Essay: The Masculinity Of ‘Glengarry Glen Ross’

All the sad dudes

Apr 06, 2025

It is my limited experience that the words one writes and releases into the wild immediately take on their own lives, and if that is true for hacks, then it must be true for novelists, poets, and playwrights.

David Mamet’s Pulitzer-winning 1983 drama Glengarry Glen Ross — a play about cannibalistic Willy Lomans — is enjoying its third Broadway revival this century. Over the decades, it has grown from a long, uncomfortable peek at bottom-feeding real estate salesmen wrestling in the muck to an in-your-face portrait of mainstream American masculinity.

Glengarry Glen Ross is short but brutal, mordantly funny, and depressing. The play is not a full meal, more like a turkey leg—meat and bone.

I’m curious if Mamet knew he was writing something prophetic at the time. That in the 2020s, the President of the United States himself would be a bullshit artist in an ill-fitting suit insulting anyone who dares pipe up. Was he telling us something? Did we listen or chuckle?

As I rewatched the star-studded revival of Glengarry Glen Ross the other night, I wondered if Mamet ever truly understood his play or if he wrote it in an inspired fugue. He knows his characters are vile cowards on some level, but he’s also smitten by these sons of bitches. Or he was. The thirtysomething Mamet who wrote Glengarry Glen Ross was probably the kind of guy easily impressed by cheap displays of machismo, and his creations reflect his infatuation with limp-dicked power plays between soft-boiled alphas.

Mamet had to have been aware of the hoary Latin proverb: Homo homini lupus — man is wolf to man. At the same time, you can tell he finds wolves cool.

This tension between criticism and fascination saves Glengarry Glen Ross from becoming moralizing or treacly. These scumbags deserve what they get, even schlubby, desperate, middle-aged Shelley ‘The Machine’ Levene. He’s two-faced: one begs, whines, cries, the other smiles, teeth shining, while you sign on the dotted line. But the play is at its most exciting when Roma, Moss, and Williamson gnaw on each other’s faces because violence, even emotional violence, gets the heart pumping.

Mamet knew an essential truth about men — we’re miserable. He warned us back in the 80s about what was happening, intentionally or not. Meanwhile, he slyly celebrates his hustlers. They’re modern-day warriors to a nerdy playwright like him. The grind is man’s work, soul-crushing toil. He’s drawn to that right-wing ethos like a toddler compelled to stick a fork in a wall socket.

Like many Boomers, maybe Mamet got punch-drunk on Reagan’s bubbly brand of ruthless, top-down, rich-guy economics one night at the typewriter? Who knows. It’s depressing how little American life has changed: third prize is you’re fired. The only perk? Cruelty. Man is asshole to man.

And now, every minute of every day, across multiple cursed social media platforms, friendless men snipe and cuss at each other because that’s their only coping mechanism and also because it feels good to lash out.

***

The America of Glengarry Glen Ross is devoid of women. And children. They exist offstage, in another dimension. There’s no art, no joy. It’s a dim basement populated by gloomy, sexless men who comment on their various fortunes, complaining and/or crowing. This vision of masculinity, as a rigged game that never ends, is so hopeless one has to imagine Sisyphus happy he’s not selling real estate.

What exactly are Mamet’s salesmen selling? Swampland, with fancy pastoral names like Glengarry Highlands and Glen Ross Farms. They’re selling cut-rate hope marked up steeply to wannabes and strivers. It’s a numbers game for these mooks; they need as many leads as possible. That’s the hustle. It’s like the old Arnold Palmer saying: “The more I practice, the luckier I get.” These guys need “leads” — all-new suckers — a steady stream because the game is luck. Chance. Every lead is either a yes to exploit or a no to dispose of.

After a long losing streak, Levene barges into the office in Act Two, shouting about a big score. He sold eight units of Mountain View—eighty-two thousand dollars. The man is alive, and he wants to brag. How did he do it? He tells the story — blah blah blah and ultimately, it doesn’t matter because his job doesn’t require any skill. It’s slots. He just talks as the reels spin.

To truly get Glengarry Glen Ross, you must spend time with the third scene in the first act, the last of three two-handers that set up the explosive second act. Each is a seduction, where men try to get something out of other men and move them to do things against their will. Sell. Persuade. Bully. They all happen in the same location: a rundown Chinese restaurant across the street from their messy desks where they drink, eat, and talk shop. Bitch and moan. It’s the closest thing to a safe space they have.

We first learn that Levene is in the dumps there—scene one. There’s a contest for top salesman — first prize is a car! — and his name isn’t even on the leaderboard. He begs office manager Williamson for the good leads, which are dangled but denied. In the second scene, two salesmen, Moss and Aaronow, plot an office break-in to steal the good leads. Well, one plots, the other listens and is looped in whether he wants to be or not.

Then, we meet Ricky Roma, who is a closer. At that moment in time. He’s hot. Roma is always played a macho leading man type, someone with rizz. This current production? Not so much. As he’s written, though, Roma is a winner. The contest is his. He will drive around Chicago behind the wheel of his new Cadillac, looking for chumps.

Roma will have you believe that he earns his commissions when the trick of his trade is figuring out how to be at the right place at the right time. Simple. Capitalism is a casino. It is a binary. You are up or down, broke or flush. You are young, like Roma, or you are old, like Levene. When you’re on a roll, you think you’re on a roll forever, and if you’re Levene, your failure is an inescapable force of nature like gravity. Roma is making money. He’s on top… for now. The odds smile upon him, but his day will come. You can’t beat the house.

But Roma will worry about that another day, or maybe his fall will be a terrible surprise. He thinks he’s better than his coworkers, but he’s just another testosterone-drunk weasel, a backstabber/frontstabber/sidestabber. None of these guys know where the truth begins and the lies end. Even Roma’s affection for Shelley is a schtick.

When Roma is introduced, he can’t believe his good fortune: a mark, James Lingk, has just magically appeared right in his backyard. Roma didn’t have to cold-call this one or knock on their door. He was having a drink on the clock, and abracadabra a fragile cuck.

Lingk is insecure and lonely. He’s a heap of smoldering resentments who is instantly hypnotized by Roma’s rehearsed sales pitch, a freewheeling prayer about sex, gut feelings, and bold risks. His speech sounds spontaneous and confident, but Roma is just scratching another lottery ticket here. Maybe he’ll hit the jackpot, or maybe he won’t.

Mamet’s men are racists, and why wouldn’t they be? There were racists then, and there are racists now. The least surprising thing about America is its overabundance of people terrified of other people. Mamet peppers his dialogue with homophobic slurs, too. Everyone and anyone can easily threaten these guys. When the play opened 40 years ago, white men were firmly in charge of American society, and that’s just an easily provable fact. Fast-forward to now: white men are still doing pretty well. We’re solidly in control of all the money, power, guns, commerce, and law. We have all the judges, cops, and politicians, but there’s slowly growing competition from others, women, and people of color, and that’s scary—real hair-raising shit for some.

The salesmen in Glengarry Glen Ross do not want to compete with Indians or gay men or other white men, so they’re mean. Some men confuse being mean with being strong. Scroll through any social platform; those kinds of dudes are easy to find. They’re your family, your neighbors. You don’t even have to go to the Chinese restaurant across the street.

This was originally published on Medium.