The Central Park Guitar Man Readies for His Final Summer After 35 Years: ‘Let’s Embrace Every Song’

By Gus Saltonstall

David Ippolito says he was “given the gift of mediocrity.”

There is nothing mediocre, though, about his more than three-decade run of singing and playing guitar in Central Park.

Known as the “Guitar Man,” Ippolito has been performing on weekends at “The Hill” in Central Park, near West 75th Street, since 1992, to the delight of countless onlookers and participants.

Recently, Ippolito announced that this summer and fall would be his last, a final curtain call for parkgoers and longtime fans.

He is currently slated to play at The Hill on June 6, June 27, July 11, July 25, August 1, August 22, September 12, September 19, October 3, and October 17. He generally begins his sets around 1 and plays until 5:30 p.m.

On Thursday, West Side Rag had the chance to speak with Ippolito about his career in music, his time in Central Park, and why this would be his final year.

WSR: For someone who has never seen you perform in the park, how would you describe it?

Ippolito: The first thing I would say is that it is not a performance. It’s just a hangout and I happen to be the guy with the guitar. That’s probably one of the reasons for my longevity. They think I’m being self deprecating and cute when I say this, but I’m not. I was given the gift of mediocrity. That means it’s not going to get better than this with the songs that I write and the songs that I cover. This is what you’re getting. Tell me what you want to do next and we’ll do it. It’s that kind of non-performance aspect about it that has helped it live for 35 years.

Ippolito never arrives with a set list and sings a combination of covers and original songs.

WSR: How did you end up singing in Central Park the first time?

Ippolito: 36 years ago, I can say with confidence, I was a failure as a human being in every way that you can possibly be. I was homeless. I was a drunk. I own the whole thing. It was even a lot of fun, honestly. But it was fun until it wasn’t. The lights in the building were almost out, you know what I mean? That all changed at the end of 1991. By 1992, I wasn’t drinking or doing drugs anymore, and then I had the thought, maybe I can go make a little extra lunch money busking. I didn’t want to play in bars anymore. I didn’t want to play in clubs anymore. I was done with it. But, maybe I’ll just go out there with my guitar. I wasn’t really writing anything back then because I had nothing of importance to say to the world, but I thought, let me go make a little extra money. I went out to a spot in Central Park, opened a guitar case, started to play, and in about 10 minutes, I started to cry like a baby because I felt like such a loser. I just packed up my stuff and went home.

WSR: But, then you returned?

Ippolito: The next week, I must have been very late for something that I felt was important, because I was broke living in one room in Hell’s Kitchen with no furniture, but I was in a cab for some reason. The cab was cutting through Central Park and it stopped at a light. I see this spot where the main path went along the drive, but then a path went down and back up again, and I thought, maybe I can go down there and I won’t be in anyone’s face. I’ll be out of the way, and if people like the music they can come down this hill, and if they don’t, they can just keep walking.

So, the next weekend that’s the spot I went to. There were four or five people sitting there, and I asked if I could play a couple of songs, and they all went ‘yeah.’ The first song I played was a James Taylor tune. They clapped and I said, ‘please don’t do that,’ for two reasons: one I thought I didn’t deserve it, and the second, I thought that I had less of a chance of getting arrested if they were quiet.

But then something happened. In about an hour, there were probably 300 people sitting on The Hill, and every song was right, and everything out of my mouth was right, and they all clapped. And then, I thought I won’t get arrested if everybody is singing, so I asked them to sing along and everybody started singing. I played for four or five hours and at the end of it, people started coming up and asking questions. I was kind of digging the anonymity of the whole thing, but a guy came up to me and asked for my name. The next day, I got a phone call from a friend and he asked if I got The New York Times that day. The guy who asked me the question was named Jack Rosenthal, a senior editor with the Times. He had written this article about this spontaneous concert that happened in Central Park. It was my first time going there. That was all the affirmation I needed.

Until 1999, Ippolito performed in Central Park without a permit, but since then, has worked with the Parks Department and other city agencies to get the proper permitting for The Hill location.

WSR: What makes Central Park and The Hill such a special place for music?

Ippolito: I was born here. I’m the New Yorker you read about. New York and Central Park is what you know it is. In this way, I’m kind of an ambassador for this town. If someone knows that New York is old and it’s dirty, and it’s filled with fast-paced people, you’re absolutely right.

But, New York is also Florence during the Renaissance. It’s spotting Robert De Niro, it’s knowing King Kong climbed that sucker, it’s Broadway, it’s Lincoln Center, it’s Fred Astaire dancing in the dark, it’s romance, it’s Central Park! I’m constantly reminded of that. It’s magic and it’s romance.

WSR: Since you’ve been performing in Central Park for more than 30 years, I’m sure you have special relationships with longtime fans?

Ippolito: You can’t imagine it. I used to kid about it. At the 20-year mark, I used to say a pregnant woman who was out there, their kid is voting now. Over the years, I’ve gotten to watch people meet on The Hill, date on The Hill, fall in love, get married, and raise children. I’ve met globally famous people and become friends with them. The stories I could tell. It’s 35 years of life.

WSR: Any unexpected moments from the 35 years that have particularly stuck with you?

Ippolito: I’ll probably get emotional talking about it because I am a crier. When September 11 happened, I knew instantly I would never write a song about that day or that experience. But none of us knew where to put that in our hearts. That was on a Tuesday. That first week was really strange. There were no planes overhead. The bridges and tunnels were closed. But when the weekend rolled around, I just figured, I’ll be alone, but it’s what I do. So, I went to The Hill. There were maybe 10 people waiting. I was not going to do a memorial or sing patriotic songs, I was just going to do what I do. And then, all of a sudden one by one, and then two by 20, there might have been 1,000 people there. It felt like every single person who had ever been to The Hill, knew where they had to be that day.

I knew something important was happening and I knew I was right in the middle of it. I remember looking out at this crowd, this sea of faces, and I said, ‘if you’re anything like me, this week has been really weird, and you find yourself walking up the street, and you stop at the corner and you start crying, and then you get to the next corner and you’re suddenly filled with rage, and then the light turns green and you walk to the next corner and you think maybe pizza for lunch — and that might have been the toughest corner because we didn’t know what to do or how to feel.’

And, I said maybe that’s why you’re all here. So, I sang a song called ‘City Song.’ At the end of the song, maybe 1,000 people stood up on their feet and we just clapped and applauded for each other. It was remarkable. I still get emails from people all over the world that were there that day. That might have been the single most remarkable day that I’ve ever had with a guitar on my shoulder, and probably ever will.

WSR: And, how did you know and decide that this would be your final summer?

Ippolito: I’ve discovered that more than being a performer, I’m a creator. I get more of a kick from writing a song than I ever do at actually being on stage, and I have a lot of fun on stage. To answer the question, in my heart, I’m a playwright. For about the past seven or eight years, I’ve been getting really close to moving scripts of mine to seeing a stage. But, I did the math finally, if this is the 35th summer, that means I’ve been that ‘guitar man’ from Central Park for half of my natural life. I just turned 70 years old. I’m not kidding anybody. I don’t ever want to be the second baseman for the Yankees that held on too long. I don’t want to cross into desperation. I don’t know exactly what I’m going to do, but 35 years is a nice round number. Going back to the baseball analogy, there are the Derek Jeters who announce a final year and they have a whirlwind goodbye tour, so I thought let me do it the right way, and tell everybody this is it.

Let’s embrace every Saturday, let’s embrace every song, and then at the end, that’s it.

You can find out more about Ippolito and his upcoming performances on his website — HERE.

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