From top left to right: Rope, Compulsion, Swoon, Murder By Numbers

Decades before the O.J. Simpson case, there was already a “crime of the century” for the 1900s. Now nearly a century old, the case still has a long-standing impact, not just where it happened (Chicago) but in our culture overall: Multiple movies have been made about it, with such actors as Dean Stockwell and Ryan Gosling playing one of the culprits in question. Even if you’re not sure who, exactly, these names belong to, you’re likely familiar with the phrase “Leopold and Loeb.”

Nathan Leopold and Richard Loeb were two beyond-gifted teenagers in the high-class neighborhood of Kenwood (where the Obamas have a home), near Hyde Park on the South Side of Chicago. Both had graduated from college before the age of 20. In 1924, 18-year-old Loeb was in graduate school, and 19-year-old Leopold was in law school. Studying the works of Nietzsche, the pair decided to try to pull off the “perfect crime,” just to see if they could get away with it to prove their superior intellect. Unfortunately for young Bobby Franks, fellow Kenwood native and Loeb’s cousin, their perfect crime turned out to be murder.

Leopold and Loeb in court (Photo: George Rinhart/Corbis via Getty Images)

One night Loeb and Leopold randomly came upon 14-year-old Franks, picked him up, and killed him in a rented car. They ditched the body near Wolf Lake in Indiana, where Leopold liked to go bird watching, and dummied up a fake ransom note written on a stolen typewriter for the Franks family. But the Franks had already called the police, and the body had already been discovered by the time the note showed up. The case was solved relatively quickly. The super geniuses were felled by some rank amateur moves: Leopold lost his glasses near where they stashed the body, and the glasses’ unique hinge made it easy to trace back to him; the car rental, plus stolen typewriter, discovered in one of the boys’ bedrooms, also connected them to the crime.

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Lawyer Clarence Darrow pleads case for Leopold and Loeb. (Photo: NY Daily News Archive via Getty Images)

When the murderers were discovered, it was their lack of remorse that staggered a nation already suspicious of the new 1920s youth culture. The case of Leopold and Loeb actually elicited the term “thrill killing,” as their crime was not personal or one of necessity, but committed just to see if they could get away with it. The murder was also pointed to as a bonding mechanism between the boys, and a sexual relationship was implied between the two. In another noteworthy twist, their desperate and wealthy families hired attorney Clarence Darrow to argue to save the boys’ lives in court. Darrow was usually known as a defender of the weak and helpless, but he hated the death penalty. Since the prosecution was aiming to hang Leopold and Loeb for the senseless murder of a child, Darrow thought he could use this high-profile case to make an argument to get the boys a lesser sentence. He succeeded after an impassioned closing argument, and Leopold and Loeb went off to prison. They were eventually reunited at Stateville Penitentiary, where they developed an educational curriculum for the prison school system. Loeb was stabbed to death in 1936 by a fellow inmate; Leopold was released on parole in 1958, got married, and shied away from the spotlight as much as he could for the rest of his life.

You would be hard-pressed to write a better detective story—cocky young murderers felled by their own arrogance and a number of leading clues—which may be why the Leopold and Loeb case is a well Hollywood has returned to. The first person to turn the case into a movie, unsurprisingly, was Alfred Hitchcock. Based on a stage play, the 1948 film Rope is most famous for Hitchcock’s showy filming, with long, continuous shots implying the rope of the title; film canisters were refilled during close-ups on dark suit jackets, allowing the shots to appear even longer than they were.

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The movie starts out with “the perfect victim for the perfect murder,” as Brandon (John Dall) and Phillip (Farley Granger) strangle their childhood schoolmate David with a rope and dump him in a trunk, which they then ghoulishly turn into the centerpiece table at a dinner party. The movie establishes the Leopold and Loeb archetypes that the 1920s public had become familiar with thanks to the media frenzy that hounded the case: the Richard Loeb character (Brandon) is charming, charismatic, and ostensibly the one in charge, while the Leopold (Phillip) is dark, brooding, and more insecure. Brandon quickly spells out the murder’s motivation—“killing for the sake of danger and the sake of killing”—and states that “the power to kill can be just as satisfying as the power to create.” He also calls out the “difference between us and ordinary men.” The implied romantic relationship between Brandon and Phillip caused the film to be banned from several theaters.

James Stewart plays Rupert Cadell, the boys’ old headmaster, now a publisher, who initially jokes about murder as an art form at the dinner party and suggests that the random killing of people could help alleviate lines for theater tickets and restaurants. But when David, the supposed guest of honor, never shows up, Rupert begins to suspect the worst.

