Steven Levenson is on a roll. As Americans waste away in windowless conference rooms, embezzling a few thousand here and there, living among foreclosure signs, lying to loved ones, to our government, even to that awkward crush from that intro writing class, this 29-year-old playwright has taken notice.

His Core Values, set over a weekend retreat at a wilting travel agency, premiered this spring at Ars Nova, where Levenson developed the piece as playwright-in-residence. And Roundabout Theater Company is currently staging his latest smart and powerful work, The Unavoidable Disappearance of Tom Durnin, about what a 57-year-old lawyer does after serving five years for financial misdeeds (for starters, crash on his son’s couch and work as a barista in the café at a Borders bookstore).

I caught up with Levenson while Core Values was up and running, and The Unavoidable Disappearance of Tom Durnin was in rehearsal for its summertime run, May 31 – August 25 at Roundabout’s Laura Pels Theatre.

Kathryn Walat (Rail): One thing that I noticed about your two plays is that so much is about the workplace and the effects of work and business in America. Is that something that you were thinking about consciously with these two projects, or was it fed by living in New York, or your experiences working?

Steven Levenson: There was a period where I was living off of commissions for about a year and a half, and then I went and got a day job again, and that was around the time when I started writing Core Values. And when you’re away from an office environment for a while and then you go back, all the weirdness of it hits you afresh. And it struck me that I was spending—that we all spend—most of our lives in these rooms doing things that we ostensibly don’t really care about.

Rail: Were you working in the office of a travel agency like in the play?

Levenson: No, it was an SAT tutoring company. But I didn’t tutor, I did admin—I was like a useless member of the team.

The setting of Core Values:

A conference room without windows. Silent and dark and shabbily carpeted. The color palette is puke: puke grays, puke greens, a gentle soothing puke brown conference table. Unused binders, obsolete promotional materials, and boxes of dead files have been stowed away in the dusty corners. On the wall, a poster, a cheeseball aerial portrait of an unblemished jewel-toned seascape: “Sandals!”

Levenson: With The Unavoidable Disappearance of Tom Durnin I started writing it amidst the financial meltdown. In earlier drafts that was a lot more pronounced, and then increasingly I became more interested in the characters and their relationships.

Rail: Were you thinking about Bernie Madoff?

Levenson: A little. The idea with this character Tom Durnin is that he’s not Bernie Madoff. Something that I find fascinating is all these guys in the late ’90s and the early 2000s who got caught and went to prison before everyone else got caught. Because the big guys, aside from the stray Bernie Madoff, by and large did not go to prison. A lot of them got promotions. I was interested in the idea of a small-time guy who wasn’t involved with millions of dollars but with tens of thousands of dollars. How devastating that is, on a small scale.

Rail: And the devastating effect it has on this family. It made me think about Death of a Salesman, especially with the father-son relationship between Tom and James.

Levenson: I love that play.

Rail: Do you think it’s time that we revisit some of the big questions Miller asks about America and work and the family?

Levenson: I do. I find Arthur Miller really fascinating, and I feel like he’s really dismissed lately as a playwright. We’re in this sort of Chekhov moment. When I think of Chekhov versus Ibsen, I put Arthur Miller in the Ibsen camp, the way they both foreground social commentary, versus basically being about these ephemeral life-moments.

I’m interested in plays about stuff. Real things. But then I’ve tried to write plays that come purely out of that place, and that doesn’t work out well. When I first started out playwriting, I was really into language and lyricism, I think to the detriment of character. And my writing has changed over the last however-many years, but I try to keep some of that. I don’t like just straight-up realism.

Rail: In terms of your attention to language, I love the linguistic hiccups in the scenes between James and Katie.

Levenson: It’s that awkward writing-class jargon. And the actors (Christopher Denham and Sarah Goldberg) are having a great time with that in rehearsal.

From The Unavoidable Disappearance of Tom Durnin:

JAMES: Oh, thanks. I thought your story was…
KATIE: Oh God. No. Thank you [...]But your story was, I loved your story.
JAMES: It’s actually—it’s more like a chapter. It’s from, I’m working on this novel, I guess.
KATIE: You’re writing a novel?
JAMES: That sounds so pretentious, doesn’t it?
KATIE: No, writing a novel, that’s amazing. [...]
JAMES: I mean, I just started. This was the first chapter. So. Literally just started. But. It might actually be more of a novella anyway, I think. [...] Yeah. Depending. So. On the scope.

