The best books with bad boys we love or love to hate

So what if his worldview never makes sense to anyone but himself? I see Holden Caulfield as the quintessential benchmark for a bad boy, shucking off the last few days at the boarding school that expelled him to wander around Manhattan in a daze. Some readers don’t like him so much that they are personally invested in attacking him and what he represents. 

But what is it that he represents, exactly? When I look beyond the surface of his false bravado, he’s a character deeply affected by the death of his brother and is setting out on a quest to understand how to be a real person in a world of phonies. Many of us, as teenagers, also have moments of feeling misunderstood and alone. I know I did, and so did Holden. 

I found it easy to sympathize with Ponyboy Curtis as a victim of circumstance. He’s poor and raised by someone other than his parents, just like I was. More than that, I loved how he doesn’t cling to any of the early illusions about himself, his family, the neighborhood gang, or even the rival gang from the West side. 

Instead, he tries to see things as they are. And even though this 14-year-old punk, who belongs to a “gang of greasers,” discovers how unfair life can be, he still takes it upon himself to give meaning to what is lost. There is something incredibly noble in seeing a smart, empathetic teen wrestling with loss and struggling to be his own person against all odds.

As a bad boy protagonist, I’ve always loathed Gene Forrester and love to loathe him. He starts as a quiet, intellectual student whose best friend and roommate is charming, self-confident, athletic, and a daredevil without being arrogant. Gene even seems to admire his roommate for having all those qualities until we learn the truth. He resents him. 

Like Gene, there were times in my life when playing wingman to a vastly more popular friend could be frustrating, doubly so when they made terrible decisions. Yet, Gene’s journey to the heart of darkness helps put things in perspective. There is no better warning against envy and jealousy than the one immortalized by John Knowles.

The story of Clay Jensen is both beautiful and repelling in that it forced me to consider the unseen impact my insecurities and actions may have had on others when I was a teen. I couldn’t imagine being a shy, bright, and likable California high school student unexpectedly thrust into the center of a girl’s suicide by being named one of the contributors to her death. But that’s the point. Neither can Clay. 

In his case, the only way to discover why he was included is to listen to a set of thirteen tapes made by the victim. These tapes take him on a journey of personal growth and transformation despite his only having the loosest of connections to her. In doing so, he takes us right along with him, considering how our briefest interactions could have profoundly impacted someone else.

I was immediately taken by 17-year-old Justin Bailey because, like him, I didn’t have a strong father figure who could teach me how men were supposed to behave. So when he lands an internship at a legendary muscle car shop, it seems like a dream come true until it quickly becomes clear that his new mentor is equally vulnerable to tragedy.

As his hero falls, Justin falls right along with him—easily lost in his surroundings and eager to accept one justification after another until he succumbs to the darkest of temptations. As a protagonist, his only saving grace is understanding what he did was wrong, albeit too late. And at the same time, it reminds me that the most dangerous unreliable narrator could be me.