[Having been laid up with the flu, I have not had a chance to post anything new here in a while. But I've revised and corrected a previous article on Leopold and Loeb that I wrote back in the spring. Enjoy. -- Brooks]

Strange Bedfellows: The Legacy of Leopold and Loeb

Earlier this year, while killing time at the Harry Ransom Center in Austin, Texas (during a lull in my research among its amazing Ziegfeld Follies memorabilia), I stumbled by chance upon a mention of Erle Stanley Gardner’s papers in its catalog. Since, as is obvious by an earlier entry on my blog, I have become obsessed with all things related to Perry Mason (see here), I decided to take a quick gander at this intriguing collection. I couldn’t believe what I found! It’s a vast treasure trove of materials relating to mystery novels and true crime, in particular, “the crime of the century.”

Gardner was a tireless workhorse and wrote or dictated reams of prose every day: letters, proposals, lectures, novels and essays. He wrote at least two Perry Mason novels a year, as well as countless others under various pseudonyms. His correspondents numbered into the thousands. He seems to have replied to every fan letter he ever got. His collection runs to over 33,000 items, and includes a replica of his writing studio from his California ranch. It would take a lifetime to pore through, which might explain why there hasn’t been a biography of him written since the 70s. Not even Della Street could make sense of it all. But a reference in the center’s collections guide’s witty “Gay Lives” section (which in a funny twist turned out to be written by John B. Thomas, a friend of mine) led me directly to a pair of folders of letters between Gardner and Nathan Leopold, the luckier half of the infamous duo Leopold and Loeb.

Leopold and Loeb? Those notorious Nietzschean nihilists? Those kinky “killers for kicks”? “Babe” and “Dickie,” as they were nicknamed by their loving parents and later by the tabloid press, were the star-crossed lovers of crime. Their tragic folie à deux was a twisted inversion of the traditional Shakespearean romance. But rather than kill themselves for love, they took the life of an innocent 14-year old boy.

On a summer day in Chicago in 1924, these two handsome teenagers from well-to-do Jewish families kidnapped a young school friend, Bobby Franks (Loeb, who was a cousin of his, had played tennis with Bobby just the day before), and murdered him in cold blood by beating his head in with a cudgel. Then they poured hydrochloric acid over his genitals and face, and stuffed his nude corpse into a culvert before demanding $10,000 in ransom from his parents for his “safe return”. Why in hell? “For the thrill of it,” they said, coolly and without apology.

Clarence Darrow, above, of the later Scopes Monkey Trial fame, defended Leopold and Loeb and saved them from the death penalty. At the time, their diabolical actions were dubbed “the crime of the century,” even though the new century was not much older than the youths themselves. But in some ways the title still stands since the senselessness and naked cruelty of their crime was never equaled. Far worse things were done in the decades that followed. But no single event had the resonance of this inexplicable act.

The boys’ homoerotic attachment to each other gave their maniacal compact as amoral “Supermen” an added frisson of blood lust, at a time when such subjects were strictly taboo. A court specialist, talking about Leopold, revealed that even in jail “a look at Loeb’s body or his touch upon his shoulder thrills him so, immeasurably.” During their trial the judge refused to let the jury, or any women and reporters in attendance, hear the sordid details of their peculiar sexual predilections. This only added to their notoriety, even if references in court to “mouth perversions” and “interfemoral intercourse” were edited out of news accounts or sealed as privileged testimony. In time, rumors fanned by scandal rags and malicious gossips would add whole new dimensions, including necrophilia, castration and rape, to their crimes, tarring them as vicious sodomites as wicked as Gilles de Rais and Jack the Ripper. But the truth is that their crime was absolutely arbitrary and pointless. There was no sexual gratification and no previous pattern of sadistic behavior.

It was ultimately, however, despite their best laid plans, a very imperfect crime, poorly thought-out and executed. They never got the ransom money and were quickly caught. The acid they used concealed nothing, and the eyeglasses Leopold accidentally left (a Freudian slip?) at the scene sealed their doom. Both confessed too easily and immediately blamed the other. In fact, the “crime of the century” was an inept fiasco. And yet rarely has a pair of such mismatched misfits generated so much media attention! Their case has captivated each new generation of writers, jurists, psychiatrists, criminologists, filmmakers, and artists. Perhaps their story is so popular because of their failings, their tragic flaws, which render them more human, less evil. For the truth is that Leopold and Loeb were no different than the rest of us.

There’s no need to go into further specifics here of the killing and the subsequent trial. The casebook has been well-documented on numerous websites and several informative blogs, including this one.

The curious friendship between Erle Stanley Gardner and Nathan Leopold, above, began shortly after Gardner reviewed the novel Compulsion, by Meyer Levin, for the New York Times in 1956. Gardner praised the novel, which was a fictionalized account of the case, as a “masterly achievement in literary craftsmanship.” He wrote candidly of the unique aspects of the Leopold and Loeb story: “When two child prodigies, the highly educated sons of wealthy families, were found to have been experimenting in homosexuality and then went out to commit murder just for the sake of the experience, society shivered with a premonitory thrill.” The key thing here is that Gardner understood that the “thrill” of the kill was just as much in the minds of the American culture that devoured each new revelation as it was for the boys who did it.

