Jingle This: Five True-Crime Masterpieces For Your Holiday Wish List

Classics Lists Mystery Transgressive

(Once again, a word from our crime/noir genre specialist Garrett Kenyon. -- Levi)

Christmas is the perfect time for true crime. You have to deal with members of the family you only see once a year, eat dry turkey and drink poxy eggnog, and pretend to be excited about the new shirt you’ll be returning next week. All this while dealing with a gaggle of kids excited about an overweight, glorified second-story man who’ll be reverse-burglarizing your home when the lights go out.

If you’re like me, and you’d rather hear a clip full of shell casings from a silenced .22 hitting the ground than the sound of jingle bells -- these books should help get you through the holiday celebration and winter of discontent beyond. Put ‘em on your list and pass it along with a threatening stare and some egregious knuckle-cracking and soon you’ll be reading about some of the most engaging bad men and women who ever lived.

1. Herbert Asbury - The Gangs of New York (1928), The Barbary Coast (1933), The French Quarter (1936) and Gem of the Prairie (1940)

Asbury described his work best when he labeled it “an informal history of the underworld.” Each book describes the seedy underbelly of a different city (New York, San Francisco, New Orleans and Chicago, respectively) from the 19th to the early 20th century, introducing readers to the gangsters, crooked cops, lowlife politicians, cut-throat streetwalkers and punch drunk thugs who laid the foundations of what we now so euphemistically call “the game.” And while their various schemes might seem passé compared to today’s high-tech criminals, the old-timey villains had a certain panache that today’s average skell could never muster. Asbury records all the lurid details in the purple-prose style that was so popular at the time, making either four of these books a damned fun read.

I recommend starting with Gangs of New York*. Asbury acts as a genial guide, leading you confidently into notorious slums like the Bowery and Five Points, where you’ll pass through Murderer’s Alley for a tour of the Old Brewery, a den of vice and depravity unequaled in American history; spend time in blind pigs and dancehalls with names like The Bucket of Blood and McGurk’s Suicide Hall; and meet men like Monk Eastman, Bill the Butcher, Baboon Connolly and a couple hundred more colorfully-named thugs who’ll make the bubble-coated gangsters currently hanging out on your block look like powdery-bottomed prep-school boys.

*Which has very little to do with Scorsese’s film.

2. Jack Black - You Can’t Win (1926)

This little-known book gets my enthusiastic vote for the best autobiography ever. It’s the story of introspective hobo and itinerant lowlife Jack Black, who falls in with some old school bindle stiffs as a boy and spends the rest of his life riding trains back and forth across Gilded Age America. On his travels, Jack robs general stores, jewelry shops and post offices, gets broken out of jail at least three times, becomes addicted to, and then kicks, opium in a Canadian boardinghouse, has run-ins with killers, whores, thieves, fences and cowboys and even Wild West legends like Bat Masterson and Judge Fremont Older. The story is told with a wry, self-deprecating voice that leads you seamlessly from one adventure to the next as Jack grows from a scared runaway to a veteran member of the Johnson family*, mastering the art of survival-by-wit. You Can’t Win was a particular favorite of the Beats. Recent editions feature a foreword by William S. Burroughs, who explains how important this book was as a blueprint for their literature. I recommend You Can’t Win for anyone who can read. It not only offers a glimpse of a post-Civil War America left out of the history books, but it gives you tons of old-timey one-liners like “I’m so broke – if it was raining soup I couldn’t afford a tin spoon!” And who can’t use a few more lines like that in their arsenal?

*Read the book.

3. Edward Bunker - Education of a Felon: A Memoir (2000)

If you still haven’t read Bunker, you’re in for a treat. America’s premier prison writer, Bunker has perfected giving guided tours of the criminal mind. When he leads you inside the dolorous grey walls of the big house, he makes you feel the razor-sharp paranoia that comes from being surrounded by thousands of violent men, all fighting to be king of the jungle. Bunker never reached the level of appreciation he deserved in the States – but the Europeans saw him for what he was – a world-class writer who also happened to be a habitual criminal. In Education we get to see just how he got that way – and what a story it is. Rarely does Golden Era Hollywood come to life in such glorious detail – at least not the grimy side left off the glossy brochures. Try reading this book and not going online immediately to find out the rest of what happened to Bunker – it’s almost impossible.

