57 books like Desperadoes

My name is Tim O’Leary and two of my books, Dick Cheney Shot Me in the Face–And Other Tales of Men in Pain and Men Behaving Badly, emanate from the minds of protagonists trying to do the right thing the wrong way or evil characters doing the wrong thing they believe to be right. I’m particularly drawn to those wonderful literary psychopaths that draw you in with compelling personalities, while reviling the reader with their heinous actions. 

I’m an old guy. I say this with a bit of cheek and a certain amount of incongruity. All the books on my list are old. That’s one area of continuity. Another, and I’ll probably stop at two, is that they all deal with ordinary people caught in extraordinary circumstances—those curveballs of life we flail at with an unfamiliar bat; the getting stuck on the Interstate behind a semi and some geezer in a golf cap hogging the passing lane in a Buick Le Sabre. No one makes it through this life unscathed. How we cope does more to define us than a thousand smiles when things are rosy. Thus endeth the lesson.

As the sex and relationship advice columnist at Men’s Health Magazine, I’m obviously pretty damn obsessed with sex. I find it fascinating on so many levels, which is why I not only have a ton of it but also made it my career. For so long, I struggled with sexual shame, and one thing I realized as a writer is that I’m not special. Sure, I’ve probably been to more sex parties than you, but if I’m struggling with shame, being bisexual, and embracing my kinks, then other folks are, too. And just like I’m obsessed with sex, I’ve become obsessed with helping others remove sexual shame.

I was an English major in college and my dream was to write the Great American Novel. My literary heroes were writers like Saul Bellow, Philip Roth, Bernard Malamud, Jean Rhys, Margaret Drabble, Truman Capote, and Norman Mailer. They “taught” me how to write. About a dozen years ago, I concentrated on writing crime novels, like Swann’s Last Song and Second Story Man, both of which were nominated for Shamus Awards (Second Story Man won the Beverly Hills Book Award.) I'm a magazine journalist and write nonfiction books, screenplays, plays, and book reviews. I teach writing here in New York City, and I’m on the Board of PrisonWrites and the New York Writers Workshop.

Incarceration is a gigantic problem in the US, especially because of its connection to racial injustice. I have no firsthand experience with prison or the system, and yet it looms large in my imagination and my deepest fears. That should not be the case merely because I’m a Black gay American, but here we are. I feel that with the help of my mother and others, I have managed to sidestep a lot of the potential pitfalls of people’s misguided perception of my identity, but I have an active, paranoid imagination and profound survivor guilt, so I gravitate toward stories about people at who are odds with our society in ways that reflect that precarious status which allows me to explore a wide range of human experiences.

Because I grew up in the 1950s and ’60s, my supply of heroes was liberally doled out by the 130+ Western series that dominated nighttime televisions. My parents allowed me one program per week. It was a Western. I was soon interested in history, to know what really happened in the American West, and so I came to understand the great discrepancies between fact and TV. The truth, for me, is much more interesting than the myth. But that truth carries some heavy weight, which informs us of our national foibles, crimes, and embarrassments. As a Western historian, I've done my share of historical research, but I still gravitate toward historical fiction as a writer.

Because I grew up in the 1950s and ’60s, my supply of heroes was liberally doled out by the 130+ Western series that dominated nighttime televisions. My parents allowed me one program per week. It was a Western. I was soon interested in history, to know what really happened in the American West, and so I came to understand the great discrepancies between fact and TV. The truth, for me, is much more interesting than the myth. But that truth carries some heavy weight, which informs us of our national foibles, crimes, and embarrassments. As a Western historian, I've done my share of historical research, but I still gravitate toward historical fiction as a writer.

Because I grew up in the 1950s and ’60s, my supply of heroes was liberally doled out by the 130+ Western series that dominated nighttime televisions. My parents allowed me one program per week. It was a Western. I was soon interested in history, to know what really happened in the American West, and so I came to understand the great discrepancies between fact and TV. The truth, for me, is much more interesting than the myth. But that truth carries some heavy weight, which informs us of our national foibles, crimes, and embarrassments. As a Western historian, I've done my share of historical research, but I still gravitate toward historical fiction as a writer.

I’ve found kids to be interested in difficult topics - like stealing, racism, inequality, environmental catastrophe to name a few! But I don’t want to lecture or frighten them about their future. I believe picture books can tell a story about things going awry but coming right again through a good idea, or act of kindness or a magic wand or the intervention of fate. When the story unfolds in the comfort and security of a carer’s lap or a safe classroom and there are accompanying pictures of absorbing detail that communicate the artist’s emotion and humor I think you provide universal foundation blocks for a good life.

Because I grew up in the 1950s and ’60s, my supply of heroes was liberally doled out by the 130+ Western series that dominated nighttime television in those decades. My parents allowed me one program per week. It was a Western. I was soon interested in history, to know what really did happen in the American West, and so I came to understand the great discrepancies between fact and TV. The truth, for me, is so much more interesting than the myth. As a Western historian, I've done my share of historical research, but I still gravitate toward fiction as a writer. I love the freedom to engage my characters’ thoughts and emotions.