At the end of his review, Gardner took issue with Levin’s conclusions, stating that “the last chapter has been omitted.” He wanted to know: “What has happened to the one central character who has remained alive?” That is — Nathan Leopold. It was an open challenge. And one that Leopold responded to immediately. Days later, Leopold wrote a fawning letter to Gardner, thanking him for his supportive words about his right to rehabilitation and telling him how much of a fan he had always been of his Perry Mason novels. Leopold was limited in the number of letters he could write, and had to include his prison number “9306-D.” All his letters were read and approved by censors.

Gardner, who seems to have been flattered by Leopold’s admiration, quickly wrote back and began a lengthy correspondence that led to a close friendship for the rest of their lives. Gardner also ended up writing the introduction to Leopold’s memoirs Life Plus 99 Years. The latter helped Leopold eventually get parole, as did efforts by Gardner and his team at the Court of Last Resort, a legal think tank that Gardner established which took on special cases and examined the pros and cons of rehabilitation. The Court became a popular TV show and book. And in 1957 Gardner’s most famous creation, Perry Mason, was lighting up the tube, with Raymond Burr bringing justice to his falsely accused clients week after week. So it’s no wonder that Gardner was drawn to Nathan Leopold’s predicament. He loved a tough case as much as Perry Mason.

The notion that a confessed killer who barely escaped the death penalty could ever get parole seemed far-fetched when Leopold and Loeb first went to prison. But by the late 50s, public opinion on prison reform had changed dramatically and Leopold saw a way out. This was partly in response to the wave of juvenile crime sweeping across the nation, a point Gardner hammered home in his introduction to Leopold’s memoir. Leopold’s crimes no longer were so singular, or so scary, he said. Far worse things were happening everyday across the country. In fact, the Clutter family murders which Capote immortalized in In Cold Blood were just around the corner. Gardner, along with Carl Sandburg and Elmer Gertz, who represented Leopold, managed to convince the parole board that Nathan Leopold deserved a second chance. He was finally released from prison in 1958, having served 33 years of his life sentence. By then the press, rather than calling Nathan “Babe,” began to call him “Pudgy.”

I find the exchange between Gardner and Leopold fascinating. It’s not often, I would think, that a convicted murderer develops a friendship with a mystery writer and manages to get this famous author to write for him. (Norman Mailer comes to mind but he was not a mystery writer so the connotation is different.) The friendship between Gardner and Leopold is paradoxical too because the entire notion of the “perfect murder” which had been Loeb’s idée fixe stemmed from his reading pulp detective fiction of which Gardner was one of the earliest masters. No doubt for Leopold this added a level of nostalgia to his interplay with Gardner since it had to remind him of Dickie Loeb. He must have been tickled pink by the irony of it all.

The symbiosis throughout the correspondence between Gardner and Leopold is revealing too of Leopold’s uncanny people skills. In all his letters, Leopold is a master at flattery and charm. He downplays his talents and paints Gardner as an extremely generous man who risked his reputation to take on Leopold’s case. Leopold constantly criticizes his own prose style and laughingly admits that he only wanted Gardner to write the introduction so that the reader wouldn’t be too disappointed in the final product. It’s a clever ploy to win over the immensely successful author (who never really achieved literary recognition for his immense output, and only won an Edgar award for his non-fiction book The Court of Last Resort). Leopold must have known that by stroking Gardner’s ego he was nudging the door open to his own freedom.

But there’s no denying that the friendship was genuine. Leopold may have seen the advantages of his connection to a famous writer who went out on a limb to help him achieve parole. But the affection seems completely real and definitely mutual. In one letter Leopold offers to put up Gardner in his tiny apartment in Puerto Rico (after his parole) if Gardner were to visit. The idea of Gardner shacking up with this notorious killer is too good to be true. It’s not clear from the correspondence if Gardner ever took him up on his offer.

What is most surprising about this cache of letters is that no one seems to have read them, at least not in the context of the literature surrounding the case. Hal Higdon’s book The Crime of the Century (Putnam), which came out in 1975, makes no mention of Gardner at all. Likewise in the latest book on the case: Simon Baatz’s For the Thrill of It: Leopold, Loeb, and the Murder that Shocked Chicago (Harper, 2008) Gardner’s name does not appear anywhere within its more than 500 pages despite the fact that he was instrumental in helping Leopold get parole. Leopold, himself, said to Gardner that he was the single most important person in helping him achieve it. He was deeply grateful.

In explaining why he felt it necessary to write his new book, Baatz boasts about its importance and uniqueness. He seems to think very little has been written about the case in the past (although John Theodore’s Evil Summer, a scholarly examination of the crime, had come out in 2007 from the Southern Illinois University Press), and makes the odd assertion that Higdon’s book was merely a hack job, even though it was a thorough piece of detective work which revealed a lot of new material, and helped unravel the “ABCD murders” for which Loeb and Leopold had also been implicated.

Baatz also goes off on long tangents about the myriad lawyers and judges involved. He quotes endless reports from the various physicians and “alienists” of the day who examined the two boys. And yet he offers little insight of his own into the mindsets of these troubled youths. (For a much more rewarding take on the case read Paula S. Fass’s brilliant essay, “Making and Remaking an Event: The Leopold and Loeb Case in American Culture.” HERE.)

