In spite of the fact that every film connoisseur doesn't always appreciate them, romantic comedies are a staple in the industry. Because it needs to feel organic and relatable, it's often said by various writers that it's harder to write, produce, and deliver a good romantic comedy. This makes the great ones that much more excellent because the care that's put into them centers around the characters and makes the stories believable. In addition, the genre is full of delicious tropes to explore, and one that's often utilized is the "bad boy/good girl." It's evolved throughout the years to take on a more nuanced approach, but the '90s and early 2000s were full of bad boys that almost every viewer swooned over.
There's also a nuanced definition as to what a bad boy is and what makes their eventual love story feel earned. That said, here are the seven best rom-com bad boys and where you can watch them on platforms such as Hulu, Prime Video, and more.
Patrick Verona - 10 Things I Hate About You (1999)
Inspired by Shakespeare's Taming of the Shrew, 10 Things I Hate About You is the ultimate rom-com featuring a swoonworthy bad boy. The late Heath Ledger delivers the type of unforgettable performance that ensures Patrick Verona is not only layered, but that every character detail about him feels realistic. A large part of the reason the trope feels too saccharine or hard to believe is that the writing leans too close into stereotypical archetypes, whereas 10 Things I Hate About You dives deeper into the character's psyche and explores all the questions that might arise from his decisions.
It also helps because Julia Stiles' Kat Stratford doesn't change who she is in order to appeal to Patrick. Grease (1978) is another film that explores this route, but over the years, it's become increasingly clear that Sandy's change in the end isn't true to her character, but rather services Danny Zuko's instead. Patrick Verona isn't the type of bad boy to want that, and it makes him that much more riveting as a character for fans of classic rom-coms.
Jacob Palmer - Crazy, Stupid, Love (2011)
Crazy, Stupid, Love is an underrated gem that pulls off multiple classic rom-com tropes, all while delivering one of the most unexpected plot twists in a comedy film. Ryan Gosling's Jacob Palmer isn't the traditional high school bad boy, but rather the player who refuses to settle down—the cocky, arrogant, and well-dressed, put-together, no-nonsense kind of man who doesn't want any personal interactions or to crack open his walls. When he's paired with Steve Carell's Cal Weaver to help him get back on his feet after his wife leaves him, things eventually change when Cal's daughter serendipitously crosses his path.
Jacob's transition from a man who's completely guarded to one who's willing to learn how to love works entirely because of Gosling's performance and because the movie spends a decent amount of time showing how he and Emma Stone's Hannah connect through honest conversations without expecting anything from each other. It's supposed to be a one-night stand, no strings attached, but Crazy, Stupid, Love shows how it can become something bigger when people are allowed to be their truest selves around another person. It's an absolute must-watch for a number of reasons.
Tyler Gage - Step Up (2006)
Diving back into the world of teenagers and way-too-much angst, Step Up centers around Channing Tatum's Tyler Gage and Jenna Dewan's Nora Clark after he pairs up with her during his community service punishment for vandalizing a performing arts school. On the surface, Step Up could've been a cliché, but as the first film in what becomes a popular franchise, the exploration of how hobbies can be healthy for distressed and broken teens is a solid theme to explore.
The rom-com's combination of classic ballet and hip-hop dance moves is one of the biggest appeals in its production, and simultaneously, how the film explores Tyler and Nora carefully falling for one another. Again, none of these narratives tries to change one person's character beyond who they themselves want to be, but rather in getting to know each other, both Tyler and Nora bring out the best in each other. All of this happens as he learns how to use his time and talents in a way to improve the type of future he never thought he'd be able to achieve.
Zack Siler - She’s All That (1999)
She's All That is a classic cliché on all fronts, and it doesn't exactly hold up to today's standards, but it still works when we examine the film's layers. One of the most important details to note is that high school kids ultimately don't know any better, and while no woman (or man) needs a makeover to be loved, there is some understanding of the trope when it's what they want. More than anything, Freddie Prince Jr.'s Zack Siler understands the errors of his ways, which makes the eventual happy ending with Rachael Leigh Cook's Laney Boggs feel earned.
Zack is the kind of bad boy whose decisions come from arrogance, and ultimately, his friends. His motives also tend to make sense, which then helps ensure that the audience understands him enough to care for his happy ending, too. What we get in the film works as an exploration of not-so-great tropes being handled with care, and that's exactly what makes She's All That a classic rewatch for romance fans to this day.
Nick Leister - My Fault: London (2025)
Inspired by the Spanish Culpa Mia trilogy, the British version, My Fault: London, follows a relatively similar narrative plot in exploring a forbidden romance. Matthew Broome's Nick Leister passes his time engaging in secret underground fights and racing illegally. When his equally rebellious new stepsister comes into the picture and has her own heartaches to deal with, the two of them eventually embark on a tumultuous secret relationship.
Interestingly, the rom-com (a bit more drama) does something riveting by making the two of them equal in different ways. She's not exactly the good girl next door who's about to inspire him to make better choices, but rather the time they spend together allows them the opportunities to open up in ways that give them the space to unload some of their burdens. As two people with issues surrounding their parents, Nick and Noah character journeys feel well-rounded and admirable. At the same time, the film is a whole lot of fun despite the drama with rom-com beats that provide plenty of entertainment for fans of the genre.
Flynn Rider - Tangled (2010)
As far as animated bad boys go, Disney has had its fair share of them, from Aladdin to Scar, Robin Hood, and even the suave Thomas O'Malley from The Aristocats (1970). But there's something especially enticing about Flynn Rider, or rather, Eugene Fitzherbert, and the love story that builds between him and Rapunzel in Tangled. Disney princes aren't always given the same type of riveting backstory that the princesses are, and that's also one of the distinguishing factors in Tangled that makes it such a fan favorite.
The romance isn't just about the prince rescuing the princess; it's also about two people learning how to dream together. Flynn Rider is everything Mother Gothel warns Rapunzel about. However, if she were raised in the kingdom by her own parents, then they'd likely have their hesitations, too. It's a classic, albeit silly, tale of misunderstandings and good motives going awry, and Tangled effectively manages to make Flynn Rider nuanced, endearing, and the type of unlikely hero whose old ways are a result of no one seeing him as well as Rapunzel can. Whether you like Disney’s other animated movies, or just need a new bad boy to root for, Tangled checks the boxes.
Joe Fox - You’ve Got Mail (1998)
Joe Fox isn't the traditional bad boy—at least not while he's on AOL Instant Messenger—but he represents a different kind of edge that adds nuance to the trope in rom-coms. He and his father's company are setting out to close small businesses, and while there may not be complete malice in the act, but rather a financial decision, there's a lot to explore about the world of capitalism and billionaires. In addition, while Tom Hanks is a general heartthrob, part of what makes You've Got Mail so deliciously angsty is how fiercely Meg Ryan's Kathleen Kelly loathes him in the beginning. And he knows exactly what he's doing by pushing all her buttons, especially when he learns who she is and crashes the date anyway.
Through Joe Fox, we get an interesting, everyday insight into what a "bad boy" actually encompasses. It's not always about rebellion that makes them hard to trust, but sometimes, it's deeper—it's questioning their morals and determining if they align with yours before marking on something permanent. Luckily for Kathleen, Joe Fox is her perfect equal, and the film continues to stand the test of time because of how it explores various tropes through organic depictions that ensure the character journeys are relatable and nuanced.
