The Bad Boy Trope, Explained

The Bad Boy. He’s the guy your mother warned you about. Our culture can’t get enough of Bad Boys like James Bond, James Dean, Marlon Brando, Han Solo, Tony Stark, Edward Cullen, Dylan McKay, Joker and Christian Grey. So why is our culture so obsessed with these dangerous guys?


The bad boy. It seems like he’s been around forever – in movies, books, TV, even music. He’s the guy who’s not so nice. But we’re supposed to obsess over him anyway, not despite his antisocial qualities, but because of them. Looking at the Bad Boy onscreen over the years, there are some key recurring qualities that define him:

  • He stands out from the crowd.

  • A bad boy acts like he doesn’t care about “normal” morals or values —he’s created to be the antithesis of the nice guy.

  • Of course, once we get to know him, we learn he does care about right and wrong—just on his own terms.

  • The bad boy is the strong, silent type, the human equivalent of a mystery waiting to be solved.

  • He’s stereotypically attractive — usually tall, dark, and handsome. To cite the old cliché, men want to be him, and women want to be with him. And that’s fitting because the Bad Boy is a cliché.

  • Most important of all, the Bad Boy seemingly has the potential to be redeemed by love, from a girl who cares enough to try and fix him.

While there are different types of Bad Boy, and those types have changed over time, popular culture has started to turn against this character type. Here’s our Take on the Bad Boy—what he represents, how he’s evolved onscreen, and why Bad Boys aren’t as bad as they once were.

A Brief History Of Bad Boys

Bad Boys, in their purest form, represent temptation—something that’s not good for you, but you want it anyway. As John Milton’s Satan says in “Paradise Lost,” “Better to reign in hell, than serve in heaven.” That original embodiment of bad is the archetype that defines the Bad Boy. Charismatic, arrogant, attractive—simultaneously alluring and dangerous. In the 1930s and ‘40s, bad boys were the men in gangster movies—James Cagney and Humphrey Bogart, playing outlaws, seducers, guys who broke laws and hearts at the same time. But these guys always got their comeuppance—the Hollywood studio system made sure characters who behaved like that got punished.

But by the ‘50s, as the cracks began to appear in Hollywood’s system of self-censorship, movies began to portray Bad Boys more as tragic figures than villains. They were still impossibly cool, but their bad behavior was usually a mask for some noble or misguided idealism. In other words, they were Bad, but with a hidden reserve of Good inside.

Jim Stark: “Please, lock me up. I’m gonna hit somebody, I’m gonna do something I don’t…” - Rebel Without A Cause

The new embodiments of this masculine Bad Boy image were Marlon Brando and James Dean, avatars of outlaw cool who behaved irresponsibly onscreen, but who also revealed fragile beating hearts beneath their tough exteriors. This change was symbolically depicted in their fashion choices, too. As Vanity Fair’s Laura Jacobs notes, both men wore white T-shirts, an item of clothing that had previously been considered an undershirt. This represented the way these Bad Boys were exposing the inner vulnerability that had historically been covered up. By the end of the decade, it was the wardrobe of choice for any Bad Boy onscreen, even the singing and dancing type.

By dying at the young age of 24, James Dean became the iconic figure of Bad Boy rebellion, so much so that, decades later, TV shows introducing Bad Boy characters were still imitating his style. Beverly Hills, 90210’s Dylan McKay was the classic James Dean Bad Boy, right down to his perfectly coiffed hair.

And on Gilmore Girls, the arrival of Milo Ventimiglia’s character Jess introduced a new generation of kids to the Dean-style Bad Boy. A rude outsider who always gets into trouble, Jess is standoffish, often cruel, and uninterested in proper social behavior. So, naturally, Rory has to fall for him.

Jess Mariano: “Think how dull your life would be without me.” - Gilmore Girls 2x19

But it wasn’t all James Dean knock-offs. There were other versions of the Bad Boy that entered the popular consciousness. The swinging ‘60s saw the ascendance of the Rat Pack—the suit-wearing band of entertainers led by Frank Sinatra, Sammy Davis Jr., and Dean Martin. They embodied a more adult version of the Bad Boy—the Bad Man, so to speak. And the movies they starred in usually emphasized that any attachment to a woman in their lives was destined to be short-lived—at least until the right one came along. This type of Bad Boy is more concerned with where the next party is than with any tortured idealism. His appeal is based in expensive style, cocky attitude, and the romanticism of “living for the moment” — and the idea that we could die at any time, so we better seize the day and live it up. A more recent version of this Bad Boy can be found in the 1996 movie Swingers—Vince Vaughn’s character Trent is the embodiment of the Rat Pack Bad Boy.

