Prologue (A Kid from Boston)

“I can’t learn anything from you I can’t read in some fuckin’ book. Unless you want to talk about you. Who you are. Then I’m fascinated, I’m in. But you don’t want to do that, do you sport? You’re terrified of what you might say.”

– Sean Maguire

When I was a kid, I used to run straight upstairs when I got home.

“Oh, straight up to your bedroom to watch TV,” my friends in law school would nod knowingly when I dove into this story, unaware that our home didn’t have an upstairs, and I certainly didn’t have a television in my room. But I’d abandon the tale. It wouldn’t be very interesting to these people, anyway, I’d tell myself. And it might embarrass me.

It doesn’t anymore.

When I was a kid, I used to run straight upstairs when I got home because my grandparents lived upstairs. My Dad was probably still at his manufacturing job, an hour’s drive away. My mom was likely finishing up her day as a nanny, before heading downtown to her night job in retail—I think she sold sunglasses and clothes, but I’m not sure. My parents didn’t talk about that stuff.

I’d scramble up the rickety wooden steps, busting through the door without knocking. There was usually a plate of brownies or pizzelles (my grandmother was full-blooded Irish-Catholic, but she married a full-blooded Italian-Catholic, and so did her cooking and baking) waiting for me, because however sly I thought I was being, my intentions were quite transparent. I’d ask my gram if we could play a game, and sometimes I’d ask if she’d take me to the movies, or if we could go into the city.

“Into the city” meant downtown, as in downtown Boston. To get there we took the 73 bus, which dumped us out in Harvard Square, where we’d take the red line to the Park Street station. But before we made the transition from wheels to rail, I’d stare up at that hallowed red brick of the most famous university in the world, just a short, bumpy ride from my home.

My parents didn’t go to college. My dad enlisted in the army after high school, joining the manufacturing company back home when he got out. It’s changed names—corporations, unable to feel shame, shed their skin and reinvent themselves more freely than people—but he still works for the same company, more or less, almost 35 years later. He’s worked his way off the factory floor and into an office. My mom graduated high school fourth in her class, but her family couldn’t afford college. She got married a week after she walked across the stage in rural Michigan. She had my sister a year later, and a year after that moved to the same five-block radius in which every D’Amico had lived since Francesco stepped off the boat just before the Great Depression hit.

And so I’d gaze up at those hallowed halls of higher learning, blinking the sun out of my eyes as it rose over the Yard. I’d shake the cobwebs of yearning and admiration out of my head. And I’d mutter to myself, usually something along the lines of: “pricks.”

What can I say? I learned from the Matt Damon characters I knew growing up: Will Hunting, Tom Ripley, and Mike McDermott. I don’t know if, as a young actor from Boston, Damon struggled with his identity. But I know the roles he took helped me find mine.

Act 1 (The Bright Future)

“How do you like them apples?”

– Will Hunting

Welcome to the rest of your life.

There’s a jarring cut early in Good Will Hunting that shows the power of montage in cinema, and that forecasts the central tension facing Will (Matt Damon). He’s messing around in the batting cages with his buddy, Chuckie (Ben Affleck). Replacing the lifeless pitching machine, Will throws pitches to his childhood best friend, playing the chin music, tossing the ball closer and closer to his head. Chuckie eventually charges, and the two start a mostly loving brawl, and then—

CUT TO: four cardinal red jackets, not a single thread out of place. Silky voices, a capella, crooning to the crowd. It’s the MIT class reunion. Their fun is not rough around the edges; it is mannered, planned, precise. This is what success looks like.


This visual juxtaposition highlights the existential impasse facing a trio of early-career Matt Damon characters: the battle between the person he is and the person he thinks the world wants him to become.

Will is, as his eventual therapist says with a mixture of disbelief and admiration, “a boy genius from Southie.” He’s also a janitor at MIT, a short drive from Newton North High School, where my grandfather was a janitor for 27 years. When Will goes from L St. Tavern in South Boston to a bar at Harvard, schooling the blonde-ponytailed, entitled Clark on early American economic evolution, he lives the intellectual schadenfreude dream of so many kids who grow up without. Our fantasy is not to get the things that others had—it’s to show those others that they aren’t better than us, and to show them in our own smackdown sort of way.

But the 15-minute red line trip from Broadway to Harvard Square is a deceivingly short, deceptively straight line.