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Rope treats the original murder as inspiration for its cat-and-mouse drawing-room drama. Hitchcock, as usual, expertly builds the suspense, as the tension eventually leads to Phillip unravelling and Rupert discovering the truth. There’s an especially brilliant sequence when the party crowd speculates on where David might be while the trunk he’s stashed in is in plain view. Then the maid attempts to clear it off and nearly opens it before one of the murderers stops her. Like the real murderers, Brandon and Phillip are felled by a small detail they’ve overlooked: David’s hat, which Rupert discovers in the hall closet. But Rupert’s status as the boys’ old teacher, aided by the considerable screen presence of Stewart, adds a necessary heart to Rope. Rupert is undone at the end of the movie when he realizes that all of his late-night chats with Brandon about “superior and inferior people” have had the worst effect imaginable; he is horrified, and on some level, feels as guilty as Phillip.

The Leopold and Loeb case is treated much more literally in 1959’s Compulsion, which includes so many of the actual details that it’s a wonder they bothered to change the names. Future Falcon Crest star Bradford Dillman and future Quantum Leap star Dean Stockwell play Loeb (Artie) and Leopold (Judd), respectively. Stockwell was already well-established as a child actor, which makes his Judd an intriguingly complex character, possibly even sympathetic, as it appears he was an antisocial loaner who got goaded into the killing in an effort to please the much more popular Artie. But Compulsion neatly sets out everything that snared the real pair of killers: the glasses, the typewriter, the turned-on-each-other confessions (each says the other was the one to deliver the fatal blow). And it casts none other than Orson Welles as the Clarence Darrow stand-in, who saves the boys’ lives by arguing that their superior intellect put them at a disadvantage and that no sane person could kill just for fun. He also argued strongly that their youth made them more sympathetic. In real life, Darrow’s closing arguments took three days. Here, while Welles’ lawyer’s impassioned speech also spares the boys’ lives, by the end of the film he seems as disgusted with them as the rest of the world is.

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Director Tom Kalin released Swoon in 1992, an indie film that took a documentary angle to the case and is the only one here to focus on Leopold and Loeb’s sexual relationship. Despite all of his bragging about his intellect, Leopold was a follower and in Loeb found someone to worship. In the court testimony, it was implied that Loeb demanded that Leopold commit criminal acts in exchange for sexual favors. Despite the protest by Rope audiences, the only other cinematic hint we have of this relationship is when the Loeb character calls out the Leopold character for ditching him “for a girl” in Compulsion and 2002’s Murder By Numbers (more on that below). Swoon did not make much of a ripple beyond a few regional film festivals, but helped revive the interest in the decades-old case, possibly leading to its next cinematic incarnation.

The oddest and perhaps most effective cinematic version of the case is the furthest removed, time-wise, from the actual crime: 2002’s Murder By Numbers. Director Barbet Schroeder was adept at helming thrillers—like Single White Female and Kiss Of Death—as well as based-on-fact drama, like his Reversal Of Fortune. Here he translates the Leopold and Loeb case for a new century, making it just as compelling as it was years earlier, possibly because it’s also the role where Ryan Gosling first made an indelible mark; his Loeb (even helpfully named Richard) does indeed appear charming enough to talk Michael Pitt’s Leopold character Justin, or anyone, into murder. Sandra Bullock is the rogue cop determined to take them down. The clues are different—a footprint, some carpet fibers—but the unraveling happens just the same, though with a dramatic hanging-over-a-cliff ending. Perhaps the most chilling scene in the movie is when Richard and Justin pick their victim in a grocery store parking lot. As with the real Leopold and Loeb, the selection is completely random, and they know they look like such upstanding young people that they’ll be able to approach any young woman without fear of suspicion, just as young Bobby Franks got into that car likely without a second thought, leading to the loss of his life.

Murder By Numbers is the most recent Leopold and Loeb version, but it probably won’t be the last. Like many dark stories of Chicago history from a century ago—the reign of Al Capone, the Black Sox, the murder castle at the 1893 World’s Fair—the story has so many key, sensationalist elements that keep it timelessly fascinating. It also has a comeuppance ending that would be perfectly satisfying if it didn’t follow such a horrible tragedy. Leopold’s glasses are even currently on display at the Chicago History Museum’s Secret Life Of Objects exhibition, because, as the museum’s vice president John Russick told CBS, decades later “we’re still talking about this case.” That the Leopold and Loeb case still resonates is almost heartening: Even now, it still seems inconceivable to most people that anyone would take a human life for the random “fun” of it.

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