Writer’s Corner: Nicholas Pileggi’s “Wiseguy”


As far back as I can remember everyone’s acted like Goodfellas (1990) was Martin Scorsese’s best film. It’s a fair statement when you get down to pure iconography. After all, that tracking shot through the kitchen is a technical feat that only a master could pull off. Joe Pesci’s performance has this ability to get under your skin, making you think that you’re watching a crazy man about to pull a knife on you. Everything about the film has become something iconic in the world of gangster cinema, taking away the lavish tapestry of The Godfather (1972) and replacing it with scrappy American rudeness that feels like it’s high on cocaine and constantly quick cutting itself out of problems.

When I was first taking film studies courses in college, the teacher told me about how he felt like there was nothing like Goodfellas before it came out. At the time, I couldn’t really disagree with him. I had seen, what, a handful of Adam Sandler comedies and your run of the mill mainstream dramas. A little over a decade later and billions of film analysis resources and I still think he’s onto something. We have seen these tropes elsewhere, but Scorsese used them all to inform the narrative of this man flying by the seat of his pants. You love him because of his confidence that he’ll get out of everything okay.

This is why I have trouble admitting this: I don’t love Goodfellas. It probably wouldn’t even be in my Top 5 for Scorsese. As much as I can appreciate its craft and ability to tell a compelling story, its Italian machismo feels like it’s a borderline parody at times. Consider me weak if you must, but this feels goofy and leads me down a certain path. I wonder if gangster movies have unfairly created the image that Italians can only be gangsters. I know that isn’t true, but considering that we have a trilogy of masterpieces in The Godfather, Goodfellas, and the HBO series The Sopranos, there’s already so much affirmation for this trope that it bugs me specifically in Scorsese’s case for reasons that I can’t figure out – which is especially weird because I don’t feel that with The Irishman (2019) at all.

Henry Hill

I can’t say the same for the novel that Goodfellas is based on. Nothing against Ray Liotta, but his portrayal of Henry Hill does NOT compare to the grace of the man himself.

A few years back, I was trying to figure out a way to expand my reading habit and I decided to begin working through books that had been adapted into Scorsese movies. After finding a copy of Nicholas Pileggi’s “Wiseguys” at a used bookstore, I began my journey with one of the most unexpected thrill rides I’ve ever had in the realm of nonfiction. I don’t have a lot of experience reading this more sensationalized form of a biography, but it’s both hard to believe that any of this happened and easy once you begin to understand Hill on a personal level.

Hill was a man who was practically born into a life of crime. If you open up any page, you’ll read about the way that he weaseled in and out of danger at every turn. The people in his life are as colorful as you’d expect, presented eccentric personalities that won’t take no for an answer. 

But what makes him a more interesting antihero to base a novel around is how it feels like he’s giving you all of the dirty secrets. By entering this book, you’re entering the inner realm of his gang, having to watch over your shoulder to make sure that the police won’t barge in and arrest you. You didn’t even do anything, but the way that Hill makes you feel about his criminal activities makes you feel engaged.

This is the feeling that all great criminals have over their audience. Most of us follow certain social norms, never thinking to rob or kill in some form of brotherhood pact. Hill is in a family that feels loving enough, loyal to protect him against other forces. It’s a warped presentation and we’re taken in by the role that everyone plays in keeping this community as stable as it is. This world exists outside of normal reason, and yet it’s often more civil when not faced with violent rivals. What is this world?

Of course, things eventually get out of hand for Hill and he’s drawn into a life of anonymity. Everything begins to spiral out of control. The only thing keeping this from being a just desserts narrative is that Pileggi has humanized him to such an extent that we feel like he’s our best friend on this journey. He doesn’t seem like some indomitable force, but a man who is trying to evade the law. Even as everything begins to spiral into madness, he has this calm about him, again acting like everything is this secret. We lean in, wanting to learn more and Hill plays into our human nature. 