When I was 14, I floated slightly above my body, in the trees a few blocks from school, watching myself watch a classmate get curb-stomped. The perpetrator was a mercifully inexperienced teenager; the lack of a nearby curb replaced with a tree root—the boy was okay after some minor dental work, a comparatively fortunate result if you know anything about curb stomping.

What the fuck was I doing?

Running from the future. The closer I inched toward that looming leviathan of higher education, the further I regressed into whatever made-up image of my past I had constructed for myself. My parents hadn’t needed college. The white-bread parents I knew who had gone? Conceited barneys, one and all. So I sprinted backwards. I did everything I could to prove that I was the idiot brawling with his pal in the middle of the batting cage, not the well-mannered “university man” singing a capella for the occasional vicarious thrill. I’d rather be boarish than a bore.

I watched Good Will Hunting a lot as a kid. I mean, a lot. I’m not one-one hundredth as intelligent as Will, but you’re damn right I wanted to be him. I wasn’t hallucinating the antiseptic halls of an Ivy League school, though, and I definitely didn’t daydream of blackboards crowded with crawling equations. That’s not what makes Will Hunting a cult hero in Boston to this day, and it’s not what led me to my mirror every morning to try and perfect Matt Damon’s aw-shucks half-smile.

No, I wanted to send my own Chuckie to a job interview to ask for a “re-taiiiiiin-errr.” I fell asleep at night thinking of telling some Harvard-educated lawyer that he was, in a word, “suspect.” My highest aspirations were to get invited into the smoke-filled halls of higher learning and to tell those boat-shoes-wearing, scotch-drinking, faux-polite pricks to go fuck themselves. I wanted to take their jobs and ask them how they liked them apples.

Until one cold December day seven years later when my consciousness lifted itself out of my physical body once more. This time, I had been accepted to Harvard Law School.

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“Fuck you, you don’t owe it to yourself, you owe it to me.” – Chuckie Sullivan

Raised by his mom in a communal Cambridge home—the same mom he brought with him and hugged tightly when he won the Best Screenplay Oscar for Good Will Hunting—Damon wore his Boston-area identity like a badge of honor as his career blossomed. He donned a worn out Red Sox cap wherever he went. Upon winning that Oscar, the first words spoken by the telecast announcer were “Matt Damon and Ben Affleck are childhood friends.” And in his speech with Affleck, Damon’s Boston spirit outweighed his Movie Star Cool, as he just started screaming the names of people in his life: his mom, his dad, and “everybody back in Boston.” Damon was, and always will be, the kid from the neighborhood who made it big.

Good Will Hunting launched Damon from the shadows of Harvard into Hollywood’s stratosphere, but for all the time it spends with him, the film often treats Will like a black hole of potential. The expectations of others swirl around him, pulling here, pushing there, all slowly coalescing into a soup of toxic hopes and dreams superimposed onto Will’s psyche.

For men of means, men of things, success is about presence. Presence of something others can see. Something others can respect. Professor Lambeau (Stellan Skarsgård) cloaks himself in the sheen of his Fields Medal, and he wants the same for Will, nudging him without subtlety towards “importance”—in his career, his associations, his life.

For those who grew up with Will, without things, success is about absence. Chuckie couldn’t tell you the difference between one of Will’s dozen job opportunities, but they each offer something “better than this shit.” They each give Will a “way outta here.” Get out of South Boston, get out of a lower-than-middle-class, blue-collar life, and who cares what you do?

Yet for all their differences, the esteemed MIT professor and the guy who spends his Saturdays picking fist-fights to avenge boyhood slights are effectively on the same page: Will should move on to something better. He owes it to the guys who will never leave. He owes it to the mathematicians who’ve struggled for decades with problems he can solve in his sleep. He owes it to himself.

Like any good Irish-Catholic from Boston, with looming expectations and an uncertain future, Will regresses. When his therapist, Sean (Robin Williams), talks about how his own father laid brick so he could have an education, Will hides behind the safety of so-called honor:

Exactly. That’s an honorable profession. What’s wrong with—with fixing somebody’s car. Someone can get to work the next day because of me. There’s honor in that.

But Sean calls him on his bullshit. He identifies his regression as a byproduct of fear. “You could be a janitor anywhere. Why did you work at the most prestigious technical college in the whole fucking world?”


