Bobby Underwood, the actor, singer and comedian, may be best-known for his work with the National Yiddish Theatre Folksbiene (he recently played Der Gradavoy in the Drama Desk Award-winning production of Fiddler on the Roof in Yiddish) but his most recent professional foray has been the legacy of satiric genius, Tom Lehrer. 
Born to a prominent Brooklyn family (his mother, Barbara, was New York’s first female Attorney General and the first female Acting Solicitor General of the United States) he was exposed to the works of satirists and comedians from childhood, which shaped his artistic identity.
His recent sold-out solo tribute show at City Winery, Thank You, Tom Lehrer, developed alongside musical director Zalmen Mlotek, Folksbiene’s Artistic Director, celebrates Lehrer, whom he cites as his primary comedic influence.
Thank You, Tom Lehrer returns to The Loft at City Winery this Monday, February 16 at 7 PM. For tickets, click here.
Tommy Batchelor, NiteLife Exchange (NLE) factotum, asks Bobby Underwood (BDU) Six Questions:
NLE: Thank You, Tom Lehrer has struck a chord across generations and returns to City Winery on February 16. What initially drew you to Lehrer’s work, and why did this feel like the right moment to bring his music and wit back to the stage?
BDU: When asked about the prescience of some of his seemingly topical lyrics, Tom said “predict the worst and they’ll hail you as a prophet.” Well, we’re in a pretty dark time here in 2026, and much of the darkness seems unprecedented, at least in this country. As you can see over time from watching things like The Daily Show, of which I’ve been a devotee for more than two decades, it’s harder and harder to make light of our current situation. Speaking only for myself, I take some comfort in the endurance of Tom’s songs. I imagine anyone with whom our show resonates feels similarly. I grew up listening to his albums—in fact I cannot remember a time when I did not know his name—so I think it’s always the right moment for a tribute to him. But that’s my best guess as to why this show feels almost necessary now.
NLE: You serve as host, narrator and performer in the show—guiding audiences through Lehrer’s life as much as his songs. How did you and Zalmen Mlotek shape the balance between storytelling, history and performance?
BDU: The storytelling is limited. There isn’t a tremendous amount known about his personal life, so mostly what we’ve done is set up who he was and how he got to be that way, and then we 
sprinkle in some anecdotes throughout the evening. But the show is mostly about his songs, along with his own comic introductions to his songs, which we adapted to fit in my voice. We run the gamut through his repertoire, from his first song, Fight Fiercely Harvard, written in 1945, to his last song, Hanukkah in Santa Monica, written in 1990 (long after most of his other songs were written).
NLE: Lehrer’s lyrics are famously sharp, political and sometimes deliberately offensive—even by mid-20th-century standards. How do you approach performing this material in 2026, when audiences may hear it through a very different cultural lens?
BDU: I warn them at the beginning of the show that most of his material is more than sixty years old. People weren’t offended by fewer things in the middle of the 20th century; they were offended by different things. There are things you can’t say now, but there were just as many (if not more) things you couldn’t say then—some of which would get you arrested, as my late father’s old friend Lenny Bruce knew all too well.
NLE: Your comedic style here is rooted in restraint—straightface delivery, precision, and timing—rath
er than overt punchlines. How does that approach serve Lehrer’s material, and how does it connect to your background in musical theater and comedy?
BDU: That was Tom’s own style and this show is a tribute to him. I’m not doing an impression of him, but I do try to deliver his material in the manner in which it was originally intended. Fortunately it comes rather naturally to me: our personalities are somewhat similar and, as I mentioned previously, I’ve been listening to his albums for my entire life.
NLE: The show has resonated deeply on a personal level, from your own childhood connection to Lehrer’s music to the story involving your mother’s Harvard thesis. How does that personal history inform the way you perform this work night after night?
BDU: Let me tell you, I wish I were performing his work night after night. Very little brings me more joy. To answer your question, I think it just gives me an extra feeling of connection to him. 
I never met the man in person, but as we were putting this show together, I realized that, aside from my parents, nobody had a greater impact on my sense of humor and how I see the world than Tom Lehrer. If you name any Jewish comedian or comic actor born before the mid-1950s, the odds are high that I’m a big fan. But nobody was as much of an influence on me.
NLE: You’ve worked across musical theater, Yiddish theater, film, stand-up and cabaret. Where do you see cabaret—and musical comedy more broadly—heading next, and how does Thank You, Tom Lehrer fit into your evolving artistic path?
BDU: I’m not an expert in Cabaret—though I love and have been in the musical! So I wouldn’t dare predict where cabaret is going next. I’m not even sure where it is right now. But as far as theatre, including musical theatre, is concerned, what I see is a world in which shows are increasingly hard to finance, and a lot of playwrights/composers/lyricists who have something to say can’t get their voices heard because there’s no one famous attached to their show, which is often what it takes to get a project off the ground these days. And artists’ voices are as crucial now as they have ever been.
As to my evolving artistic path, my answer to “what do you see yourself doing in five years?” has always been: “something interesting, I hope.” I don’t know what Thank You, Tom Lehrer will bring me, other than joy. People seem to like it and I’d love to keep doing it. If it leads to something else, I’m all ears.