When discussing the murder, Baatz relies on Nathan Leopold’s version of events, firmly planting Richard Loeb in the backseat, despite the fact that no one knows for sure who committed the actual cudgeling, and Loeb always claimed Leopold did it. Likewise when Loeb is slashed to death in jail in 1936 by punk convict James Day, the author takes the killer’s version of events as gospel. Day claimed he killed Loeb after he made unwanted advances, and he’d wrestled a razor away from him. But evidence was later submitted that James Day had brought the stolen razor in with him and had most likely been set-up to kill Loeb. In fact, Loeb was sliced to death with 56 separate gashes, some as long as two feet. His jugular vein was severed. Despite the grisly details, Clarence Darrow stated at 79 years of age: “I’m glad he’s dead all the same. He’s better off than Leopold.” As for James Day, below; he was found not guilty of murder.

No citations are offered by Baatz for any of his coverage of Loeb’s mysterious murder. He also uses the Chicago Daily Tribune as his source for assertions that Dickie Loeb often had sex in prison with other male inmates, something which many involved in the prison, or who studied the evidence later, either questioned or denied. (Although there is a very interesting letter in the Gardner files from a writer who claims both Loeb and Leopold preyed on inmates.) Loeb’s cellmate Edward Steplowsky claimed Loeb was busy writing a history of the Civil War, and objected whenever Ed turned on the radio. He does not sound like someone chasing punks in shower rooms. Even if it were true that Loeb had lovers in jail, which is certainly understandable, it seems pointless to footnote a newspaper of the period as proof of his predatory behavior since newspapers are notoriously unreliable, and so much better stuff has already been written about it. Nevertheless, it’s helpful to read the book. It never hurts to refresh one’s memory about the specifics of the Leopold and Loeb case.

Like many, I first learned of these two infamous “thrill killers” by watching Compulsion (1959) starring Orson Welles (above). Directed by Richard Fleischer, it’s a potent, underrated film, which thanks to a new DVD release is having a much-deserved second life.

Based on the Levin novel, the movie takes a psychoanalytic view of the case. Dean Stockwell played the part based on Nathan Leopold with a sad neurotic genius while Bradford Dillman took on the smooth, devil-may-care Dickie Loeb in his usual deft manner. Welles’s take on Clarence Darrow is a sight to behold and proof that he was as great an actor as he was a director. Apparently, however, he was a difficult cast member and took off for Mexico before looping was finished. His closing remarks, Dean Stockwell once stated, had to be pieced together from leftover scraps by a clever editor.

What most of us have forgotten is that Compulsion first ran on Broadway as a stage play, above. It was part of Zanuck’s option when he purchased rights to the novel that Levin had to write a dramatic version which would open prior to the film, generating word of mouth and advance hype. Levin eventually disassociated himself from the staged play, after arguments with the producer Michael Myerberg who brought in Robert Thom to revamp the script. Levin later published his own edition of the play (Simon & Schuster, 1959) with a long foreword discussing his battles with the producer.

The play opened in October, 1957 at the Ambassador Theatre with Dean Stockwell in the Nathan Leopold role (he was trying to break out of his earlier goody-good child star roles) and Roddy McDowall, above, (who also needed to move away from being typecast in his Lassie vehicles) in the more glamorous Loeb part. Included in the cast were Howard da Silva, Frank Conroy (who ended up having a near-fatal heart attack during the run) and a very young Suzanne Pleshette as “the Fourth Girl.” Cy Coleman provided the music! It ran for 140 performances. Critics didn’t warm to it much, finding it “muddled” and “too long”. But audiences lapped up its weird psycho dramas, especially when Roddy McDowall cried out: “I want my Teddy Bear!”

Nathan Leopold hated Compulsion, although he acknowledged that Meyer Levin had done a good job of weaving fact with fiction. Too good a job, apparently. Leopold said he threw up after reading it. His biggest complaint was that Levin had only interviewed him for about an hour and made a lot of his assumptions on Freudian theory rather than on the evidence. No doubt Leopold must have been shocked by the innuendoes in the novel about his obsession for Loeb. He ended up suing Levin, Zanuck and others when Compulsion debuted as a film, claiming that the parties had illegally appropriated his name, likeness and life story. Levin countered that the book was a roman a clef and that the names had been changed. But Leopold’s lawyer Gertz proved that the ad campaigns for the book and film relied heavily on Nathan Leopold’s name. Leopold won a million dollar verdict. But the decision was later reversed when it was decided that a criminal as notorious as Leopold could not deny being a public figure, open to fictionalization. He never made a dime from it.

Compulsion, it turns out, was not the only novel based on the case. In 1957 Mary-Carter Roberts wrote Little Brother Fate (Farrar, Straus & Cudahy) which uses the Leopold and Loeb case as part of a tripartite retelling of three famous 20s crimes. The other two being the Snyder-Gray case, used by James M. Cain in Double Indemnity (Raymond Chandler wrote the screenplay) and the notorious Halls-Mills “Lover’s Lane” case which remains unsolved. Roberts’ take on Leopold and Loeb is more about the strange hold one boy had over the other, and less about the killing. Anthony Boucher of the Times called it “vivid and penetrating,” a portrait of “larger-than-life characters…in all their torment.” He included it in his list of best books of the year.