When each summer rolled around, my peers in college would travel to Washington, D.C. for unpaid internships in their senator’s office, or trade a dorm room for a Manhattan studio to taste the highs of high finance. Me? I was back home, working in the machine shop at the same manufacturing company my dad had been with for a quarter century. And if I’m being honest? I had more to talk about with the career assembly-line guys than I did with most of my classmates.

And as my senior year of college came to an end with a decision looming before me, I was nothing more than a “cocky, scared-shitless kid,” as Sean calls Will. I contemplated going home, working another summer on the factory floor, maybe even picking up that job full-time. I didn’t understand it at the time, but I was afraid of the unknown. Terrified of the expectations I believed my parents had for me. For all the jitters I felt when I thought of failing, I was completely paralyzed by the thought of selling out, of facing the kids I grew up with after I became one of those pricks I grew up hating. What would Will or Chuckie say if I came home wearing boat shoes and a smoking jacket (whatever that is)?

Working with my dad was comfortable, honorable. But he sacrificed everything to give me an education. And Sean’s words, the ones I’d heard so many times, kept ringing in my head: “Right, and that’s honorable. Sure, that’s why you took that job. I mean, for the ‘honor’ of it.”

 Like Will, I’d spent my whole life trying to chase after an image of myself that my guidance counselors seemed to project five feet in front of me at all times. In all that time, I never stopped moving long enough to ask myself what I wanted. As Sean asks Will:

What are you passionate about? What do you want? I mean there are guys who work their entire life laying brick so their kids have a chance at the opportunities you have here.

Those “guys” were my parents, who had sacrificed so much. And that opportunity was Harvard Law School, a place I’d applied to for no other reason than it was how I’d learned to define success. It had presence, a presence that Professor Lambeau would respect. And it gave me a “way outta here”—it sure as hell would’ve made Chuckie proud, and I imagined my dad knocking on my bedroom door, ready to take me to work, hoping like Chuckie did that he’d show up one day and I wouldn’t be there.

And that’s how, 15 years after I looked up at the crimson brick and earned a grandmother-powered whack on the back of my head for muttering “pricks,” under the tutelage of Matt Damon, I ended up walking into Harvard Law School.

It was an opportunity my parents had “[worked] their life” for, as Sean said. It was a chance that countless people would “do anything” for, like Chuckie said. It was my first step into a new world full of unknown possibilities.

It was the biggest mistake of my life.

Act 2 (The Past Is Never The Past)

“You’ve gotta get a new jacket. Really. You must be sick of wearing the same clothes.”

– Dickie Greenleaf

There’s a small moment that may have slipped past you in the opening sequence of The Talented Mr. Ripley. It’s a drop in the bucket compared to what’s to come, really, but it slams home like a sudden left hook for anyone who has carried out an existential charade to stave off feelings of insecurity and inferiority.

Tom Ripley (Matt Damon) has just helped out a friend by playing piano at an upscale cocktail party. With his friend’s Princeton jacket draped over his gangly shoulders, Tom has been mistaken for an alumnus by the Greenleafs, whose son graduated a few years prior. A few well-placed white lies later, Tom is bustling out of the party to his job as a men’s room attendant at a theater, a proverbial invitation in hand to visit the wealthy couple. As he skids across the street, Herbert Greenleaf (James Rebhorn) looks after him, and mutters softly but admiringly to his wife: “An exceptional young man.”

Herbert Greenleaf met Tom Ripley. The limber fingers on the piano? Tom. The boundless conversationalist who can keep up with an erudite shipping magnate? That’s all Tom. But that’s not why a man like Herbert Greenleaf called him exceptional. Without his friend’s jacket and the fake Princeton degree, Tom Ripley is nothing. At least, that’s what Herbert believes.

And when Tom accepts Herbert’s offer to go to Italy and bring Herbert’s son, Dickie (Jude Law), home, he takes the same approach with the junior Greenleaf. Tom is painfully straightforward with Dickie about who he really is, describing his talents as “forging signatures, telling lies, impersonating practically anybody,” before gleefully revealing the assignment from Dickie’s father. But when it comes to high society, it’s not what’s on the inside that makes a man—it’s what other people can see. It’s the way you talk; the clothes you wear; the things you like. And so even as he grows close with Dickie, Tom remains an imposter: a Princeton grad, a jazz-lover, a well-dressed mannequin of a man.