Goodfellas

The thing that is exceptional is that a book can feel so dangerous without ever harming us. It’s a bit hyperbolic, but Hill is a character who is stranger than fiction. Even if it’s doubtful that we’ll ever meet a man like him, we come away immediately like we know him, like we’re meeting up for our weekly chat. It’s so casual, presented in the first person and lacking the legal mumbo jumbo that usually makes these novels dry and boring. No, the crime in this is cinematic, like he’s larger than life. It’s a perfect juxtaposition for his current position where he’s stuck in hiding, having to sacrifice so much just to stay out of jail.

Many despise him by the end, and it’s easy to see why. We question what his loyalty is to. He exists in a grey area that is impressively charming. There’s no point where he was actually morally sound, but we’re still tricked into loving him, as he has practiced for his entire career with the mafia. Even the fact that he’s doing this memoir feels like moral deceit of sorts to somebody, but we’re glad that it exists anyways.

The thing that gets overshadowed is that this is Pileggi managing to make Hill’s story into a compelling piece of nonfiction. In recent decades, there has been more of a push for history to be presented with more of a style. This isn’t just hard facts presented in clear-cut terms. No, Hill is full of moral ambiguity and sometimes it’s hard to trust him and his flippant attitude. While there’s room to argue that he’s improvising moments or aggrandizing others, we’re left with someone who could easily qualify as a Holden Caulfield type. He’s an unreliable narrator, but we want to believe that he’s telling us the truth the entire time.

Seems friendly

By making the audience feel more central with Hill’s story, it engages the reader on such a level that it makes sense why Scorsese wanted to adapt it. The easy answer is that Scorsese’s love of atoning for our sins informs how he treats Hill’s narrative. He makes it more of a Catholic tale of a sinner giving up his evil life in favor of something more boring and righteous. Even then, there’s this blasé approach to the narration that none of it feels like a great burden. He’s just telling us about his day, like if he went to the grocery store and picked up milk. He is like us, only he isn’t.

But I admire Pileggi’s approach to writing Hill’s story because it fully understands not only how to make nonfiction feel more exciting, but how to make Hill’s life more fascinating. What details does he latch onto, and where does he personally add flourishes to make it pop with more life? It’s probably true that Hill writing this would’ve been less coherent and sympathetic, but in the hands of a professional writer, we’re getting a personal look at criminal life. Make it too big and it all seems farcical. Make it too small and the project loses any purpose. 

What I think makes “Wiseguys” so fascinating is how it’s just a good book. There’s no reason that we should care about Hill’s actions. It’s more of a chance for him to boast and come to terms with his past. The author’s job is to make us care, and that is by turning the various interviews into something richer, of a linear narrative. As a story, it’s something as great as any fiction that I’ve read because of how dynamic every detail is, where every word is placed to make you feel its deeper punch. 

I am by no means an expert on the world of nonfiction, but I think of “Wiseguy” as an example of great writing because it first and foremost understands character. Why do we care so much about Henry Hill? This is one of many collaborations that Pileggi did with Scorsese, but I worry that none of them will compare to reading about a man leading us into the seedy underbelly of society, making us see a dangerous world that most of us will never be privy to. Most of all, I doubt it will be presented in a way that warps the reader’s mind and makes us question our own morality when we root on Hill during his downward spiral. He was never a good guy, but we are lulled into believing it by Pileggi’s subtle writing, and I love how it makes you understand Hill’s charisma on a subliminal level.

While I don’t love Goodfellas, I understand what the big appeal is. A lot of what works on screen works even better for me in the book. There’s very little filter on the page, where everything just falls out, forcing you to look in awe at the contents. You can stay on a sentence and reread it, wondering if you read that right (you did). More than anything, it’s a good resource for a variety of reasons, managing to be both a great example of how to make nonfiction engaging and popcorn material but also just how to write a great character. Henry Hill is a real person, but because of “Wiseguy,” I think of him as a character, created in such a way that couldn’t have possibly existed. But he did, and I’m thankful that he had Pileggi to turn to for clarity. 

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