For better or for worse, if you look at my bookcase or my DVD collection, a quarter of the inventory falls into the organized crime genre. I love the fast moving, hard hitting tales of crews who had enough dirty money to fix a world series and transform Las Vegas. Not to mention, the wacky nicknames that these dudes had.

When it comes to organized crime literature, its gotta be True Crime. Well there is one exception, but for the most part I like the first hand accounts of the underworld. Here are my favorite picks.

Boss of Bosses: The FBI and Paul Castellano by Joseph F. O’Brien and Andres Kurins
This book is all about Paul Castellano’s role as the boss of the Gambino Crime Family. At the time of his rule, the Gambino Family was the largest of the Five New York Families. This book not only explores the family’s underworld exploits, but it also documents the FBI’s attempts to take the Gambino Family down. This is a great book, which really breaks down the lifestyle, structure, and activities of “La Cosa Nostra”. I will have to make a pilgrimage to Spark’s Steakhouse one of these days. Hopefully my meal will end a bit better than Big Paulie’s.
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The Westies: Inside New York’s Irish Mob by T.J. English
The Westies deals with the Irish Mob in New York’s Hell’s Kitchen. The book centers on the rise of two street criminals, Jimmy Coonan and Mickey Featherstone, who would eventually run all of Hell’s Kitchen’s rackets. It is filled to the brim with dismemberment, drugs, and despicable criminals. You won’t find any big money mafiosos in here. The Westies is so gruesome, that part of me wishes that I never read it.
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Underboss: Sammy the Bull Gravano’s Story of Life in the Mafia by Peter Maas
Underboss focuses on the life of Sammy “The Bull” Gravano. He rises through the ranks of the Gambino Crime Family (under Paul Castellano from Boss of Bosses) and eventually becomes an underboss beneath John Gotti. Underboss portrays “The Bull” as a cold-blooded killer, but towards the end, I almost started feeling sorry for the guy.
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The Godfather by Mario Puzo
Now for the exception that I mentioned before. The Godfather, a work of fiction, needs to round out this list of my favorite organized crime books. It is such a captivating read and much of its foundation draws on actual mafia history. Not to mention, it is a book whose film interpretation actually does it justice.
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As for Organized Crime Movies, I think the picks are obvious. Godfather, Scarface, Goodfellas, Casino, and The Departed (an instant classic). But there is one movie which is not so well known on MTV Cribs.

Cocaine Cowboys
This documentary is all about the figures that were responsible for importing vast amounts of cocaine into the United States through Miami, FL. It is very much like Blow and Scarface…but real and without any Hollywood embellishment. Check this one out.
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