In screenwriting books, get-famous-quick gurus explain how to build trust step-by-step, as if you’re building a dog house. First, put your protagonist in a position of vulnerability with someone. Second, give the other character the opportunity to expose that vulnerability for their own personal gain. Third, the other character chooses to respect the protagonist rather than act selfishly. Boom. Get trust quick.

What a load of nonsense.

One month into my ill-advised foray into becoming a “Cambridge man,” I had my first experience at a very specific type of event: the function whose purpose was to give us a chance to show not who we were, but who we appeared to be. Opportunities to drink copiously, dress gloriously, and network shamelessly, these occasions require nothing less than formal attire.

The problem? I didn’t own a suit.

I approached someone I’d met in my first few weeks—he’d gone to a private high school, an Ivy League college—and head-down, hands stuffed into my pockets, asked if I could borrow one. “Of course,” he exclaimed; kindness comes easy when you have everything. And the opportunity to dress up the blue-collar kid of the class, She’s All That-style, was unfortunately not one that this Dickie Greenleaf could keep to himself. He told everyone.

Shame is a powerful thing, and it almost always lodges deeper in the psyche of the person being shamed than the ones doing the shaming. The insecurities that Tom feels when Dickie guffaws to Tom and Marge, “you’re so white, you ever seen a guy so white?” far outlast any ridicule Dickie hopes to convey with his offhand remark. And the laughter of “friends” at my sartorial expense stuck with me for years.

Luckily, I had a model. I’d seen The Talented Mr. Ripley enough times, and I had plenty of experience as a social chameleon. I learned how to speak properly—jokes at others’ expense and references to obscure, high society cultural touchstones. I spent hundreds of dollars of my loan money at J. Crew, falling further into debt in order to dress the part of a Greenleaf. Like Will Hunting, I hid my past from my new Harvard friends.

As a child, I hid my envy for Ivy Leaguers with disdain; as an adult, I did everything I could to become one. I justified my behavior, telling myself I didn’t want to become one of them, I just needed to look like one—I could impersonate my way to success. But when does pretending become being? If you work so hard to convince someone else of your identity, at one point do you start to convince yourself?

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“Don’t you just take the past and put it in a room, in the basement, and lock the door and never go in there? That’s what I do.” – Tom Ripley

There’s always a Freddie Miles.

Not enough can be said about Philip Seymour Hoffman’s menacing performance as an entitled, skeptical, gallivanting acquaintance of the real Dickie Greenleaf. In his first scene in The Talented Mr. Ripley, Freddie speaks briefly to Dickie, as Tom looks on, quiet, uncertain of his place in this new dynamic. “Tommy, come on,” he beckons Ripley to follow him and Dickie to a new restaurant. With a few glances, Freddie plants a seed of insecurity in Tom that will blossom over the next hour into full-grown self-doubt. And by refusing to pay him any more attention than he needs to, Freddie sends a clear message to Tom: you are not one of us, and you never will be.

No matter how long he wears his new skin, Tom cannot escape this fear. It’s present when Dickie catches him masquerading in his wealthy patron’s clothes, as he begs, “I was just fooling around, don’t say anything.” It seeps out when Freddie catches him peeping on Dickie and his fianceé, Marge (Gwyneth Paltrow). And ultimately, it’s this fear that drives him to kill the real Dickie Greenleaf and assume his identity—when Dickie mocks him moments before death, telling him “you can be a leech…you can be quite boring,” he triggers it.

But understand: this is not just anxiety that he will be found out, revealed as a fraud. It’s an all consuming terror that Tom Ripley is not somebody. Tom has blurred the lines of his identity to the point of convincing himself, and as the walls come falling down around his ruse, he digs himself deeper. Tom Ripley becomes Dickie Greenleaf.

In a final, haunting moment, Tom has escaped the rapidly deteriorating charade unscathed—he sails to a new life with a new lover, Peter Smith-Kingsley (Jack Davenport), and a promised inheritance from Herbert Greenleaf for being such “a great friend” to Dickie. The ultimate con has gone off without a hitch. But in his heaving rush to avoid crossing paths with another of his many winding identities, he refers to himself as Dickie in front of Peter. Resignation overwhelms him. He must kill Peter. As he wrote earlier in Dickie’s forged suicide:

I realize you can change the people, change the scenery, but you can’t change your own rotten self. Now I can’t think of what to do or where to go. I’m haunted by everything I’ve done and can’t undo. I’m sorry. I’ve made a mess of being Dickie Greenleaf, haven’t I?


