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.