very much how the 1990s were: Anybody associated with “the man” was inherently evil. For what it’s worth, Michael has probably had a perfectly fine life without Lelaina — and there’s no way she and Troy are still together.
While You Were Sleeping (1995)
The Other Guy: Peter (played by Peter Gallagher)
The Situation: Peter is a good-looking dude who’s the secret crush of Lucy (Sandra Bullock), who collects the fares for Chicago’s transit commuters. Lucy never thinks she could land a guy like him, but after she rescues him from a mugging, which puts him in a coma and incorrectly gives his family the impression that they’re engaged, she decides to play along — only to fall in love with his kindly brother Jack (Bill Pullman).
How Bad Should We Feel for the Other Guy? Eh, Peter will be okay. What was funny about While You Were Sleeping was that it allowed Pullman, post-Sleepless in Seattle, to finally end up with the girl. As for Peter, it’s not like there’s any real heartbreak. He never even knew Lucy, and he looks like Peter Gallagher, so he’s going to be just fine.
The Wedding Singer (1998)
The Other Guy: Glenn (played by Matthew Glave)
The Situation: Adam Sandler plays Robbie, a luckless wedding singer in the mid-1980s who’s hired by Julia (Drew Barrymore) to perform at her and Glenn’s wedding. But the more that Robbie and Julia spend time together, it becomes obvious there’s a love connection brewing.
How Bad Should We Feel for the Other Guy? Simply because of the fact that he’s named Glenn — and he’s a yuppie — we’re free to assume that he’s a terrible person. And he is, constantly cheating on her and generally acting like a heel. Some romantic triangles are meant to leave us in suspense, but early on in The Wedding Singer, it’s clear where our loyalties should lie. This movie marked Sandler’s gradual maturation: Sure, the comedic superstar still emphasized sophomoric humor, but Robbie was a good, sweet guy. So it was a delight to watch him steal Julia away from that creep Glenn.
There’s Something About Mary (1998)
The Other Guy: Pat (played by Matt Dillon)
The Situation: Ted (Ben Stiller) has loved Mary (Cameron Diaz) since they were kids. (Don’t bring up prom.) He decides to hire a sketchy private investigator, Pat, to see whatever became of her — but during his sleuthing, Pat decides he wants Mary all for himself.
How Bad Should We Feel for the Other Guy? Pat is the movie’s clear villain who schemes to keep Ted and Mary apart. (His moustache is a dead giveaway that the character is a primo douche.) Nobody feels bad for Pat. Ironically, even though Pat doesn’t end up with Mary, Dillon did land his costar in real life: He and Diaz dated for several years before There’s Something About Mary, breaking up soon after. “I was dissatisfied with where I was as a man, with my relationships, with my career,” he would say later. “Like a lot of guys, I was driven by my work. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn’t been in any deep emotional relationships.”
Bridget Jones’s Diary (2001)
The Other Guy: Daniel (played by Hugh Grant)
The Situation: The lovable but massively insecure Bridget Jones (Renée Zellweger) is having a fling with her arrogant, dreamy boss Daniel, but is she destined to fall for Mark (Colin Firth), who’s uptight but may secretly be a sensitive, soulful guy under his stuffy, judgmental veneer?
How Bad Should We Feel for the Other Guy? Based on the popular Helen Fielding book (which was a modern twist on Pride and Prejudice), Bridget Jones’s Diary presents a familiar “bad boy vs. nice guy” rom-com scenario, in which the main character learns that the hot-but-emotionally-unavailable man is ultimately not worth it — better, instead, to go with the slightly more unassuming gent who will treat you well. (If he looks like Firth, even more reason to go for it.)
As for the Daniels of the world, well, Grant had some thoughts about the character, whom he reprised in 2004’s Bridget Jones: The Edge of Reason. “I don’t know that he’s evil,” Grant once said. “I think he just had it too easy, that was always my theory about Daniel. For too long, I think he was the clever, attractive and quite funny one in school, the university and the early years of his career. You know, it was very easy for him to pick up girls, and he just enjoyed himself. And now, the honeymoon is starting to get a little sour.”
Wedding Crashers (2005)
The Other Guy: Sack (played by Bradley Cooper)
The Situation: A spoiled, mean frat-bro, Sack is dating the lovely Claire (Rachel McAdams), who as a bridesmaid at her sister’s wedding meets John (Owen Wilson), a goofy divorce lawyer who crashes weddings with his best friend and fellow attorney (Vince Vaughn). Sack is immediately suspicious of John, who can’t understand why she’s going out with him.
How Bad Should We Feel for the Other Guy? Not one bit. Wedding Crashers is a classic example of how to create a romantic triangle in which you’re really, really rooting for the current boyfriend to lose out to the new guy. (Of course, what Claire saw in Sack in the first place is unfathomable.) Not only is Sack a jerk, he’s also a serial womanizer, something Claire doesn’t realize.
The role did, however, help launch Cooper’s film career — he was a vibrant boo-hiss villain. The film’s director, David Dobkin, told me in 2017, “My saying is that you never, ever hire someone in the room — you have to always go back and watch the tape. Bradley Cooper is the only person who was an exception. I couldn’t find anyone [to play Sack], and then he came in the room and he was amazing. He was like a thoroughbred. I remember going up to him and saying, ‘Dude, you’re awesome! You got the part!’”
The Other Guy: Prince Edward (played by James Marsden)
The Situation: Giselle (Amy Adams) lives in a literal magic kingdom, but when she’s transported into the real world, she discovers that life is nothing like a Disney animated movie. She’s followed by Edward, the prototypical fairytale prince, into modern-day New York City, where she unexpectedly falls for the hard-nosed divorce attorney (and single father) Robert (Patrick Dempsey).
How Bad Should We Feel for the Other Guy? Enchanted is an underrated Disney romantic comedy that makes fun of the studio’s princess obsession and enchanted-forest aesthetic. As a result, it’s clear from the beginning that Edward is meant to be an endearing cliché and not the man Giselle will end up with. Marsden has a ball playing this empty-headed, duly valiant, constantly-singing prince — he’s as dull and handsome as any of the guys who sweep Sleeping Beauty or Snow White off their feet. Don’t feel bad for Edward, though: He winds up with Nancy (Idina Menzel), who’s actually engaged to Robert but realizes she’d be better off with a real prince.
Juliet, Naked (2018)
The Other Guy: Duncan (played by Chris O’Dowd)
The Situation: Annie (Rose Byrne) is in a long-term relationship with Duncan, who is obsessed with a forgotten cult musician, Tucker (Ethan Hawke), who hasn’t recorded in years and has become a recluse. Confused by her boyfriend’s fascination with this songwriter, Annie writes a negative review of some of his work online, inspiring an email response from Tucker — and a love affair.
How Bad Should We Feel for the Other Guy? Juliet, Naked is based on a Nick Hornby novel, and like the English author’s High Fidelity, the movie is populated by manchildren who are infatuated with their record collections. As with Reality Bites, Hawke plays the female character’s ideal man, but at least in this film it sorta makes sense. Duncan is the classic example of the kind of pop-culture guy who tries to turn his girlfriend onto all of his favorites, even if she couldn’t care less. Sometimes, you feel bad for the “other guy” in romantic comedies. With Juliet, Naked, you hope getting dumped will help Duncan grow up.