4. Jay Robert Nash - Bloodletters and Badmen (1972 with revised editions in '92 and '95)

The ultimate encyclopedia of low-down scoundrels. Chronicling America’s villains “from pilgrims to present”, Bloodletters has enough gangsters, serial killers, bank robbers, hitmen, vigilantes, confidence men, black widows, mass murderers and gun slingers to satisfy any outlaw enthusiast. But it’s not the baddies that set this encyclopedia above the rest – it’s the writing. The passages are witty, concise and informative, and Nash has a sharp eye for those little details that bring a story to life. I’ve lost many nights to this book – picking it up in the evening to read a few passages, and not stopping until the birds are chirping and my eyes bleary. One of the best features of Bloodletters is how, at the end of each bad guy’s story, Nash lists the other criminals they crossed paths with during their career. Since the passages are so well written, you feel compelled to go on and read the bios of those criminals. This way, it’s possible to work your way up from the Old West black hats, through the 20’s and 30’s Tommy-gun-toting fedoras and into the crazy-eyed 70’s long-hairs, following an unbroken trail of blood and bad influence from past to present. Bloodletters and Badmen is a crown jewel in any crime lover’s collection.

5. Jeff Guinn - Go Down Together (2008)

If you’re like me, you have a soft spot for the golden-age gangsters – men like Pretty Boy Floyd and John Dillinger, Baby Face Nelson and Machine Gun Kelly, who terrorized Depression-era lawmen and became national heroes for an entire generation of beat-down Americans. But perhaps no characters from the Public Enemy era have garnered as much fascination as Bonnie and Clyde – doomed lovers blazing a one-way path to hell across the Southern States and into the history books. Guinn does an admirable job of looking beyond the legend and making Bonnie and Clyde real people again. Despite the current fashionable view on Bonnie and Clyde (that they were a couple of bloodthirsty, lowlife amateurs), there is a humanity and honor about them that is undeniable. Bonnie was a self-conscious drama queen who fancied herself a poet and preferred to be the center of attention ... but when she had a valid reason to leave Clyde behind (her leg had been literally burnt to a crisp in an automobile accident), she chose to stay with her man until the bitter end they both knew would come shortly. Clyde risked everything to break a man out of jail that he particularly disliked; not because it would get him anything – but because the man had been convicted of a crime he didn’t commit and it was the right thing to do. While they weren’t nearly as talented as Pretty Boy or as charismatic as Dillinger, Bonnie and Clyde earned their legend with blood, tears and bullets. Not a bad couple to spend a few days with.

The 5 Other True-Crime Titles I Would Have Added if I Weren’t So Lazy

Lowlife by Luc Sante
The Corner or Homicide by David Simon
American Brutus by Michael Kauffman
The Complete Jack the Ripper by Donald Rumbelow
Devil in the White City: Murder, Magic and Madness at the Fair that Changed the World by Erik Larson

18 Responses to "Jingle This: Five True-Crime Masterpieces For Your Holiday Wish List"

by Ziggy on

Uh - could you tell me something about a banner ad that promoted a book that actually sounds interesting? I think it was, "What is Your Poo Telling You?"

by Ann on

Nice list! i was looking for book for my brother who likes nonfiction about crime. i have a question that might sound stupid but are there any Christian crime books? hes a bornagain. if not I think Ill get him that jack black book (thought it was the comedian at first!LOL). Thanks for doing this for all us who arent crime/noir specialists!

by Levi Asher on

Ziggy, I think you're referring to a blog ad on the site -- why not click through and find out? I have no idea what anybody's "poo" is telling them, but apparently the author of this book does.

BTW, in case anyone's wondering, the photo above is one of Jacob Riis's classics taken in the Gangs of New York-era Five Points.

Ann, hopefully Garrett can answer your question about Christian crime books.

Garrett, you make all these sound great! Hard decision which one to read first, but I'll probably go with You Can't Win, just because William Burroughs talked about it.

I'm sorely tempted to say a born again true crime book would be an Oral Roberts biogrpahy, but I really don't want to offend anyone and I have good friends and family members who would chastise me for such a statement.

by Garrett on

Thanks Bill. Ann -- I'm sorry, I don't think I'm going to be able to help you out with a true crime/crime fiction book that's written specifically for Christians. Not really my cup of tea. There are, however, some popular detective series with Christian protagonists. Inspector Rebus from Ian Rankin's books is a Catholic. Ken Bruen, one of my favorite writers, has an excellent series about a guy named Jack Taylor (see my previous post). Jack is a lapsed Catholic, but a lot of his cases involve the church -- though I've got to warn you that the church doesn't exactly come out smelling like roses. That's about all I can think of right now.

And Ziggy -- I don't mind someone putting a completely unrelated comment after one of my posts -- but did it really have to be the first one?

by Rafo on

Thank you for the summary about "Jack Black - You Can’t Win (1926)"...I can see it will be in my "To be read" queue along other books I have been targeting.

by Jennifer H on

Absolutely fascinating list! I haven't read any of the books listed but all sound like a wonderful place to get lost while the extended family is busy gorging on food and getting into spats over meaningless stuff.

