The Sopranos

10 Best Books About Gangsters Like The Sopranos

Fans of The Sopranos have a wide range of fiction and non-fiction reads to check out, with the same kind of fascinating look at gangster life.

The Sopranos has acquired a cult fanbase over the years with the HBO show being as popular as ever even now. While it stems from an original concept by showrunner David Chase, The Sopranos is definitely reminiscent of several other pieces of crime fiction and non-fiction.

Ranging from stories based on real-life crime figures to fictional tales of organized crime empires, these books would serve as good reads for those fans who crave to consume more stories of sin, betrayal, and a violent sense of existentialism.

Black Mass (Dick Lehr and Gerard O’Neill)

Cover of Black Mass

Popularized by the movie of the same name starring Johnny Depp, Black Mass is a non-fiction book that charters the rise of Boston mobster Whitey Bulger and his alliance with the FBI as an informant. Thrown in the mix is FBI Agent John Connolly who was Bulger’s childhood friend and helped him in warding off a rival family that posed as a threat.

Right from the early seasons, The Sopranos features FBI Agents and policemen who are allied to Tony Soprano and his criminal allies. Stories like these end up showing how law enforcement officials walk on thin ice when it comes to dealing with career criminals.

The Last Don (Mario Puzo)

Cover of The Last Don

While Mario Puzo is known for The Godfather, his other mafia-centric book are equally cinematic in scope.  The Last Don is an interesting look into the final days of an aging patriarch of a mob family and his efforts to secure a legal future for his family. Interspersed in this narrative is the Mafia’s connection with Hollywood and the casino business.

Tony Soprano’s parenting might not have aged well but he does try his best to prevent his son from walking the same path as him just like Don Domenico Clericuzio’s concerns for his children. As for the film business’ connection with gangsters, Christopher Moltisanti’s arc towards the latter seasons covers a similar theme in great detail. So, Puzo’s third-last novel is bound to impress Sopranos fans.

Wise Guy (Nicholas Pileggi)

Cover of Wise Guy by Nicholas Pileggi

The book that inspired the Martin Scorsese classic film Goodfellas is a comprehensive source of information for anyone who wishes to know more about Mafia associates and informants while focusing on the life of Henry Hill. Crime reporter Nicholas Pileggi painstakingly records Hill’s ascension to the ranks in a Mafia family and his eventual downfall.

Characters like Hill and his friends like Jimmy Burke and Tommy DeSimone would remind readers of Tony Soprano. These similarities arise not just out of their criminal backgrounds but also personality traits like anger issues and constant adultery.

The Sopranos & Philosophy (Various)

Cover of The Sopranos and Philosophy

The beauty of The Sopranos is the possibility of multiple interpretations. With enough gray areas, the characters are quite polarizing in the choices they make in life. The Sopranos and Philosophy attempts to analyze the characters through a series of essays that draw on actual philosophical readings.

RELATED: The Sopranos Characters Ranked From Least To Most Likely To Win In Squid Game

From exploring Tony Soprano’s duality to Carmela Soprano’s supposed feminism, the compilation succeeds in offering new perspectives on the characters that made the show popular in the first place. An added bonus is a foreword authored by The Sopranos cast member Vincent Pastore.

Son Of The Mob (Gordon Korman)

Cover of Son of the Mob

Vince Luca tries to lead the life of an ordinary high-schooler even though his father is a high-ranking gangster. While Luca doesn’t mind using his father’s influence every once in a while, it becomes a Herculean task to come clean to the girl he likes. What follows is a darkly comic story of teenage romance and family issues.

A clear parallel can be drawn between Luca and Anthony Junior from The Sopranos, both being characters who are trying to come out of their infamous fathers’ shadows. Son of the Mob almost feels like AJ’s story as he explores friendships, love, and his own psyche all through The Sopranos.

Road To Perdition (Max Alan Collins)

The cover of Road to Perdition by Max Allan Collins.

Road To Perdition is the story of a gangster running away from his boss and bonding with his son along the way. Even though he endangers the life of his sole child, the protagonist tries his best in being the father that he couldn’t be earlier. The tale is brought to life by comic book writer Max Allan Collin’s gripping storyline and Richard Piers Rayner’s artwork.

RELATED: 10 Comic Book Movies You Might Have Forgotten About

Even though Tony Soprano and Anthony Junior’s relationship might not be as wholesome as the father-son duo in Road To Perdition, the graphic novel covers familiar themes of violence, adolescence, and redemption.

The Family Corleone (Ed Falco)

Cover of The Family Corleone

A prequel to Mario Puzo’s iconic book The GodfatherThe Family Corleone takes inspiration from an unproduced screenplay by the late maestro. Some of the story arcs that this 2012 novel covers include Don Vito Corleone’s rise to power in New York, Sonny Corleone’s initiation into the family as well as Tom Hagen’s past.

Given the Mafia references in The Sopranos, Puzo’s bibliography makes for essential reading for the show’s fans. But for those who have missed out on books set in the “Mario Puzo universe”, The Family Corleone would be a good start.

Live By Night (Dennis Lehane)

Cover of Live By Night

A novel set in Prohibition-era America, Live By Night takes a look at the organized crime that sprung out of underground distilleries during this time. As one such gangster makes his way through the American dream, readers can also expect a diverse cast of characters including corrupt cops, Ku Klux Klan members, and Cuban revolutionaries.

RELATED: 10 Best Gangster Movies, According To The American Film Institute

Their motivations might be different but leading man Joe Coughlin’s rise to the top is reminiscent of Tony Soprano’s rise as a mob boss. Even though both start off as patient learners in the ways of crime, their ascent makes them extremely ambitious and notorious.

Five Families (Selwyn Raab)

Cover of Five Families

One of the recurring elements in American gangster movies and books is the presence of multiple families. As its title suggests, Five Families traces the history of the infamous Mafia families that turned New York crime into a powerful empire.

The Sopranos is set in New Jersey but it includes a lot of allusions to such families as multiple parties clash with Tony’s operations as a part of turf wars and commercial expansions. These civil wars between opposing factions are explored is fleshed out particularly in the final season. So, a book like Five Families would come in handy to understand the historical context behind such clashes.

I Heard You Paint Houses (Charles Brandt)

Cover of I Heard You Paint Houses

Serving as the inspiration for The IrishmanI Heard You Paint Houses documents the life of Bufalino Crime Family hitman Frank Sheeran and the crimes that he confesses to in this revealing work of nonfiction. The book also expands upon Sheeran’s friendship with trade unionist and crime associate Jim Hoffa.

According to Charles Brandt’s book, Sheeran is also alleged to have betrayed and killed Hoffa when he proved to be a liability. The buildup to this crime is bound to remind Sopranos viewers about the shocking way Tony ended up murdering Christopher.

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