And when Gossip Girl premiered a decade later, in 2007, the character of Chuck Bass, as played by Ed Westwick, was the epitome of arrogant and supercilious Bad Boy attitude, hedonistic and more focused on money than morality.

Chuck Bass: “I don’t have a romantic bone in my body. Least of all that one.” - Gossip Girl 2x3

One version of the bad boy has a pseudointellectual streak. And he has a dark, cynical take on the world which might sound exciting and insightful at first. But usually, his nihilism turns out to be either shallow — like with Timothee Chalamet’s Kyle in Lady Bird — or dangerous — like with Christian Slater’s JD in Heathers, who’s an actual murderer. Often, it’s both.

Sometimes, the Bad Boy’s defining quality is simply his isolating behavior. Whether he’s intentionally mean to keep other people at bay or committing criminal acts that get him condemned by society at large, a Bad Boy can often be easily identified as a character prevented from establishing meaningful relationships, either by choice or happenstance. James Bond is a perpetual Bad Boy, combining arrogance, outlaw behavior, sexual voraciousness, and stylish cool into a single package. The nature of his work means he will forever be unattached, keeping women at arms’ length, save for sporadic nights of passion.

But underlying all of these different kinds of problematic behavior or misanthropy is a fundamental rule: The Bad Boy only gets away with being Bad because he is extraordinarily attractive. This is the essential element to all Bad Boys. Whether he’s a gangster, a player, or even a vampire, the Bad Boy is defined by good looks, which are the means by which he’s allowed to continue his behavior.

Bad Boys tempt us because they offer a fantasy of making the wrong choice. There’s a thrill to doing what you shouldn’t: Breaking rules is fun.

John Bender: “Being bad feels pretty good, huh?” - The Breakfast Club

In philosophy, this concept is known as “transgression.” Going beyond the limits of conventional behavior, it can mean ignoring, resisting, defying, or refusing to comply with social, institutional, or cultural norms. By doing this, we remind ourselves that we aren’t bound to the expectations of others: We experience the fact of personal freedom. In other words, the Bad Boy literally helps us to feel free.

The Good In the Bad Boy

Bad Boys are almost never wholly bad. There’s a very simple reason for this: We wouldn’t like them if they were. Ultimately, if he doesn’t have any redeeming qualities, then he’s not a bad boy, he’s a jerk. Writer Kat Brzozowski has cited the term “moral event horizon”: the line that separates characters who are redeemable from those who are not. They may not care about the same things we do, but they care about something, and that passion for some value, however abstract, is what keeps them from being just a dirtbag.

A good example of this principle is How I Met Your Mother‘s Barney Stinson. As played by Neil Patrick Harris, Barney is gleefully amoral in most aspects of his life, especially his treatment of women. Barney’s single-minded drive to bed as many women as possible is his primary characteristic for most of the show’s run. But Barney has other qualities that pull him back from the brink of being solely a creep.

Barney Stinson: “Whatever you do in this life, it’s not legendary unless your friends are there to see it.” - How I Met Your Mother 9x17

He’s fiercely loyal to his friends and will go to extraordinary lengths to make their lives better. By demonstrating selfless devotion to his friends, Barney at least partially makes up for his boorish and sexist behavior, keeping himself on the right side of the moral event horizon — at least for most audiences at the time the show aired.

Similarly, Judd Nelson’s character in The Breakfast Club, John Bender, manages to escape total condemnation through a rare act of kindness. Throughout much of the film, Bender is vindictive and cruel to the other kids, leaving him stuck on the “jerk” side of the moral event horizon. But mid-film, the students sneak out to Bender’s locker and realize they’re about to get caught by Mr. Vernon. So Bender sacrifices himself to let the others get safely back to the library without detection. Bender reveals that he’s willing to cause greater grief for himself to help these kids he’s spent the entire morning excoriating—an act of kindness that betrays his nasty exterior. And it leads to the revealing back half of the film, where Bender opens up more and more, becoming a fully three-dimensional person—a necessary element to transition him from jerk to Bad Boy.

The Bad Boy’s Tragic Backstory

One of the surest ways to humanize a Bad Boy is to give them a backstory full of hardship. After all, nothing creates sympathy for a character faster than showing the audience that someone has endured suffering. This has been a core element of most Bad Boys onscreen throughout history—from Jim Stark’s fraught relationship with his father in Rebel Without A Cause to Tony Stark’s fraught relationship with his father in the Iron Man films to Damon Salvatore’s fraught relationship with his father in The Vampire Diaries. (Honestly, it’s a lot of problematic dads that tend to be involved in the backstories of Bad Boys.) And this is another reason the Bad Boy trope is about a form of wish fulfillment: his backstory serves to excuse his more unpleasant behavior. It takes away some of the personal responsibility for his actions, instead chalking everything up to a history he was powerless to do anything about. It takes a complex person and provides an easy out for the badness, simple as a cartoon character.