As for the 5 other books listed in the P.S., I couldn't have enjoyed "Devil in a White City" any more if I tried. I would, however, add Ann Rule's "The Stranger Beside Me" for an intriguing insight into the serial killer's mind (all of her other books are mediocre, IMHO, but this one's stunning).

Great list - thanks!

by Rochelle Walsh on

Nice list.... I'm not a fan of the crime/genre, but have brother who is, so this should help me pick out something he'll like. Thanks

by Swifty on

Hey man, nice list. Loved the part where you compared jingle bells to the sound of .22 shells hitting the ground. Classic. You should do more crime stuff here. Wondering why you didn't mention Helter Skelter here, or something by Jimmy Breslin? Keep 'em coming.

You must add THE ROAD OUT OF HELL: SANFORD CLARK AND THE TRUE STORY OF THE WINEVILLE MURDERS by Anthony Flacco. Just came out last month and reviews are incredible. See book trailer at www.AnthonyFlacco.com

by Ann on

Thanks for responding to my comment. As it turns out, I asked my OTHER brother, and he says a christian crime book (if any exist) would be a bad idea anyway. Now I have another quesiton:

You mention the book about Bonnie and Clyde, but could you recommend any books about Jon Dillinger or any of the other big time gangsters from that era? I saw Public Enemies recently and it made me want to read about some of those famous outlaws.

by Garrett on

Sorry for my slow response here -- I've been "unplugged" for a few days. I'll tell you, Swifty, if that is your real name...(irony intended), I didn't mention Breslin or Helter Skelter's Bugliosi for pretty much the same reason: in my humble opinion, both of those guys are journalists who don't necessarily excel at writing books. Now in the circles I run in -- that statement could earn me a shiv between the shoulder blades -- and I have nothing but respect for Jimmy Breslin...the journalist...but anyone who read his last book, "The Good Rat" can tell you that it is extremely hard to follow. Bugliosi's book is similar -- here he has one of the juciest subjects in the history of crime writing -- crazy-eyed Charlie Manson, a bunch of sex-crazed, thrill-killing hippie chicks, Roman Polanski's wife Sharon Tate....and somehow he manages to write one of the most dry, monotone books I've ever read. Robert Graysmith did the same thing with "Zodiak" -- another to-die-for subject turned into one mess of a book. Okay, that ought to rate me a few hard-earned hate-letters, let's move on to...

Question #2:
Ann, there's plenty of great books on the Depression era bank robbers -- both fiction and non. For Dillinger, "Public Enemies" was pretty good -- but for a more entertaining read, try "John Dillinger: The Life and Death of America's First Celebrity Criminal" by Dary Matera. Finally, Larry McMurtry, a big western writer wrote a novel called "Pretty Boy Floyd" that not only sticks very closely to the facts of Charlie Floyd's life -- but is one hell of a great read. Hope that helps.

by Big L on

Hey man, I just wanted to say thanks for this list. I’ve been wanting to get into crime for ahwile but there’s so much out there it’s hard to know where to start. I was looking for some holiday reading and came across your list few days ago. I love the way you described the books, you made them ALL sound good. I went to Half Price that night and picked up You Can’t Win and Bloodletters and Badmen. I finished reading You Can’t Win tonight and just had to write you to say “thanks”. Jack Black is the OG! I was up til 4:30 reading last night and my wife kept asking me to come to bed, but I was just hooked, man! . Keep up the good work and keep those suggestions coming.

One last thing: any chance you could do a list of black mystery writers soon? That would be most appreciated.

by mike on

Wish my mother was still alive this was her thing. I'd print it out for her and let her pick of them.

by Kathy Brooke on

You left out two excellent books: In Cold Blood by Truman Capote and Executioner's Song by Norman Mailer.

by Drew Hunkins on

Another good one that sort of fits this list is the autobiography of legendary sax man Art Pepper. It's called 'Straight Life' and documents his life of petty crime supporting his heroin addiction more so than his music career. One of the best autobiographies ever written.

by G. Kenyon on

Aaaah...therein lies the problem with writing any "list" -- you inevitably have to leave out books you'd like to include. "In Cold Blood" is, of course, a giant of the genre, and I figured everyone would have heard of that. Mailer's "Executioner's Song" was also brilliant. I avoided reading it for years, thinking "how could he possibly keep me interested for 1,000+ pages about such a minor criminal as Gary Gilmore?" But Mailer pulls it off.

I can think of at least 2 dozen others I'd have liked to list -- but I wanted to include my personal favorite (You Can't Win), a genre classic (Gangs of NY), something very recent (Go Down Together), something from the criminal's perspective (Education of a Felon) and one of those true-crime encyclopedia's that have brought me so many nights of pleasure -- of which "Bloodletters and Badmen" is most certainly the best. And to the last commenter -- "Straight Life" has just been added to my "Definite Pick-Up list." Thanks.

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