I did not murder the Dickie Greenleaf of Harvard Law School. I killed the Zach D’Amico of the prior 22 years.

It happened slowly and it happened all at once. Suddenly I hadn’t spoken to friends who knew me, who really knew me, for months at a time. I walked into the annual D’Amico family Christmas, proudly clad in chinos and Clarks and a button down, to a step-back, double-take, who’s this guy? look from my Uncle. I wasn’t just wearing Clarks, I was Clark, the pony-tailed douchebag from Good Will Hunting. I was no longer one of the brawling buddies; I was one of the blazer-clad a capella singers. I was the guy Will’s Harvard girlfriend Skylar (Minnie Driver) was talking about, when after Chuckie tells her she changed his opinion of Harvard people, she responds, “Well you don’t want to rush to judgment on that one, because they’re not all like me.”

I’d shoved my past so far down into that basement, buried under boxes of new clothes and new friends and new phrases and new everything, I couldn’t find it anymore. Yet at the same time, despite my seemingly successful integration with the Harvard crew, I felt as insecure as Tom did. Freddie Miles lurked around every corner, waiting to expose me for the fraud I was.

And so when I met Sara Murphy, a woman with the compassion of Sean Maguire who had no interest in a prestigious “Ivy League” man, I didn’t “toss her the key” to that basement. I didn’t say “open up, step inside.” As Tom Ripley says, “you can’t, because it’s dark, and there are demons, and if anybody saw how ugly it is…” I kept her at a distance. I idiotically assumed that if I let her in, Sara would drop me so she could brag that “she went slumming too once.”

2014 was one of the worst years of my life. From the second-half of my first year in law school through the first half of my second year, I was nobody. And not a nobody like Chuckie Sullivan or Tom Ripley felt like a nobody. I was nobody because I had no identity. I’d fitted a new identity over my self; when that self withered and died, I was left with an empty shell.

And that’s when Matt Damon saved me. Well, okay, that might be hyperbole. I wasn’t aware of the impact of his movies on me while I was growing up, but as I neared rock-bottom in early 2015, he came roaring back. I sat with a small group, drunk, at 1:30 a.m. Sara was there. We went around the room listing our top five movies. She named Good Will Hunting. And everything I’d buried—my anxieties and insecurities, but also my convictions and values and idiosyncrasies—broke their way out of that basement.

Forget about being Dickie Greenleaf. Forget about getting the respect of Professor Lambeau.

I had to go see about a girl.

Act 3 (The Present Is A Present)

“You know what cheers me up when I’m feeling like shit? Rolled up aces over kings.”

– Lester “Worm” Murphy

Massachusetts Senator Elizabeth Warren has a saying when she feels passionate about a particular policy. “You can tell a lot about a country by how it treats people when they’re at their lowest.” It’s a macro-level statement; a way of merging a value system with a governing philosophy.

But as Rounders taught me, it’s a maxim that works just as well on a personal level—you can tell a lot about a person by what they turn to when they’re at their lowest. When law student Mike McDermott (Matt Damon) becomes a moot court jester instead of the next John Grisham novel hero, he turns to the felt to ease his pain. When his girlfriend, Jo (Gretchen Mol), drops him, he runs straight to his poker buddies in Atlantic City.

And most telling, when the poker savant gets beaten to a pulp at the table—literally and figuratively—where does he go? Right back to it.


More of our lives are impacted by movies than we might think.

Take the climactic moment of realization, for example. It was a rainy December day in 2017 when I slouched into the apartment I shared with my then-fianceé Sara Murphy, sopping wet, indecipherable politico-babble spewing from my mouth. Working in progressive politics had been emotional torture since November 8, 2016, but that day had been particularly cruel. After weeks spent trying to stop a trillion-and-a-half dollar giveaway to the wealthiest Americans, we had failed.

I was, in a word, inconsolable. But Sara knew me better than I knew myself. Rather than repeated futile efforts to cheer me up, only to be rebuffed by my intransigent misery, she grabbed my MoviePass (RIP), turned me around, handed me an umbrella, and marched me right back out the front door. “Go see Lady Bird again.”

