Fans pick 96 books like Leopold and Loeb

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.  

This pick is not without some caveats. This book, Nathan Leopold’s autobiography, was written while he was trying to get paroled from prison and it has to be taken in that context.

There are lies and omissions, but there are also harrowing sections describing the brutality that prisoners faced in the 1920s and genuine emotion when he discusses his complicated feelings for Richard Loeb. There’s no better place to go for information about his life in prison, or to get a feel for his personality, as long as you can read between the lines and remain skeptical when things seem a little too good to be true.

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.

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.

In 1920s Chicago, the theater and the courtroom collided as a pair of men dropped dead in the vicinity of beautiful, duplicitous women. The musical Chicago has always been one of my favorites, and I was delighted to read this book about the real women who inspired Velma Kelly and Roxie Hart. It did not disappoint.

Douglas Perry tells the story of Beulah and Belva with all the flair and drama of the musical. I will never forget reading about how callously Beulah Annan sipped cocktails and listened to music for hours as her lover lay bleeding on the floor. It sent chills down my spine.

Lynching is central to the late 19th century and thus the theme that I explore in my recommendations, but Shepherd.com covers this tragic subject elsewhere. Instead, for my last book, I offer Adler’s study that explains the persistently high and even increasing rates of violence and homicide in Chicago during an era when varied modern social controls—urban reform, the discipline of the factory floor, expanding education and the bureaucratic state—swept over that city as they did over America, too. According to older theories about social turbulence and murder, these should have declined. Instead, the opposite was true, though the forms that violence took did change. Perhaps it was Adler’s intention to leave frighteningly unanswered what it is about people generally, and Americans specifically, that the dark impulses they have run so deeply that they are impervious to social control.

If screwball detective fiction intrigues you, you must read Craig Rice. Why not start with Eight Faces of Three, the mystery introducing the wacky, rye-soaked team of Jake Justus, Helene Brand, and John Joseph Malone?

Justus is a good-looking press agent and the book’s moral center; Brand is a gorgeous heiress and non-stop partier; and Malone is a stumpy lawyer-slash-PI with good instincts and better luck. Imagine Philip Marlowe meets the Marx Brothers.

In Eight Faces of Three, a young woman awakes to find her aunt murdered, all the house’s clocks set to 3 am, and herself the prime suspect.

Craig Rice was the first mystery writer to grace the cover of Time magazine. Her private life was strewn with ex-husbands and empty booze bottles, and she died way too young at 49.

However, her literary legacy—one critic dubbed her the “Dorothy Parker of detective fiction”—will keep her… show more.

Using photo and newspaper archives from the Chicago Tribune, the authors of He Had It Coming tell the stories of four Chicago female murderers from the 1920s.

The documentation (both primary and secondary sources) and, especially, the newspaper's original high-quality historical photographs inspired me to dig deeply into similar archives when researching and writing my book.

The perfect murder is not possible, right? Well…this book may have changed my mind! I don’t generally like brooding, self-absorbed characters, but Simon–ah, Simon, odd and way past cute-quirky. But somehow, Ellis makes him a compelling character. And the twists in what at first glance is a typical murder mystery with a spurned lover, a big trust fund, and lots of lies make a sharp 180-degree turn in the final pages.

As puzzles go, this book has it all. Dark history, long-held grudges, cross, double-cross…is triple-cross a thing? If not, it should be after this ending. And beware the Grim Reaper next Halloween!