Another novel that year also examined the case: James Yaffe’s Nothing but the Night (Little Brown). Siegfred Mandel in the Times stated that it was more tightly written and neatly plotted than Compulsion with more stress on the guilt of the parents, but that it “avoids the homosexual tie.” This is odd considering the Bantam paperback version blatantly used gay pulp style cover art to market it, and talked of “abnormal passions.” Yaffe himself said: “My object was to do a novel which would give the feeling that the boys were not obviously different from any other boys, that the same thing would happen to anybody…I give the reader the feeling that these were his boys.”

The effect of three books coming out within one year inspired some soul-searching. Rabbi Newman placed an ad in the Times promoting “Criminal Responsibility,” a sermon he was giving at Rodelph Sholom on the novels by Yaffe and Levin. Nothing But the Night was optioned to be made into a film. Bernice Block, who had produced Dino with Sal Mineo for TV’s Studio One, bought the screen rights and announced that she had contacted Elia Kazan as a possible choice for director. Perhaps she had Sal Mineo in mind for the lead. But alas nothing came of it. It would have been fascinating to see Mineo tackle the part of Nathan Leopold.

In 1964 Don Murray, below, the handsome star of Bus Stop, announced that he had optioned Life Plus 99 Years and was going to produce and star in a film based on Nathan Leopold’s life. It was to be directed by Paton Price (who later directed episodes of Surfside 6 and the Partridge Family). Murray actually went to visit Nathan Leopold in Puerto Rico. But sadly nothing came of it either.

Long before any of these versions appeared, however, the story of Leopold and Loeb inspired a play by Patrick Hamilton in 1929 called Rope. Hamilton set the tale in Mayfair, London, England, rather than Chicago, giving it more of an aristocratic edge. It was produced at the Strand in 1929. Lee Shubert produced it later on Broadway at the Theatre Masque and the Maxine Elliott Theatre. Renamed Rope’s End, it starred Ernest Melton as Rupert Cadell; Ivan Brandt as Charles Granillo, and Sebastian Shaw as Wyndham Brandon. Reginald Denham directed. The BBC made two TV versions of it: one in 1939; the other in 1950.

Few would remember it today if Alfred Hitchcock hadn’t directed a film version of it in 1948 called Rope starring James Stewart, Farley Granger and John Dall. Arthur Laurents and Hume Cronyn adapted it for the screen. In both the play and the movie, the focus is on how two sensually corrupt and spoiled youths (less explicitly homosexual in the stage version) plot to commit the perfect murder. They kill a friend of theirs, stuff his body in a trunk, then throw a cocktail party for him, inviting his family. They are outsmarted by their mentor, a Nietzschean professor, who is appalled that they took his dark philosophical musings to an illogical extreme.

The film is not one of Hitchcock’s most popular, despite excellent performances from Granger and Dall, above, and an experimental approach that involved very long takes. The problem is that James Stewart is miscast as the glib professor who misleads his protegees. If James Mason or Claude Rains had played the part, it would have been a classic. Cary Grant, alas, turned it down. Today it is a field day for queer studies theorists who see endless layers of homoerotic subtext in its campy dialogue. Indeed, I’ve often wondered if Arthur Laurents was aware of the double-entendre in the title since “rope” like “pearl necklace” is gay slang for semen. Ironically the film was criticized by the Anti-Defamation League for portraying two Jews as homosexual murderers although neither character is described as Jewish and neither of the actors was.

I have my own peculiar connection to the Leopold and Loeb case. My mother’s guardian, Elmer Gertz, above, had been the lawyer who helped Nathan Leopold finally get parole after being in prison for over 30 years. It wasn’t until after my mother died in 1993 that I finally got to meet Mr. Gertz and talk to him specifically about the case. He told me a lot of interesting things, most of which has been fully documented in his two books of memoirs. When I asked him directly about the rumors of Leopold and Loeb’s being lovers he told me a funny story. He had gone to stay with Leopold and was shocked to find that in his bedroom he kept a photograph of Elmer Gertz, and beside that, one of Richard Loeb. Leopold said they were the two most important men in his life. After Leopold got married in Puerto Rico to the widow of a local doctor, he took the picture of Dickie Loeb down.

I asked Gertz if he had seen the film Swoon by Tom Kalin (1992) which had just come out. He said he had and that he liked it which surprised me since he was a man in his late-80s at the time. Swoon takes the Leopold and Loeb case to a completely different level, offering a post-modern spin on the crime. The homoerotic relationship is made the central theme. With striking photography, anachronistic props (including a TV and touch-tone telephone) and a minimum of period costumes, Swoon breathed new life into a story that by the 90s was becoming routine. The film reawakened interest in the affair and since then there have been a number of plays and films and even graphic novels that touch upon the trial. The film Murder by Numbers, by Barbet Shroeder, is said to be based on the case, although the story line diverges in many directions.

In 1985 John Logan wrote a play called Never the Sinner which was inspired by the actual court transcripts. It won the Outer Circle Critics award and has been revived many times (above). A play version of Rope has been revived, relying on the film script as much as Hamilton’s original.

In 2003 Stephen Dolginoff premiered his musical Thrill Me: The Leopold and Loeb Story. It’s appeared in many productions around the world. In 1999, Kevin Spacey’s Darrow in the series Haunted History recreated parts of the famous trial with Jamie Harrold and Barry Del Sherman as Leopold and Loeb.

