On a recent weekday afternoon, a little too early in the day and too few cocktails in to be as drunk as we are, the actor David Costabile is laying out the kind of lesson you learn only from close and sustained contact with the richest people in the universe. “When somebody invites you to the Skybox, your answer is, ‘Yes,’” he says. “It's called the Skybox. I mean, nobody has a Skybox that's in, like, a dungeon. It's a Skybox, for god's sake. So, your answer is just, like, ‘Yeah. I'll go to the Skybox.’”
The Skybox in question is the exclusive space at Daniel, the Manhattan restaurant perennially ranked among the world’s finest. Costabile had been there to shoot an episode of Billions, Showtime’s supercharged financial drama. An invitation to stick around for a drink after a long day of work was proffered. He went to the Skybox. You don’t say no to the Skybox.
This is one of the perks of Costabile’s role as Wags, the hedonistic, mustachioed COO of Axe Capital. The show makes a point of filming in the kind of restaurants, hotels, and homes its high-flung characters—billionaire hedge fund manager Bobby Axelrod (Damian Lewis) and erstwhile US attorney Chuck Rhoades (Paul Giamatti) among them—might frequent. In shooting the show’s four seasons, Costabile has been to dozens of versions of someone’s favorite restaurant. Sammy’s Fish Box on City Island. Wolfgang’s. In one of the show’s more delightful moments, he cussed out an insufficiently respectful finance bro at Sushi Nakazawa. And then, of course, he went to the Skybox.
But spending time there also went against just about everything Costabile has learned in his long, steadily churning career. “All of a sudden you get in the Skybox, and you're like, ‘I can't fucking believe it.’ But the thing to remember is that you're not going to stay in the Skybox. You can go to the Skybox right now. You got invited to the Skybox.” And in his line of work, unless you’re a Brad or a Denzel, that invitation is permanently subject to revocation.
From our vantage point at the bar at the venerable New York chophouse Keens, though, things are looking pretty good. Between sips of his Manhattan, perfect (equal parts sweet and dry vermouth, he explains), rocks, Costabile, 52, elaborates on the strange world he’s come to inhabit. And on the fact that, some 20 years into a career full of That Guy roles on legendary TV shows—quirky chemist Gale on Breaking Bad, icy Baltimore Sun publisher Klebanow on The Wire, characters on Suits and Damages, even a single episode as an anonymous banker on The Office—he’s found a job that is the longest-running of his life, and quite possibly the best time, too.
Billions isn’t particularly generous to the ultra-wealthy, necessarily, though it does abide by their preferred logic: that being super rich can, in fact, be super fun. And no one is having more fun than Wags. As the swashbuckling COO of a Death Star-like hedge fund, the character finds his calling in making his boss’s life easier—whether by securing him a place in a “luxury security bunker” or wining and dining (and dancing and drugging) potential clients.
Initially, the role was written to be the brash Axe’s quiet, stately, WASPy consigliere; Wags barely appeared in the pilot. But by the time the series was picked up, the show’s creators realized who they were dealing with. In conversation, Costabile is genial, hyperverbal, operatic, and alarmingly truthful. If he is an uncle, he is the kind who introduces you to pot. Some actors are said to chew on scenery. At his best, Costabile is a human Vitamix.
So Wags transformed into a different beast entirely. Wags calls out to the office things like, “Body sushi at the strip joint, on me!” Wags wears a little bit too much man jewelry. Wags studies Esperanto. This is all meant to be a bit tongue-in-cheek. No one’s supposed to look at Wags, who wakes from a blackout with a tattoo of Yosemite Sam on his ass, and see someone aspirational.
And yet, and of course, Costabile has become a hero on Wall Street. He’d be ringing the bell to open the New York Stock Exchange the next day. This, he granted, would be worth it. “It is the closest thing I've ever been to being a rockstar. I go on that floor and people go fucking apeshit,” he says. “And it is so fun. And I'm just like, Who knew that pressing a button would be so fucking fun? Something like that, you get entrance to a part of New York City where you're just, like, Nobody gets to do this shit.”
Costabile came to town to attend NYU’s graduate acting program in 1992, and he’s lived in the city ever since, which has taken no small amount of endurance. Becoming a That Guy in this town, it turns out, entails just a spectacular number of terrible auditions, many of them under shitty fluorescent lights in dingy Midtown office buildings.
Costabile’s own acting process relies on easy, replicable access to a sense of joy, which those auditions seemed precisely calibrated to stamp out. So, to recover from the cattle calls, he’d hoof it over to Christie’s auction house. He’d look at the stuff on exhibit—paintings, sculptures, maybe musical instruments. And he’d feel restored.
So that’s where we meet. He explains that, years before he’d have a chance to use it, he learned another funny lesson about monied New York: rich people don’t have to dress well. “Some guy came in in a tracksuit with his wife,” he recalls. “He dropped three-quarters of a million dollars and fucked off. It was so fucking crazy.”
And if the good folks at Christie’s were ready to let that villain stroll around, then why couldn’t a twentysomething David Costabile, in the suit he’d worn to his audition, share the same paint-fumed air? But Christie’s wasn’t just a place to blow off steam: “There's always a bathroom—you can use the bathroom and nobody will say shit to you. All you can do is pretend. And you know, that's my job, so...” He trails off. It’s not all limos and talk show appearances, kids.
That comfort with anonymity would serve Costabile well: over the next decade or so, he’d grind out a career. He appeared on all three branches of Law & Order. He originated a role in a Tony Kushner play. He was dynamite as a bureaucrat. He looked like...a guy.
Something funny happens, though, when you get good enough at looking anonymous to play a hundred anonymous guys: people start recognizing you.