Levenson: It’s just these two totally broken, messed-up people.

Rail: But there’s also a glimmer of hope in it. At the end of their very last scene together when James asks, “Did I screw everything up? I feel like I screwed everything up,” and Katie answers, “Not yet.”

Levenson: There were different drafts where there was a lot less hope, and we were left with nothing. But in a larger sense, the play is about whether people can change or not, if change is possible. And I’d like to think that it is. I need to think that it is. Without that, then why write plays? And sort of, why do anything? With James and Katie you can hold on to the hope that the past doesn’t have to dictate everything—the cycle can be broken—without being Pollyanna-ish about it.

Rail: Right, because you also present James as a liar—dumb little lies, but still.

Levenson: I like the idea that maybe James isn’t the reliable voice that we think he is at the beginning. Everyone in the play is lying at different points about different things, and it always comes back to bite them in the ass.

Rail: We see those lies come back again and again with James’s father Tom Durnin. What’s the effect of that on the audience?

Levenson: What’s so amazing about David Morse (playing Tom Durnin) is that I feel like I don’t lose sympathy for him ever. Even at the very end, in spite of everything he’s done, there’s such decency about him as a person that you want to believe him, and you want him to be okay. And David really captures that.

TOM: I could have shown things to the prosecutors, Chris. I could have cut my sentence in half. I could have walked away with a slap on the wrist. [...] I could have put you and Glen and Mark and Barry and Vanessa, all of you, I could have put every single one of you in jail.
CHRIS: Then why didn’t you, Tom?
TOM: Loyalty, Chris. That’s why. Loyalty. [...] And if you don’t have loyalty, then what do you have? Nothing.

Levenson: Throughout the rehearsal process the actors have been great about asking smart questions. Something that Chris Denham, who plays James, came in with a lot of thoughts on is making sure that you feel like James has been damaged for a long time, and that his wife leaving him is a symptom of that, part of the whole thing, rather than the cause. Everything in James’s life, including that, is really just an extended effect of his father’s betrayal.

Rail: For me when James talks about how his life imploded, it brought it back to the father-son relationship even more.

JAMES: You think this is what I wanted? You think this is how I pictured my life going? Selling stethoscopes, living alone in this house in the middle of nowhere, in this shitty subdivison? You think this was the plan, Dad? I wanted to do something with my life. I wanted to actually do something, Dad.

Levenson: Totally. His trust in the world is broken.

Rail: Do you think our trust in the world has been broken a little bit, with all this financial stuff that’s been happening?

Levenson: Absolutely. I feel like there is no baseline trust in institutions anymore. And that’s obviously not an original thing to say. With this stuff that’s happening right now with the I.R.S. or the A.P., people are pretending to be surprised and outraged, but everybody sort of expects that, don’t they? But at the same time I don’t want to be cynical.

Rail: I think the endings of your plays are not cynical. I love the stage direction at the end of Core Values, in the conference room of the travel agency.

Richard is alone. He slowly puts on his coat and gets his bag. He stops. He stands there. He looks at the mess around him: tropical streamers, half-empty water bottles, half-eaten bagels, coffee cups, legal pads, binders, napkins, the detritus of the weekend. He considers the next 30 years. For a moment it’s all too much and the force of it nearly takes the breath out of him. But then it passes. He shuts off the lights and goes home. End of play.

Levenson: That moment has changed a lot in different drafts. And then you get with an actor in rehearsal and it’s like: what does it mean, how do you do that?

Rail: Well it means he’s not going home to kill himself, which at a couple of moments in the play I thought might happen.

Levenson: I want to feel like at the end of that play he’s going to put all his money into the company and keep it going for as long as possible, whether that’s good or not. He’s not giving up—and maybe you want him to give up, and probably he should give up—but he’s not going to until the very end.

Rail: That kind of feels like the theater to me.

Levenson: Very true. It’s like, what else can we do? It’s like that Beckett line.

Rail: “You must go on . . . I can’t go on . . . I’ll go on.”

Levenson: And I love that! The twisted optimism of that. That’s sort of that ending for me.

Steven Levenson’s The Unavoidable Disappearance of Tom Durnin runs through August 25 at Roundabout Theatre Company’s Laura Pels Theatre (111 West 46th Street, Manhattan). For tickets and further info, visit www.roundabouttheatre.org or call 212-719-1300.