85 books like Life Plus 99 Years

Despite being published in 1975, Hal Higdon’s book about the Leopold and Loeb case remains the definitive account, at least to me.

If you’re looking for a factual, in-depth look at the crime, investigation, and sentencing hearing, look no further. Higdon was able to interview and correspond with dozens of people who were close to the case and who personally knew the killers and victim. He weaved those recollections into the narrative along with newspaper reports and quotes from the court documents in addition to the rest of his vast research, which gives his book a wonderful richness and depth. 

There have been many, many fictional adaptations of the Leopold-Loeb story, and it seems to be tricky to get the details and the people portrayed accurately, while still telling a tight and intriguing story. This play achieves that the best that I’ve seen.

Told in a non-linear fashion, it explores a nuanced relationship between Leopold and Loeb and what led them to the murder, as well as the arguments of the lawyers and the vitriol of the press. Exploring themes of prejudice, love, and mob hysteria, the audience gets to see many angles of the case and feel the vast effect it had on the city, without losing the more nuanced explorations of the characters and their struggles.  

The Hunting Accident is a graphic novel that explores a fictionalized version of the life of Matt Rizzo: a prisoner whom Leopold knew in the 1930s.

While the book is more focused on Rizzo’s story, Leopold also plays a big part, and I recommend it because it’s a very unique way to experience this story. Rizzo was blinded while committing the crime which got him sent to prison, and the book focuses on Rizzo adjusting to living without his sight while Leopold adjusts to living without Loeb, who was murdered shortly before Rizzo’s arrival.

The artwork is detailed and sometimes disturbing as it portrays the pair navigating the prison and searching for purpose, connections, and meaning in their lives. 

If you’re someone who would like to dive more deeply into the sources from the case, this book is a great place to start.

The book’s author, Maureen McKernan, wrote half a dozen articles for The Chicago Tribune about the case in 1924, and then worked with defense lawyers Clarence Darrow and Walter Bachrach to compile this primer of the important facts and sources. In addition to a solid summary of the case, this book contains large portions of the actual confessions, psychiatric reports, testimony, speeches, and the Judge’s final decision from the hearing itself.

As the book was published in 1924, there are omissions of some subjects, notably homosexuality, but this is still an excellent introduction to deeper research.

In 1924, fourteen-year-old Bobby Franks was kidnapped and murdered by Nathan Leopold and Richard Loeb, two highly intelligent college students who felt they were above the law. Attention to detail is what kept my interest in Leopold and Loeb. It starts with the two men planning the kidnapping, the murder, and their eventual arrest. The techniques used to garner confessions are highlighted, and reading about the legendary Clarence Darrow, who defended the killers, was fascinating. This is another great true-crime read that delves into Leopold’s complete lack of emotion regarding the killing.  Caplan has done an outstanding job detailing this tragic case.

We’ll start with another novel (there are many) inspired in part by the Leopold and Loeb crime. This one swaps Chicago for Pittsburgh, and changes their mismatch in IQs for a stark class divide.

One of the variations I most enjoy in this retelling is that university students Paul Fleischer and Julian Fromme are both damaged when they meet. Julian is scarred physically from a car crash in his youth, and Paul is still recovering emotionally from the death of his father.

Additionally, since the book is set in the 1970s, their sexual involvement with one another is more explicit than the original story could allow (though it still comes with social stigma).

A captivating work of dark academia and crime, the obsession between these two compels them to court their own ruin.

Nathan Leopold and Richard Loeb set out to commit the perfect crime and ended up in newspapers as the perpetrators of “the crime of the century.” They kidnapped and murdered a teenage boy in Chicago in 1924, but both Leopold and Loeb were still considered boys themselves at the time. Clarence Darrow defended them at trial, arguing that they were guilty but that the situation had extenuating circumstances. Baatz’s book explores how two college students from good families ended up in prison for murder. Leopold’s family even came from Michigan’s Upper Peninsula, near where I currently live, so even though the case is almost 100 years old, it’s not as distant as it might seem.

Although this novel is not necessarily ‘apocalyptic,’ I couldn’t help but include it. Alexander Gordon Smith’s Lockdown is a high-stakes novel that follows Alex, a teenager who is wrongly accused of murder and sentenced to an underground prison. The Furnace Penitentiary is not a normal prison, but is a building where inhumane experiments take place. I’ve always been fascinated by characters who have to survive in an environment they cannot physically leave, and the Escape from Furnace series does this beautifully.

Unlike my other recommendations, this book takes a longer historical view of the prison and also provides a more sociological framework for understanding trends in penal history, focusing on the prison but also its sister punishments like parole and probation. Breaking the Pendulum focuses on the full history of the prison in the United States, from its origins to now. But more importantly, it synthesizes the state-of-the-art knowledge from punishment studies about how to think about and understand punishment: points like recognizing geographical variation rather than focusing on the national picture and recognizing that even periods that seem to be fairly homogenous in their penal policies are actually periods with a lot of hidden debate.

From there, it moves away from the standard narrative of a pendulum swinging between punitive and rehabilitative or liberal and conservative approaches to punishment to a more accurate and mixed picture, and for thinking about… show more.

After the news came out that Norman Mailer was writing a book about the life of Gary Gilmore, which came to be his magnum opus, The Executioner’s Song, he received a letter from a convict named Jack Henry Abbott. An avid reader of philosophy and literature who was also serving a life sentence, Abbott wrote to warn the renowned author against misapprehending American prisons and to teach him how to write about the violence of incarceration. The two men exchanged long, detailed letters. Eventually, Mailer collected Abbott’s letters in this book. In his letters, in a tone both detached and lyrical, Abbott writes unforgettably about what spending long years in prison does to one’s soul and body. In my view, the letter on solitary confinement is the finest and most harrowing chapter of this book.