Which is what happened almost immediately after we entered the only active gallery at Christie’s, that day hosting an online auction of decorative Chinese teapots from the 1990s. Costabile was wearing dark jeans, a blazer, and a colorful scarf: the uniform of a Park Slope-dwelling actor dad—but also, conceivably, of a zillionaire with a soft spot for teapots. Today, the disguise doesn’t work. “Aren't you on Billions?” a staffer asks. “Great part, terrific.”
We make a pit stop across the street, at La Maison du Chocolat, so Costabile can pick something up for his wife, and decide to set off downtown for Keens. The recognition bit, he concedes, happens a lot. “Most people,” he says, “look at me like, ‘You're that guy. What's your name?’” He doesn’t mind it: “On some level there is something very nice about being that, because it allows me the freedom inside of my job to do lots of different things. I do comedy and drama. And I play fat guys, and ineffectual losers.” Whatever he’s doing, he’s easily recognized as that.
But being that guy also means that people feel a sort of claim upon your time, even if they haven’t bothered to look up your name, and not ten minutes later a thirtysomething goon in a blazer and sunglasses interrupts Costabile at a Sixth Avenue stoplight: “Hey, you’re the actor! How you doing?”
Costabile exchanges pleasantries, but the guy goes blank, surprised that his round of celebrity bingo isn’t over yet. As we wait for the light to change, he freezes, glitches, reboots. We’re about to cross when he blurts: “Billions!”
“There you go,” Costabile says, patiently. “You got it.” We keep walking.
We’re finishing our round at Keens, where somehow one afternoon cocktail has taken on the weight of three, when I ask a question about ambition. The bourbon is interfering with Costabile’s answer, so he lets me in on a secret—“I usually only reserve this for my students. This is the first time I've ever gotten drunk off one drink, and talked to somebody about it”—in the form of a story about a pilot season, years ago, when all seemed lost.
He was in Los Angeles, he says, “going out for a relentless string of poorly written, not-funny television shows.” He’s got a complicated relationship with the place: in New York, he explains, casting directors are kind enough to make their displeasure with your audition crystal clear, while their West Coast counterparts will write you off while simultaneously complimenting you.
And anyway, he explains, auditioning is its own very special kind of hell, no matter where it happens. Or, rather, not the auditioning so much as the leaving: “There is a moment when you finish the piece that you've been given, and you have to stand, and you have to walk to the door. And it is a horrific desert.”
You are reminded, he says, of the “tiny, tiny time that you have on the planet,” and the fact that “you've chosen to abuse it in this particular horrific way.” All you have to do is stand up and leave the room, and yet that is precisely the most difficult thing you can imagine in that moment. “You would try every world religion, at that point, anything you could grasp at,” he says, to bridge that divide. But that year, the divide just wouldn’t shrink.
So Costabile asked his friend Glenn Kessler for advice—they were serving as each other’s acting coaches at the time. (Glenn Kessler would go on to create Damages, on which Costabile would have a 16-episode run.) Glenn gave him the holy grail, but not before offering a warning: “This is only reserved for people who are experts. You can only do this if you've done your 10,000 hours of auditions,” Costabile paraphrases.
But he was desperate. He was ready. “I had really reached the nadir of my auditioning process,” he says. (“You can also only do it if you understand what the word nadir means,” he jokes.) So Glenn laid it on him: When you have this moment, you stand, and you look at them, and you say the word “delicious.” I ask: Did it work?
“I did it, and it was spectacular, and it totally released me,” Costabile recounts, delighted all these years later. He did it three times that pilot season, and didn’t wind up booking anything, but it didn’t really matter. To pursue an acting career requires a special kind of delusion; delicious let him understand that fact without cheapening his work. “You know you're not going to cast you. You know you sucked. They know you sucked. You suck,” he says. “And then, in that moment, you would just be like, ‘Delicious.’ And it just lifts you out of the room. And it pours you through the door. And you're just like, that was the greatest experience I've ever had.”
“And that may have been the turning point of my career.”
We order a second drink, some fries, talk about our childhoods, and grow unusually drunk at a legendary restaurant on a weekday afternoon. It’s our time in the Skybox, basically.
The thing about the Skybox, though, is that you can’t go every night. Go too often and it ceases being special. Grow comfortable with your surroundings and risk losing the spark. Costabile is wary of too much Skybox time. “I don't want it to feel regular,” he says. “I want to feel like it's fucking fancy.”
But now, increasingly often, and despite his concern, Costabile finds himself in fancy places, meeting fancy people, and having fancy conversations. It’s been an adjustment.
Recently, Costabile found himself in Los Angeles again, this time for the premiere of the Netflix film The Dirt, in which he plays Motley Crue’s impossibly overburdened manager Doc McGhee, and to take a series of meetings about potential projects. All participants were effusive, like always. Lots of smiles. Compliments. “There were a bunch of people who would be like, ‘Well, we really want to put you in this movie, or this movie. We really want to work with you,’" Costabile remembers.
He was confused—this used to mean that they didn’t actually want to work with him, and yet the meetings had seemed to go so well. “I was just like, ‘Well, Maybe I've lost my mojo and I actually can't read these people anymore. Do they mean this? They really seem like they actually mean it,’” he says. “And I had to call my agents, and be like, ‘Did these people actually mean this? Because it seemed like they were just fucking sandbagging me.’"
His agents talked him down: everyone who told him they wanted him in their movie followed up with his agents. They really want him in their movies. “And I was like, ‘Oh, thank god,’” Costabile says.
It was, you could say, delicious.
Originally Appeared on GQ