We were lucky to catch up with David Ippolito recently and have shared our conversation below.

Alright, David thanks for taking the time to share your stories and insights with us today. We’d love to hear about a project that you’ve worked on that’s meant a lot to you.

At the risk of sounding trite, EVERY artistic project I’ve worked on has been meaningful in one way or another. Every script has a purpose. Every song has a purpose. I mean, if they didn’t… what’s the point of Creating?

As a songwriter, most often the purpose of the song is to let somebody know they’re not alone. Whether it’s something romantic, about Love, about heartbreak, whether it’s funny or whether it’s about any facet of the human experience, my lyrics should let a person know they’re not the only one who feels that way or felt that way.

As a playwright, of course, I’ve discovered each script has a more specific purpose… something it wants to say specifically to the audience.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Years ago I heard an expression: “If you hear hoof-beats coming up behind you, don’t think zebra.”

In my case… think zebra.

My career doesn’t look like a whole lot of other careers. And that depends on which career we’re talking about. I always tell people I feel like the luckiest man alive, for so many reasons. But for one, I’m a playwright who’s made a living for the past 30+ years as a fiercely independent songwriter. The story is way too long to cover it in a piece like this. But I’ve made a living as a singer/songwriter called “That Guitar Man from Central Park” since 1992. That’s 34 years ago. (See: www.thatguitarman.com)

The past 34 years have been a fun and fascinating ride. But 35 years ago I can say with confidence that I was a failure as a human being in just about every way possible. I was drunk, homeless, trying to do my body weight in cocaine, unemployable… hopeless… and the lights in the building were almost out. But that all changed at the end of 1991, and part of the road back included a day I decided to follow a whim to play music as a busker in Central Park… to make a little extra lunch money. That day was filled with magic. Every song felt right. Every thought I expressed landed on the people and in no time the crowd on this little hill by The Lake grew to several hundred. I played all afternoon, with people singing along and laughing… probably for 5 hours and went home with a guitar case overflowing with American currency. One of the people in the audience that day was a wonderful man and a brilliant writer named Jack Rosenthal, who unknown to me at the time, was a senior editor at The New York Times. Jack wrote a beautiful piece about this “spontaneous concert” and wonderfully, uniquely New York event that occurred in the middle of Central Park, and from that day on my Life as a songwriter began.

But through it all, I was lucky enough to realize for myself that I’m a firstly a “Creator” rather than a “performer”. So my writing remained my first passion. in 2025 I feel that it’s time for me to get off the stage and finally make the transition from a career as a singer/songwriter to a full time career as a playwright.

I’m currently sitting on several plays that some heavyweights in the arts have fallen in love with — people like John Lithgow, Alfred Molina, veteran Broadway directors Leonard Foglia and Scott Ellis and others.

Like I said… a fun and fascinating ride.

What’s the most rewarding aspect of being a creative in your experience?

It might sound trite or cliche, but the most rewarding thing about being a Creator… is the act of Creation. There was no play… and now there’s a play. There was no song… and now there’s a song. Feeling that the Creation is has touched someone’s heart, helped them think, opened their mind, or simply let them feel they’re not alone is a feeling that cannot be measured.

Part of the passion that drives me is the desire to have a seat at the table; to be able to jump-start conversations I believe the human race is ready to have. In the grand scheme of things, as a species, we’ve just recently crawled out of the primordial ooze. Humans have certainly evolved in extraordinary ways. But our understanding of Consciousness and the Universe is just beginning. Through the arts, I feel we get to explore humanity… while not taking our existence too seriously.

I love the “work”.

These days, in the 21st century, I mourn the abandonment of “craft”. For example… in songwriting, assonance has replaced rhyme. It’s become acceptable to merely go for the vowel sound to end a line rather than to work for the true rhyme. It’s lazy… but that’s where songwriting is these days.

The same hold true in the field of journalism. I was recently asked to do an “interview”. Instead of a journalist asking questions and constructing a narrative, I was asked to answer a series of questions,,, essentially writing the article for them. That’s not an “interview”. It’s the equivalent of being asked to write somebody’s college term paper.

It’s lazy. But it’s the 21st century and that’s just where we are.

I still admire the artists and others who show up to do the work.

Is there a particular goal or mission driving your creative journey?

I write plays about Life and Love and the human experience. I write songs about the same things. But I’ve dedicate a percentage of my work to hastening the arrival of the day when “religion” is nothing more than a curious memory for the human race. ALL of it.

Judaism, Christianity, Islam… ALL of it.

I, of course, understand where religion was born. I understand our ancient ancestors’ need to make sense of the unknowable. But it astounds me that it in 21st century so many around the world still put veracity in ancient texts about magic and fantasy. It’s beyond curious. It’s truly harmful. Just by it’s nature, it’s divisive. Part of my work as an artist is to shine the light of Reason on religion and its ugly second cousin… nationalism.

I’ve found that when I want to make a point or share a new idea, if I aim for the “intellect”, I run smack into a brick wall. But if I aim for the “heart”, I often find a secret passageway inside. But when I aim for the “funny bone”, I find a side-door that they didn’t know they left open.

Contact Info:

• Website: https://www.thatguitarman.com
• Facebook: https://www.facebook.com/david.thatguitarman
• Youtube: https://www.youtube.com/thatguitarman
• Other: TikTok — www.tiktok.com/@thatguitarman