One of the most interesting tidbits I gleaned from Simon Baatz’s new book is that F. Scott Fitzgerald told a newspaper reporter from the New York World in 1927 over lunch at the Plaza (no doubt a wet lunch) that he was writing a novel based on the story of Leopold and Loeb. One can only imagine what might have been. Coming on the heels of The Great Gatsby, a novel by Fitzgerald on the “crime of the century” might just have been “the great American novel” we’ve all lusted for, a serious rival to Dreiser’s classic An American Tragedy.

What is it about these two monsters that still calls to us after 85 years? Throughout that time, the boys’ names have become synonymous with juvenile delinquency — a phrase that is almost quaint in its antiquated naivete since today no one is surprised when a child or teenager commits a crime. But back in 1924, the world was shocked by what these “juvies” had done (Loeb was only 18; Leopold a mere 19), but even more so by what they had set out to do. For their intention was to commit “the perfect murder.” To plan such a brutal killing, including kidnapping and extortion, defied logic and reason, and undercut the normal bonds of society. Their crime was beyond comprehension, sickening in its implications. And yet, despite all its evil overtones, it still thrills us to the bone.

The final twist in my recent flirtation with James Dean revolves around a grim episode in American history. It serves as a potent counterpart to our fascination with juvenile delinquents, which Dean epitomized. His allure lies also in the flip side of fame. His rebel without a cause was a two-edged sword. On one hand, he represented to us freedom. On the other, chaos and anarchy. His pain was our pain; we felt it. All of us. Whether we were good or bad, solid citizen or reprobate. He represented the misfit in us all.

While searching for images of James Dean for my earlier post (October 5th), I stumbled across pictures of Martin Sheen from the film Badlands. The movie was known to me, of course, but for some reason I had never seen it. I ordered it from Netflix. Badlands, directed by Terrence Malick, tells the tale of a handsome young garbage man, Kit, who suddenly goes on a killing rampage, taking with him his young teenage girlfriend, Holly, played with frightening froideur by Sissy Spacek.

Sheen’s character sees himself as a James Dean clone; even his girlfriend comments on his resemblance to the movie star on several occasions. Malick, (with Sheen, above) in directing the flick, underscores the comparison by having Sheen pose in certain stances reminiscent of Dean’s work in Rebel, Giant and East of Eden. The cinematography in Badlands is simply breathtaking, and the new restored DVD version shows it off in wrenchingly beautiful, vivid colors.

Even without the Dean likeness, Sheen’s performance in Badlands is mesmerizing. I only knew bits and pieces of Martin Sheen’s career, mostly from his work in Apocalypse Now (1979) and in an earlier, terrifying Outer Limits episode “Nightmare” (below) in which he plays a soldier sent to another planet, where he is brutally interrogated by sadistic aliens.

And of course I adored him in the ground-breaking 1972 TV movie That Certain Summer (which you can now enjoy in full on YouTube). Sheen also shone in a very early role in the 1967 cult classic The Incident, in which he played another Deanesque bad boy who terrorizes strap-hangers on a subway car. To see Sheen in Badlands is to glimpse what might have been if Dean had lived. But it was not to be. Even then, in the 70s, Sheen was already in his thirties, which might explain why he soon abandoned such roles. It was left to his two boys, Charlie Sheen and Emilio Estevez, to try and recapture that swagger and élan (to less than stellar effect).

Badlands, as any film or crime aficionado knows, was based on the true story of the first “spree killer,” Charlie Starkweather, who rampaged through Nebraska and Wyoming in 1958, killing eleven people for no better reason than he seemed to enjoy it. He started out by brutally killing his girlfriend’s mother and father and her two-year-old sister. The sadistic nature of how he killed them has haunted authors, law enforcement officers, and psychiatrists for years. Starkweather, whose grim name summed up his dark appeal, represented a new breed of slayer at the height of the juvie craze. He was ruthless, rapacious and totally callous. His blood lust is only hinted at in Badlands. (There’s a scene in the film in which Sheen lets two victims go free. In real life, Starkweather slaughtered them.)

Starkweather inflicted gruesome injuries on some of his victims after they were dead, sodomizing one victim with a knife. His 14-year-old girlfriend, Caril Ann Fugate, always claimed she was held hostage and had no part in the killings, although Starkweather later implicated her, calling her “trigger happy.” She was given a life sentence and was paroled in 1976. Starkweather, in a true example of swift justice, was electrocuted a year after his arrest. (From LIFE, below.)

Since his death, there has been a rash of books and films based on his life and his legendary rampage. I was surprised in researching him, just how well-known he really is. For some reason, his saga had slipped through the cracks of my consciousness. That might be because he was classified as a “spree killer,” rather than as a serial killer. But judging by the extent and cruelty of his crimes, the semantics seems rather pointless.

Some books claim that he was a social outcast who sought revenge against the world for having mocked him as a child. He had struggled with a birth defect that left him a cripple and he suffered from a severe speech impediment. Kids in school teased him mercilessly. Others looked at his stern upbringing or his job as a garbage collector for some understanding of why he went off. But despite dozens of doctors and experts analyzing the case, there has never been a satisfactory explanation. His case, like that of the two boys in Capote’s In Cold Blood, famous for the Clutter killings, can never be easily categorized. Such acts of violence and mayhem are beyond comprehension.