Going back to How I Met Your Mother’s Barney Stinson, we can see a textbook example of this kind of tragic backstory. It’s revealed that Barney’s mother was a neglectful single parent and that as a child, she offhandedly told him that his father was The Price Is Right’s Bob Barker. Though this storyline is often played for laughs, growing up fatherless is shown as a tragedy, one that created a void in Barney he eventually filled with his meaningless sexual conquests, and that gets mined for real pathos once Barney does meet his real father.

Barney Stinson [Screaming]: “If you were going to be some lame, suburban dad, why couldn’t you have been that for me?!” - How I Met Your Mother 6x19

Here, the Bad Boy is to be pitied, not condemned.

Jess from Gilmore Girls is granted an equally troubled childhood. He also grew up without knowing his father and had a stormy relationship with his mother, who eventually ships him off to live with his uncle Luke rather than deal with him herself. Thus, the modern Bad Boy can never just be bad: There’s a reason for his badness, one which partially—or sometimes even totally—serves as an excuse for his bad behavior.

The Promise of Redemption: The Ultimate Bad Boy Fantasy

What makes the Bad Boy trope so problematic is the way it has historically relied on the lure of heterosexual romance—specifically, the love of a good girl—to rehabilitate the Bad Boy into a Good Guy. The idea that someone so toxic will transform just because a woman commits herself to him has literally been around since the days of Greek myth, but it remains ever-dangerous to sell young women on the false promise that if they would just work hard enough, and sacrifice their own hopes and feelings, the Bad Boy will eventually fall in love with them and become a different—better—person.

Christian Grey: I swore that I would stop it if that’s what it took to get you back. But I am done with it. You mean more to me than anything else.” - 50 Shades Darker

Because the fictional versions of the Bad Boy are made to seem so appealing, we can have hypothetical crushes on them without any issues. But in reality, men who exhibit problematic traits like the kinds we’ve just described aren’t secretly sensitive souls who only need the right woman—they’re cruel, or worse yet, abusive. A recent essay in Cosmopolitan recounts the experience of a woman who thought she had fallen in love with a Bad Boy, only to describe in horrifying detail how being conditioned to accept such behavior eventually led her to accept mistreatment and abuse. This is the truth about real-world Bad Boys—they don’t actually exist. People define themselves through their actions, and someone whose actions are selfish, manipulative, and vindictive isn’t waiting to be saved. They’re in need of serious counseling and treatment — and at long last, the women they have mistreated are starting to be heard.

The Bad Boy is a harmful myth for men, too. The idea that straight women are only attracted to this kind of guy encourages a culture of toxic masculinity where young men are trained to be rude, self-serving, and uncaring of the thoughts and needs of women. In fact, it’s so commonly believed that women are attracted to Bad Boys that there is an entire industry of pick-up artists teaching impressionable boys and men how to be worse people, in hopes of attracting dates. But recent studies have shown that the myth of women preferring Bad Boys is just that—a myth. Plenty of people make mistakes while dating and choose people who aren’t good for them, but this isn’t what anyone wants.

It’s also worth noting when matchmakers and other experts give advice to men on how to “be a bad boy,” practically none of the traits they describe as desirable are the ones actually embodied by attractive onscreen bad boys. For example, Huffington Post’s advice on how to be more of a “bad boy” includes “talk about your experiences” and “be passionate” — even to “Share stories about your family and be animated.” In other words, the exact opposite of the quiet, mysterious bad boy we see in movies and TV. So while the fictional stereotype of the Bad Boy may seem deliciously intriguing in movies and TV, he’s a non-starter in the real world, even if it can sometimes take a while to realize it. We can all love a good version of the Bad Boy in our entertainment—hey, drama is fun to watch!—as long as we remember that’s where Bad Boys belong: in the world of fantasy.

Works Cited

Jacobs, Laura. “Charmed & Dangerous.” Vanity Fair, 21 Feb. 2013.

Brzozowski, Kat. “Beneath the Leather Jacket: Writing with the Bad Boy Trope.” Swoon Reads, 21 Sept. 2016.

Gilmour, Paisley. “I thought my ex was just a ‘bad boy’ - but he was abusive.” Cosmopolitan, 23 Jan. 2020.

Swami, Viren. “Do women really go for ‘bad boys’? Here’s the science that settles the question.” The Conversation, 19 May 2016.

Spindel, Carly. “8 Tips on How to Be a Bad Boy.” HuffPost, 24 Feb. 2016.