Free Character Writing Prompts #50: Criminals

Writing from these character writing prompts about criminals is an open and shut case. While the people who occupy our nation's prisons seem almost alien to us in their actions, they frequently aren't so different from you and I. Whether it be in a state of desperation or of extreme emotions, they took part in an action that will dog them for the rest of their lives. Even if the crime is small in proportion to something like second-degree murder, they may have difficulty getting a job after serving a prison sentence. Those who have been caught committing a crime will typically pay for it and portraying that payment is especially interesting when portrayed in a story. 

Free Character Writing Prompts #50: Criminals

1. After failing to get a job out of high school, on his eighteenth birthday, he decided to take up a life of crime. Three days later, after a failed robbery attempt gone horribly awry, he ended up in jail for the next 20 years of his life. He'd barely had a chance to figure out who he was and now, due to his poor choices, he was stuck. A few years into his sentence he began taking college courses offered to inmates through the prison system and he learned a lot about right and wrong and the kind of person he could be if he put his mind to it. What will life be like for him once he gets out of prison?

2. This master thief had only been caught a few times doing what he did best: steal million dollar jewelry. The only issue for the local police force was that the thing he did second best was smuggling himself out of prison. He was notorious for his escapes and there had even been a television movie created about his exploits. As he grew older and considered settling down, he wondered if he would really be able to start his life over or if he'd always be a petty crook. How will this lifelong criminal learn to live with a life beyond thievery?

3. One of the words frequently used on her in her youth was "innocent," because she looked like she was straight out of a 1950s perfect suburban sitcom. As she got into her twenties, however, no matter how innocent she looked, she nowhere near fit the description, after being charged with several brutal murders of her friends. Her and an accomplice had done an amazing job covering their tracks and two juries had been unable to convict her. Eventually, a third jury came to the correct judgment and forced her behind bars for the rest of her life. How could this childlike veneer be hiding an angry murderer underneath and why did she do what she did?

4. She loved being a woman because it typically predisposed people to think that she was a moron when it came to computers. In reality, she was a world-renowned hacker who would and could steal anything from government secrets to bank account access codes. By dressing and acting like a floozy, she had been able to get out of multiple sticky situations. One or two slip ups though, had her in jail for a very long time. She felt a bit guilty for putting her family through her incarceration and she planned on making it worth their while. What will she do to improve her family's lot and will she consider using her technological expertise to get herself out of prison?

5. This small town young adult had always hated when people acted differently. In school, he was one of the most popular kids because he had perfect looks and an athletic build, and he was brutally mean to those who were of a different race or orientation. He and a few friends got drunk one night and brutally attacked a gay teen who was walking home from work. The teen survived to tell the tale and the small town boy was put away for the next 25 years. He was reviled in the media for continuing to stick by his bigoted viewpoint and in several Internet polls, he was voted the most hated man in America. What would his reaction be upon seeing those polls and what in his upbringing taught him that such acts were the right thing to do?

6. He was supposed to be nothing but a getaway driver. He would take a small cut of the money and then he would use it to pay off some looming gambling debts that were causing him and his family a lot of grief. When his associates killed two security guards at the bank, however, he was made an accessory to murder and he went to jail for over a decade. When he was there he realized how good he'd had it before and a sense of peace washed over him. He became something of a wise man in the jail and even the prison guards began looking to him for advice. What was it specifically about prison that made him so grateful for life on the outside?

7. She hadn't felt in much control whatsoever throughout her entire life. She wasn't traditionally attractive and her great desire to be in a relationship made her take up with some very domineering men. She was extremely lonely and she just wanted to be held some nights. She was a high school English teacher and one of her students became the person she wanted to be with more than anything. She was the boss of the relationship, which she'd never experienced due to the men she usually saw. After she was caught having sexual relations with a minor, she would never be able to teach again and she was sent to prison. Did she feel her relationship was worth it and how will she cope with being labeled a sexual predator?

8. Early in her career as a cop, she was known through the force as one of the toughest, most righteous individuals, regardless of her gender. As the years went on, she grew greedy with power and began manipulating her position unlawfully to get what she wanted. After years of running several money related schemes, she was caught and was sent to jail in a prison populated by people she'd once put away. Life was harder for her there than it ever had been in her early days on the force. What ultimately caused her to cross over to corruption and what is a typical day like for her in her new surroundings?

9. Outside of prison he was one of the most feared mob bosses in existence. In prison, he was even scarier as he'd been put away for life and he had deep connections on the outside. Nobody dared mess with him, prison guards included, for fear that his "friends" would kill family members, even children, of those who treated him badly. Since he was already in prison, there wasn't much investigators could do and they had no idea how he got his messages to the outside so quickly. Due to his larger than life presence, how is he usually treated during a standard day at the prison?

10. During a routine investigation, she had been found guilty of many counts of animal cruelty. She'd run a dog training and breeding facility that had been a public nuisance for years as she'd essentially locked the dogs in a room in the dark, fed them poorly and had neglected to clean up their feces. She'd even killed several of the dogs she'd bred when they wouldn't sell and it was only speculated what she did with their bodies. During her trial she was lambasted by animal rights organizations and local townspeople. When she entered prison, she was treated like scum by animal loving inmates. What caused her to treat animals so badly and why did she take up the business in the first place? 

Did you enjoy these character writing prompts? Buy the full book of 1,000 Character Writing Prompts on Amazon! 

Done with Character Writing Prompts about Criminals? Go back to Creative Writing Prompts. 

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    Written by Bryan Cohen

    Bryan Cohen is the author of more than 30 books, many of which focus on creative writing and blasting through that pesky writer's block. His books have sold more than 20,000 copies. You can find him on and Facebook.
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