And I did. And it helped. Without cinematic tropes, I would have let that moment fade into history (along, hopefully, with Mitch McConnell). Instead it’s imprinted on my movie-fed brain as a climactic turning point in my journey, the essential protagonist revelation that kicks the rest of the film into gear.

And for the next few years, the sequels have come hot and heavy. Professional problem? Go and see Dog Day Afternoon at the AFI Silver theater. Relationship troubles? Invest that into my screenwriting. Frustrated? Alone? Depressed? Read, write, watch. Movies, movies, movies.

There was just one problem—I was still a cocky, scared shitless kid. This time, I was terrified of what people would think. I had stopped trying to be someone else in law school, but I had started trying to be a version of myself that I thought the world wanted. I’d made it—gone to college, law school, left home. I owed it to my parents to use the degree they never had the opportunity to earn. I owed it to my Chuckie Sullivan, to my Gerald Lambeau. And what would those Harvard kids think? The ones I’d worked so hard to convince I was one of them? I couldn’t do anything else. It was too late.

But as Mike McDermott said, “If you’re too careful, your whole life can become a fucking grind.”


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“What choice?”

– Abe Petrovsky

Rounders follows in the footsteps of Good Will Hunting’s Eisensteinian use of montage: as a dialectic for exploring the perpetual conflict between thesis and anti-thesis. In the case of early career Matt Damon, juxtaposition exposes and aggravates the tension between who he’s trying to be and who he really is. “We can’t run from who we are,” Petrovsky tells Mike. “Our destiny chooses us.” After losing his girlfriend and fleeing to the Taj poker room, Mike sits at the bar with his degenerate buddy Worm (Edward Norton), making the only choice he can: to go on a 72-hour run with Worm to scratch out the money Worm owes.

CUT TO: Mike running down a garishly formal hallway, legal papers stuffed under his arm, stumbling late into his moot court. His body goes through the motions of complying with the obligations of Law School Mike, but his brain has already made the choice. As he tells Petrovsky later, “I was on my way out anyway.”

But we cannot live successfully in two worlds. If our destiny chooses us, we must then choose to give up the rest. Mike tries to succeed at both, but ultimately he’s forced to kill the respectable life he’s created for himself—he abandons law school and jumps head-first into the great beyond of his own destiny. And that’s a process that defined the early part of Damon’s career: To fully inhabit Dickie Greenleaf, he must kill Tom Ripley (among other people); to have any chance of finding his own Eudaimonia in Good Will Hunting, he must physically leave behind everything he’s ever known.

“I told Worm you can’t lose what you don’t put in the middle,” Mike narrates after his penultimate match against Teddy KGB (John Malkovich), halfway out the door with enough winnings to pay back what he owes. Then he turns back around, making that climactic decision, the essential protagonist choice that kicks the rest of his life into gear, and returns to the table.

“But you can’t win much either.”


I’ve spent the last 10 years following the paths that my parents, my friends, my classmates, and my colleagues expected me to follow.

Nope. That’s not true. There I go again.

Take two: I’ve spent the last 10 years following the paths that I thought my parents, my friends, my classmates, and my colleagues expected me to follow. The imaginary expectations I saddled myself with to avoid making a single decision about what I wanted, because if I didn’t decide what I wanted, I couldn’t try to get it; if I couldn’t try to get it, I couldn’t fail.

“Look at me. What do you want to do?” Sean almost spits this at Will in a therapy session late in Good Will Hunting, the words flaming out from his mouth like he teed them up on his tongue before breathing accelerant out from his lungs. “I ask you a very simple question and you can’t give me a straight answer. Because you don’t know.”

I know. I think I’ve known for a while, but I was too busy trying to escape my past or manufacture a future for myself to stop and answer that simple question. I want to write movies and I want to write about movies. I want to help make movies and I want to help people see movies.

I’ve never admitted that before.

Epilogue (The Great Unknown)

“First prize at the World Series of Poker is a million dollars. Does it have my name on it? I don’t know. But I’m going to find out.”

– Mike McDermott

Making it in the film industry? I’ve heard the odds are against me. I’ll probably fail.

But hey, at least I won’t be unoriginal.