But the story lives on. Charles Starkweather, who fancied himself as James Dean, mimicking his pompadour, jeans, and leather jacket, and who was obsessed with the young star’s films, has become a cult figure himself, an icon of shame and horror. The first film to depict his story was The Sadist, a 1963 low-budget thriller starring Arch Hall, Jr. and a bevy of B-movie actors.

Hall, who was known for drive-in-style movies (most of which were directed by his father) gives a warped, ferociously over-the-top performance as Starkweather. It’s like watching a polished Twilight Zone episode in which one of Ed Wood’s stars suddenly appears, having stumbled in from the set of Jailbait. Yet, despite the hilarity of his bad acting and relentless grimacing, Hall’s sadistic menace works on many levels. It is a harrowing film, one of the first played out over real time, and made even more memorable by its very fine cinematography. It was Vilmos Zsgimond’s first feature.

Badlands followed in 1973. The obscure film Stark Raving Mad from 1983 was based on the case. Television did a version in 1993 called Murder in the Heartland with Tim Roth. Then in 1994 Oliver Stone took a stab at the story in Natural Born Killers with Woody Harrelson, below. Stone opened it up and gave it a madcap, nihilistic edge. Most people I know prefer Badlands. In 2004, a cheap indie appeared called Starkweather, that, judging by comments on IMDB’s forums, is one of the worst movies ever made.

What is my interest in all this? That’s a good question and I’m not sure I know the answer myself. It has something to do with why we like James Dean. Part of America has always been drawn to anti-heroes, to rebels without a cause. We may celebrate true heroes such as Daniel Boone, John Brown, or Audie Murphy in books, plays and film. But we fall in lust with our anti-heroes in a way that strikes me as uniquely American. Whether it’s John Dillinger, Scarface Capone, Freddie Krueger, the Sopranos or the Zodiac Killer, we flock to these evil-doers. It’s part of what makes us the greatest superpower on the planet, but also the place with the most serial killers and spree killers in the world.

The American Dream is also a nightmare. And while we may turn away in disgust from the actions of these so-called monsters, the crazies, we also turn back to get a closer look. James Dean, in his own peculiar, tortured way, reflected this duality. He inspired us, both the good and the bad — the Martin Sheens who strive to help save this planet and the Charles Starkweathers who yearn to bring it down.

Every now and then, when I least expect it, I will stumble across a name that for some reason begins to pop up repeatedly, almost uncannily, in the books I’m reading at that moment. Very often it’s a name I am unfamiliar with up until then. Then suddenly there’s no escaping it! Such an occurrence has just happened to me with Emily Vanderbilt, a beautiful and sometimes scandalous figure who crops up in works by or about Thomas Wolfe, E. E. Cummings, F. Scott and Zelda Fitzgerald, Edmund Wilson, Mercedes de Acosta, Dolly Wilde and Dashiell Hammett, all of which I’ve been dipping my nose into recently. It’s almost as if the hand of fate were poking a finger at me, demanding that I take notice. Well, I have taken notice. Emily Vanderbilt is a fascinating and bewildering creature, an enigma who epitomizes the highs and lows of what Gertrude Stein dubbed “the Lost Generation.” (Emily, above and below, by Arnold Genthe.)

During her glamorous, yet often troubled life, Emily Vanderbilt in fact had many names. Her birth name was Emily O’Neill Davies. She was the daughter of Frederick Martin Davies, a New York banker, broker and noted horseman, who raised his family in a large private house at 20 E. 82nd Street. Her mother, also named Emily O’Neill Davies, was the daughter of Daniel O’Neill, the editor and owner of the Pittsburgh Dispatch. When Daniel O’Neill died in 1877, leaving a fortune valued at $8,000,000, his wife Emma (nee Seely) married his brother, Eugene M. O’Neill, who took over the paper. Some reports describe Emily Vanderbilt as the granddaughter of Eugene O’Neill, but she was not. An 1880 census clearly states that her mother was the “stepdaughter” of Eugene. (Not to be confused with the famous playwright of the same name.)

The Frederick Martin Davies family lived in high style at their posh Manhattan manse. In the 1910 census they are shown to have had ten servants: a parlor maid, waitress, cook, kitchen maid, two chambermaids, two nurses, a laundress and a lady’s maid. Young Emily grew up in a rarefied world of wealth and privilege, summering in Southampton, wintering in Palm Beach, weekending in Newport, and gallivanting as a debutante among the glitterati in Manhattan’s upper crust. It was a life of extreme luxury at the height of the gilded age.

Frederick Martin Davies was the cousin of Bradley and Townsend Martin, and best friend of Alfred Gwynne Vanderbilt. Ironically, Davies died the day before Vanderbilt set sail on the ill-fated Lusitania and lost his life. So it seemed a fitting twist of fate that in a fairy-tale wedding at Grace Church in Manhattan in 1923, Davies’ beautiful young daughter Emily would marry Vanderbilt’s son, William Henry Vanderbilt III (below).

