There comes a time in every crime writer’s life when they have to construct their very own crime boss. But what qualities do you want to invest in your make-believe mobster? Are they charming and comical, or sinister and serious? And what kind of outfit do they run, a gang or a crew? And where are they in their criminal journey, an up-and-coming, streetwise soldier or a rich and powerful kingpin at the top of the criminal food chain?
These were the questions I grappled with when I set out to develop my very own don in my latest novel. In Dirty 20, Tommy Fugue is the son of Denver crime lord Alessandro “Big Al” Fugue. Tommy wants nothing to do with the family business, only to go to college, but his father assigns him a “summer job” of laundering money online. Tommy creates a fake roleplaying game on FunFunder, pledges it with zombie accounts, and figures he’s home free…until the game goes viral. Now Big Al smells money…and blood.
Balancing my mafioso’s magnetic charm with a palpable sense of menace was tricky, but I took some cues from my favorite hoods. Below are my personal Top Five fictional crime bosses, and in keeping with Tommy’s roleplaying game, I included which of their “stats” helped to inspire Big Al Fugue.
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Walton Goggins as Boyd Crowder in Justified
Number Five
Boyd Crowder
This Kentucky criminal with a penchant for smooth talk and blowing stuff up was supposed to die in the pilot episode of Justified, but such was the live wire loquaciousness of Walton Goggins as well as his chemistry with straight-shooting U.S. Marshall Raylan Givens that he became the hero’s foil for the show’s entire six season run. Boyd dabbled in every crime in the holler and was at war with fellow crooks as much as with the feds, playing all the angles and usually talking his way out of trouble with his silver tongue.
I’ll give Boyd himself the last word: “I’ve been accused of being a lot of things. Inarticulate ain’t one of them.”
- Ability: Charisma
- Skill: Persuasion
Robert de Niro as Jimmy Conway in Goodfellas
Number Four
Robert De Niro (137-way tie)
This is a double cheat, first because Robert De Niro is not a fictional character, and second because I couldn’t pick just one character. How could I?
There’s Jimmy Conway, the platonic mafia ideal of Goodfellas, my favorite movie. Then there’s Al Capone himself in The Untouchables. And don’t forget about stoic Neil McCauley from Heat. De Niro even lampooned the mobster persona he more than anyone else defined in Analyze This.
Has there even been another actor who has played gangsters as prolifically or indelibly as Bobby D? Fuhgeddaboudit. He first sauntered onto movie screens to Jumpin’ Jack Flash in 1973’s Mean Streets and he’s been stealing films ever since.
- Ability: Intelligence
- Skill: History
Vincent D’Onofrio as Wilson Fisk in Daredevil: Born Again
Number Three
The Kingpin
While Gotham City is the premier cesspool of crime in all of comics with arguably the best Rogues Gallery, don’t sleep on Daredevil’s playground, Hell’s Kitchen, or its very own Kingpin of Crime, Wilson Fisk.
Whether the Kingpin is illustrated by the legendary Bill Sienkiewicz and others on the page, or animated in Spider-Man: Into the Spider-Verse, or portrayed on-screen by the inimitable Vincent D’Onofrio, the Kingpin exudes stature. He is immense, both an immovable object and an unstoppable criminal force. Yet he has no special powers beyond his own cunning.
In addition to being bedeviled by Matt Murdock, he tussles with the other street-level superheroes of the Marvel Universe, to say nothing of rival criminal factions. He’s been toppled several times, only to come back each time stronger than ever, even being elected as mayor of New York City.
- Ability: Wisdom
- Skill: Survival
James Gandolfini as Tony Soprano in The Sopranos
Number Two
Tony Soprano
When I was younger, the benchmark for all mafia stories were The Godfather films, influencing every mob tale that came after it. Then came The Sopranos. It too referenced The Godfather films, referring to them in-show as simply “One” and “Two,” but the groundbreaking prestige drama took every preceding mob portrayal and remixed it for a new era with deep characterization and a wicked, knowing humor.
And the show could not have worked without the towering performance of James Gandolfini as the titular mob boss to anchor it. Gandolfini was so compelling to watch that we lulled ourselves into thinking Tony was a complicated antihero until he reminded us he was an affable monster. Don Corleone deserves his kisses on the ring, but for the new gold standard, it’s “T” for me.
- Ability: Charisma
- Skill: Performance
Darth Vader from Rogue One: A Star Wars Story
Number One
Darth Vader
I know what you’re thinking: Darth Vader is a Sith Lord, a former Jedi seduced by the dark side of the Force, and the Supreme Commander of the Empire. How dare you minimize him as a simple “crime boss?” Honestly, I find your lack of faith disturbing, so I’ll leave it to my very own Big Al to make the case, as he does in Dirty 20 when explaining his own reverence for the character to Tommy:
And then on the screen—with that deep James Earl Jones voice and all decked out in black head to toe—comes Darth Vader. The look. The breathing. The music… Anyway, that’s when it hit me. He’s a gangster. A stone-cold space gangster. Literally. He’s an enforcer, an underboss to the emperor. And just like that, I understood him in my bones. Even as a little kid. I was obsessed. To me, he was the show. Not Luke, not Han. Not the cute little droids. From then on, Vader waJims my guy. Until he went soft in that last one. But up until then? Baddest cat in the galaxy.
- Ability: Charisma / Strength / Constitution (Seriously, my guy got hacked to pieces and fried in a lava river and he still kicks ass).
- Skill: Intimidation
Your mileage may vary, but there’s no need for a gang war! Post your fictional favorites in the comments!
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