At the beginning of his show Bad With Money, Ben Rimalower sings a bit from Judy Garland’s “I’d Like to Hate Myself in the Morning”, in which the legendary performer declared she would “raise a little hell tonight” and think about the repercussions later. Rimalower expresses that at first he thought the only thing he had in common with Judy was alcoholism, and yet he discovered that like the late singer, he also was up to his neck in debt. During the next hour or so, the charismatic performer tells us about the money problems that have plagued him all his life (his first words were a baby version of “buy me this”) and how as a kid, his life was divided into chapters associated with the before and after of his getting the latest object he desired.

With his energetic presence and adorable self-deprecation, I was almost expecting Rimalower to break into another Judy standard and express how “from the way that I feel, when that bell starts to peel, I would swear I was falling, swear I was falling - It's almost like being in love”, and yet the show takes a turn for the dark - in a humorous way - to make us realize how society has made us think discussing money is a bad thing. Bad With Money should be applauded not only for its entertainment value, but also for Rimalower’s courage. He puts a mirror to our faces and dares us not to look at ourselves and laugh along with him.

I had the chance to talk to Ben, who was kind enough to discuss the show’s themes, the works that inspired him and his love of Elaine Stritch.

The first thing I thought after I saw your show was “this is what straight people felt like while watching The Wolf of Wall Street!”

(Laughs) That’s a great compliment, thank you.

I didn’t really “get” what everyone liked about Wolf, but I really liked how you dealt with the same topics in your show. Do you feel in any way that your story will resonate more with other gay people for example?

I certainly would want people regardless of their sexual orientation to connect to the story, I hope I can resonate for a wider audience, but I think that there are lots of things about my story that clearly resonate to a gay audience. There’s also things that resonate to a Jewish audience, things that resonate with people who are into theater, I think there are so many cross sections of my story that bring people in.

I’m mostly asking this because gay culture nowadays always makes me think of yuppies in the ‘80s, people like Patrick Bateman from American Psycho who are obsessed with drugs, huge cars and trying so hard to be perfect, which makes them need obscene amounts of money.

Totally.

What other stories of addiction influenced you?

What I say in the show about loving recovery memoirs is very, very true. Things like Augusten Burroughs’ Dry, and the book Drinking: A Love Story by Caroline Knapp, were very influential not only for my show but for my own recovery as well. I guess the show about recovery that’s had the biggest effect on me was Elaine Stritch At Liberty.

Why was that?

First of all I’m obsessed with Elaine Stritch, and seeing that show when I was 26 was such a transformative experience for me. I think Elaine has a way of telling the truth while finding what’s funny.

You also hosted a tribute to her earlier this year, how was that?

It was such a wonderful night, we had such fabulous performers like Christine Ebersole and Beth Leavel and Edward Hibbert...it was a thrill just to be sharing the stage with them and I just had so much fun, and the audience was so wonderful and appreciative. I’m so grateful I got to have that experience.

I thought Elaine like Joan Rivers would be one of those people who would just never die. I wonder if we’re ever gonna get over losing them both so soon.

Maybe we never will, they’re a great loss, but they live on as we’ll always celebrate their work and be inspired their brilliance.

Since your show tells a story that’s still in process, do you find yourself making changes to the show every night?

No, we made changes over the last months of previews before the critics were coming, because I wanted to get it as good as possible, and then there are little differences from night to night because I like to stay in the moment and tell the story fresh to the audience, but the idea is for the script to be solid and tight, so it’s a piece of theater and not improv.

How do you adjust the tone based on audience reactions?

It changes a lot, my intention with the whole story is always the same, but from moment to moment it can be very different. It’s me in the room with a lot of people and even if I’m doing all the talking, there are a lot more of them than there are of me. It’s like playing catch, you can throw the ball, but you have to make sure the person catches it. It’s a conversation and the more I can stay present, emotionally tuned into what’s happening in the room, the better I can tell my story.

With your show basically being a confessional, do you find that people come up to you and tell you their stories?

Yeah a little bit, but that’s part of the fun of it. I’m always so interested in what people have to say.

Have you thought yet about who will replace you if you leave the show?

I’m nowhere near ready to do that yet (laughs) but it would be cool later.

In the past, when you’ve had other people play you, do you adjust the script to have the stories of whoever’s playing you included as well?

It’s a combination. We would make the adjustments necessary to make it believable, but at the end of the day, the tone they take will depend on their relationship to the material. Certainly with Robin de Jesus in Patti Issues it was a learning experience for me to see the text is only one part of what the theater performance is, Robin said my exact same words, but in a way I felt like he was telling me a story about his family.

Seeing the show made me laugh a lot, but then I read the script and it really broke my heart. Was this show hard to write?

At times yeah, it was difficult, because it’s a very naked expression of some of my darkest experiences and feelings. There are times when it makes me sad, and sometimes when it makes me happy. My telling these stories feels like a triumph.

Bad With Money plays every Thursday at The Duplex. For tickets and more information visit Ben Rimalower's official site.