In this ShowbizU interview, Tony‑award‑winning playwright Joe DiPietro discusses how he discovered his passion for writing, the unconventional path he took without formal permission, and early milestones that validated his talent. He recounts winning a Scholastic Writing Award in high school, receiving his first paid commission for a Gershwin‑based show that later became the Broadway musical Nice Work If You Can Get It, and the creation and long Off‑Broadway run of I Love You, You're Perfect, Now Change. DiPietro reflects on the business realities of theater—production, marketing, and sustaining a commercial show—and emphasizes the importance of learning the trade. He credits Jamie Hammerstein, Oscar Hammerstein’s son, as his most influential mentor, describing how Hammerstein guided his rewriting process, audience listening, and career decisions. The conversation ends with DiPietro considering his own role as a mentor to emerging theater makers.
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What do you get when you have a Broadway professional and a camera crew? Long story short, you get a lot of cool info when you get Showbiz U Luminaries. This week we talked to Tony Award-winning writer Joe DiPietro, who won for Best Book and Score for the original musical Memphis. His other works include I Love You, You're Perfect, Now Change and the Tony-nominated musical Nice Work If You Can Get It. Let's talk about the journey of Joe. What was that moment where you said, I think I I want to do this. I want to write.
Oh, well, you know, the thing about being a writer is that no one gives you permission to do it. There's no degree that's going to lead to a magical career in writing. There's no path that every writer takes. Like, if you want to be a lawyer, you go to college, you go to law school, you take certain tests, and then you're a lawyer. So to be a writer, you have to really, I think, love to write. And I wrote for a long time and no one cared. I wrote at night. I worked in advertising. But whatever it was, I was young and I was stupid and I loved to do it and I thought, "I am just going to do it because I love it." And that's really sort of, I think, how the journey starts for every writer. You have to, you know, sit down and write it because you love it.
What were some of the first things that you wrote?
Well, it's funny, when I was in high— this is high school— when I was a junior, I was taking a creative writing class and a really wonderful teacher named Mrs. Milch who taught creative writing, and we had to do one of each type of discipline of writing. We had to write a poem, we had to write a short story, we had to write a short play. So, and then at the end of the year, there was something called the Scholastic Writing Awards, which was a national contest, Scholastic Magazine, it still exists. And we had to submit one of our pieces into one of these categories. So I got the best grade on my one-act play, which is probably about 10 pages long. And so I said, I got an A on this, I'm going to submit this one. And it wound up winning the contest in, like, you know, best dramatic script. I remember that was the moment it put it in the very back of my little mind saying, maybe you can do this someday. So it was a great encouragement for me.
What was the first time you got paid for your work?
Oh, that's an excellent question. The first time I got paid before I wrote anything, which was really— you essentially commissioned to write something— was a real thrill because that's the first time you really feel like Oh, they've seen some of my work. And I don't have to write a word, and I'm getting this little nice— it wasn't little, but it was a nice paycheck. And then, of course, the pressure becomes, well, I actually have to write it and deliver and not get fired, because I don't quite own this like I own my own stuff. So it was actually for— the first commission I ever had was for a Gershwin show, which eventually became Nice Work If You Can Get It, which played on Broadway for a year and a half. Last year, and that was about 10, 15 years before that. It was a long, long development process. I wrote it, it became something, then it became something else and something else, but that was the first time I got paid without writing, so that was a thrill. But probably the first time I ever really got produced was my show I Love You, You're Perfect, Now Change, which got produced at a sadly defunct theater called the American Stage Company, which was in Teaneck, New Jersey, not far from New York City, and also not far from where I grew up, and I had written these sketches about people who are single and dating, and the producer had seen them in this tiny, tiny little basement theater in New York, and they said, put music in it, this is a musical review. And the only musical review I had ever seen before was Ain't Misbehavin', which seemed very different, so I was like, I don't know what they really mean, musical review, it's sort of these sketches about dating and relationships and all that things. And so I met up with this writer/composer named Jimmy Roberts, who was a very talented composer, and he said, let's— because I really like your sketches— let's just put in a couple songs, see what happens. So he sort of guided me through that, and we did a reading, and suddenly, just in the reading with these like 3 or 4 new songs, it just opened it up. Like, I could feel like, oh, this is a whole new audience, it's a whole new way of telling a story, and it has this— the music has this emotional impact that the show didn't have without music. And then that show, through not probably all that long, probably maybe 2 or 3 years, got produced at American Stage Company, and then I actually got a paycheck. It wasn't a big paycheck. No, but it was a paycheck, and that is a thrilling moment for a writer because it's like, people paid money for these tickets to see my show, and now I'm actually making, you know, getting money for it.