That marriage seemed, at least in the society-mad press, to be a storybook romance. But it did not fare well. They moved to Boston and Oakland Farm in Portsmouth, near Newport, which Vanderbilt had inherited in his father’s will along with $5,000,000. A daughter also named Emily was born in 1924. Three years later, William and Emily split up in a divorce that took only six minutes in court to implement. Emily claimed William had failed to provide. He was rumored to be cruel and over-protective. Some have speculated that he hired detectives to follow his wife who may have been having an affair with a handsome young theatre producer named Sigourney Thayer. In the end, Vanderbilt was granted custody of the child, permitting Emily to see her daughter only three months out of the year. William Vanderbilt III later married Anne Colby, started a bus company in Newport, then went on to become a State Senator, and ultimately Governor of Rhode Island. He died in 1981.

On December 7, 1928, Emily wed Sigourney Thayer (above). An Amherst grad, Thayer was a curious figure in New York circles. His father was William Greenough Thayer, headmaster of St. Mark’s, a tony New England prep school. When they wed, Time quipped that he was a “spasmodic theatrical producer, wartime aviator, Atlantic Monthly poet, socially prominent jokesmith.” Thayer dressed like a dandy and had a showy Proustian mustache. The marriage was a surprise to friends who didn’t think she took the affair that seriously, but perhaps she felt that it would be too big a loss to give up her daughter for a mere youthful indiscretion. She gave legitimacy to the relationship, but the marriage didn’t last. Both agreed it was a mistake. They divorced a year later.

(Above: Aline Bernstein; E. E. Cummings; Thomas Wolfe; Edmund Wilson)

Emily Vanderbilt Thayer led a gay social life in Paris and was a fixture in literary circles. She aspired to be a writer and critic, and surrounded herself with well-known authors. She knew Gertrude Stein and Alice B. Toklas, and became chummy with dancers from the Ballets Russes. At a party hosted by Muriel Draper, she first encountered E. E. Cummings. He found her, according to one source, “blonde, statuesque, charming and gorgeous.” They had a two-month affair. She soon fell for Thomas Wolfe whom she met through Aline Bernstein. Emily “tried to make him,” according to F. Scott Fitzgerald, who followed her comings and goings with a fascinated eye. She would write Wolfe urgent notes written in a childish scrawl, begging to see him. Wolfe reportedly was astonished by her beauty and seductive charms, but was wary of her insolence and sexually aggressive ways. He found her “fundamentally trivial.” Wolfe’s biographer David H. Donald says he was “disgusted by her systematic and rather dogged experience of the life of degeneracy and refused to join her in smoking opium.” He detested her gigolo Raymonde, “a bad Valentino.” Worse, she paraded Wolfe among her friends as someone “madly in love with her.” He fled to Rouen. Wolfe eventually used Emily as the basis of the character Amy Carlton in his novel You Can’t Go Home Again. Fitzgerald praised his description of her “cracked grey eyes,” and “exactly reproduced speech,” as “simply perfect.”

Emily didn’t limit her affairs to male writers. She was drawn to the lesbian demimonde, dominated by Natalie Barney and Djuna Barnes. According to Zelda Fitzgerald biographer Sally Cline, Emily was most likely bisexual. She was close friends with Dolly Wilde, the notorious niece of Oscar Wilde, as well as Mercedes de Acosta, another social butterfly who achieved fame by her dalliances with great writers and movie stars.  I found a ship record for the two of them traveling together aboard the Olympic from France to New York in 1929. On it, Emily gave her birthday as August 10, 1903. Mercedes claimed to be 30, born in 1899, although she was actually six years older. At the time Emily maintained a home at 176 E. 75th St.

(Above: Djuna Barnes and Natalie Barney; Zelda Fitzgerald; Mercedes de Acosta; Dolly Wilde)

During this period, as the Jazz Age reached a fever pitch before the inevitable plunge, Emily was swept up in the decadence of cafe society, flouncing around with a bunch of Hemingwayesque expatriate socialites who’d come to live it up in Europe. Zelda Fitzgerald said that she “was sorry for her. She seemed so muddled and lost in the grist mill.” Scott, hoping to bolster Zelda’s spirits, who was jealous of Emily’s sophisticated allure, dismissed her in a letter as someone who “could not dance a Brahms waltz, or write a story. She can only gossip and ride in the Bois and have pretty hair curling up instead of thinking.” Scott may have been projecting his own sense of insecurity among the very rich. Thomas Wolfe considered him a social climber. Fitzgerald, despite his misgivings about her, had an affair with Emily in 1930, when Zelda was in Prangins recovering from a breakdown. But it didn’t amount to much. Fitzgerald later wrote that she “was too big a poisson for me.” He remained mesmerized by her, however. Both he and Zelda kept clippings about her in their scrapbooks.

Emily in fact did have higher dreams than just being a transatlantic party girl. She wrote books and articles but never tried to get them published. Asked if she would ever write for publication, she coyly answered: “I will tell you in twenty years.” In 1929 it was announced with fanfare that she would become a reader for the publishing firm Boni & Liveright (one of the foremost houses in publishing at that time). Its founder Horace Liveright was a bon vivant and ladies man who managed to lure the leading lights of the literary firmament to his doors. Eugene O’Neill, T. S. Eliot, Ernest Hemingway and Theodore Dreiser were all published by him. Emily relished her role as reader and used her contacts to aid Liveright. Lillian Hellman first took note of Emily Vanderbilt at the 1934 opening night party of her first play, The Children’s Hour, which was about a lesbian scandal in a girl’s school. Hellman described her as a “a handsome, boyish-looking woman” seen at every literary cocktail party. Judging by photos of Emily taken by Carl Van Vechten in this period (below), she was still striking looking, but perhaps not as innocently radiant as before.

Emily’s interest in literature was serious and well-informed. It might explain her marriage in 1933 to the writer Raoul Whitfield. One of the big names at Black Mask magazine, a pulp that published Dashiell Hammett and Raymond Chandler and defined the “hard-boiled” genre, Whitfield was a former aviator who fought in World War One and claimed to have won the Croix de Guerre for distinguished service, although some critics have suggested that such an honor was more likely a “flight of imagination.” One biographer described him as sporting a “cane, elegant leather gloves and a silk scarf around his neck, looking aloof and imperious. His mustache is carefully trimmed, his dark hair slicked back and parted in the middle. Every inch the gentleman.” (Below, Raoul Whitfield from Argosy).

Whitfield’s family traveled abroad when he was young and he was raised partly in the Philippines. His middle name was Falconia but he used the name Raoul Fauconnier Whitfield when describing himself. He was something of a mystery himself, and remains so to his most devoted fans. Throughout his life he held many odd jobs, including fire fighter in the Sierra Madre range, a bond salesman in Pittsburgh, and a newspaper reporter. He even tried his hand at acting in silent films. Widely considered one of the top detective story writers, he was a close friend of Dashiell Hammett’s. Hammett later had an intimate affair with Whitfield’s first wife Prudence Smith after the couple’s divorce.

Emily saw in Raoul a way out of her wayward existence in cafe society. She admired his writing ability and wrote a play with him called Mistral. But the marriage was tempestuous from the start. By this time she was drinking heavily and using sleeping pills at night. She became increasingly moody and difficult. Today she might be diagnosed as suffering from manic depression. Yet at first the marriage seemed successful. They bought a rambling spread in Las Vegas, New Mexico which they called “Dead Horse Ranch.” Here they raised cattle, built a polo field, a golf course and entertained friends from both coasts on a lavish scale. But the union soon devolved into jealous rages and accusations of infidelity. Raoul was allegedly having an affair with a local barmaid named Lois Bell.

The final chapter in Emily’s life reads like the climax of one of Whitfield’s violent novels. Shortly after starting divorce action against Whitfield, Emily was found shot to death in her bedroom at the ranch on May 24, 1935. A hastily assembled coroner’s jury found that she had committed suicide, despite the fact that the gunshot wound was on her lower left side and she was right-handed. The bullet, from a Colt .45, passed through her lungs and hit her heart. The New York Times reported that she had become “despondent after a conference yesterday on a divorce suit.” Her friend Mrs. Virginia Haydon Stone was with her earlier but did not spend the night. Emily retired at 11 PM. “The body, clothed in pajamas and a dressing robe, was found at 7:30 o’clock [the next] morning, on the bed, a revolver clutched in the outflung right hand.” The body was discovered by an employee at the ranch. But almost immediately speculation grew that someone had killed Emily Vanderbilt Whitfield. Lillian Hellman did not mince words when she wrote later: “she was murdered… and neither the mystery story expert nor the police ever found the murderer.” (Below: Lillian Hellman and Dashiell Hammett.)

Whitfield was a prime suspect, even though he had proof that he was in California at the time of Emily’s death. Some suspected he hired someone to kill her. For the rest of his life he lived under a cloud. He inherited a small fortune, then married Lois Bell and moved about constantly, almost frenetically. He went through the money like a dose of salts. Adding to the tragedy was the suicide of Lois Bell, who leaped from a hotel window in San Francisco in 1943. Raoul Whitfield’s health deteriorated. He had tuberculosis. Hammett, in a typically generous gesture, asked Hellman to send him a check for $500. Whitfield died, broke, in a military hospital on January 24, 1945.

Not surprisingly, the story of Emily Vanderbilt Thayer Whitfield has fascinated writers for 75 years. Recently a novel based on the case has been published which delves into the circumstances of her death and offers a very dramatic, yet plausible solution. Written by Walter Satterthwait, the novel is Dead Horse. I won’t give away the ending, but it is utterly convincing. You can read more about it at the author’s website: www.satterthwait.com.

As for Emily’s daughter, she was raised by her father William H. Vanderbilt. Nicknamed “Paddy,” she married Jeptha Wade, an attorney, originally from Cleveland. They lived in Boston. He died a year ago August at 83.  She is a Life Member Emeritus of the MIT Corporation, and President of MITS, Inc.

Emily O’Neill Davies Vanderbilt Thayer Whitfield may have been a character of many names, with three troubled marriages, but she was not easily categorized. As a debutante, she enchanted high society. As an heiress, she married “well” only to find that fairy-tale romances are bittersweet. As a mother, she was devoted to her daughter despite years of separation. But she was also a woman who defied the strictures of her age, became a respected devotee of the finest authors of her day, and ended as an iconoclast who lived and loved on her own terms. Whether tragic muse or literary butterfly, her legacy will haunt us for generations to come.