And then that show obviously went on to have a Yes. A very long and successful run.
Yeah, I Love You Perfect Now Change went to two other theaters after the American Stage Company, and we opened in the Westside Theatre on West 43rd Street in New York City, which is probably the best Off-Broadway theatre in my opinion. And we came in, we got the theatre in August of 1996, I believe it was. And we got it in August because the theater owners didn't think we would last past, like, September, maybe if we got lucky, December. They were very nice about it, but that was just sort of what they told us later. So we got this prime real estate, and they actually had a show that was back— we'll call it backup— that was going to come in after we closed that was a big heralded hit out of town. It was, I think, a straight play. And then we wound up running for 12 years. So that was a good thing.
Not too bad for them either.
Not too— no, they were very happy and they, you know, it's funny because it was my first taste really of the business of theater. You know, as a writer, I'm like, I'm not really a businessman. What I love to do is, you know, sit down and, as I like to say, create arguments between fictional people. I mean, that's like what I do all day, which is weird, but that's what I love to do. And suddenly you have this commercial show running and making money and I was suddenly able to support myself, to write other things and I had some other opportunities arose. So it was a real heady and instructive time about, oh, you have to at some point, every artist of any type at some point should learn a bit about their business. What makes the business go? In my case, what makes a play get produced? What makes it run? What's marketing? You know, who are producers who know what they're doing? Like all those things. You know, it's just like any business, you know, the business changes, so you need to constantly keep up with it.
You talked about your, your second grade teacher, and I believe your sixth grade teacher, who were mentors. But who are some other mentors that have helped you get to where you are today?
Well, the biggest mentor in my life was Jamie Hammerstein, who was Oscar Hammerstein's youngest son. And Jamie was a very fine director, and he ran his father's organization, and he was also the first person who produced me, and he produced my first two shows in New York, I Love You, You're Perfect, Now Change and Over the River and Through the Woods. And Jamie was sort of the one, the first person of note who had said to me, you know, you can do this. He said, you might get some offers to go to LA and you might be tempted to go there because there's a lot of opportunities for people who, you know, write drama and comedy. He said, but you should stay in theater if you will love to do it, because you can do it. And Jamie really was also the person who told me how to rewrite, like how to listen to your audience, how to not listen to all of the noise that goes around when you have a new show and opinions and this and that. So he really taught me all that. So it was really Jamie, and he died very suddenly of a heart attack. That was several years ago. So yeah, but he really— I wouldn't be here without Jamie Hammerstein.
And are you finding yourself now being in that role for people?
Well, I love to talk to young people, and I love to take— there's a TDF organization called Open Doors, which I'm a mentor, where you take groups of high school kids, the same 8 high school kids, to 6 shows a year, and then afterwards you get together with them and talk about the themes and what it means and how it affects their lives. So that's been very gratifying. But yeah, no, I'd love to, like, you know, and I'll always, you know, read someone's script and give comments and stuff. But, you know, it's an interesting thing, you know, when you mentor someone and when you teach someone, the people who you really feel have a hunger for doing this, and, you know, they have a talent for it, but they have a hunger, and what that is and how they can sort of make their way is always fascinating. But yeah, no, I mean, I think you have to give back somehow. You have to get back somehow.
