Steve Lipman: The Singin' Dentist Balances Healing With Frank Sinatra


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When the Dream Academy sang, “Like Sinatra in a younger day," in their wind-swept '80s hit, “Life in a Northern Town," they could easily have been describing jazz singer Steve Lipman. Looking and sounding like Ol' Blue Eyes himself, Lipman mesmerizes with his warm crooning on his latest album, Ridin' the Beat. But what's fascinating about Lipman is that he balances a career in music with also being a dentist. Dubbing himself “The Singin' Dentist," he occupies a unique persona in the jazz world.

Q: When did you decide to become a singer?

A: Let’s just say that this was a transformation, a metamorphosis that took place over many years.

I was a pretty shy kid, quiet, kind of into my own little world. People who know me today don’t believe this but it’s true. I was a bit of an introvert, closed up tight but very independent. Being a singer was the farthest thing from my mind. Still, even in those days, I loved music. But it wasn’t the pop music being broadcast at that time. The Beatles were invading but they didn’t conquer this little guy. Musically, it seemed, I was born a generation too late. I tuned my ear to my mother’s albums. She had quite a varied collection of talented vocalists. It was soon clear that hands down, my favorite vocalist of all of them was Frank Sinatra. His sound was contagious to me. Early on I recall rummaging through her 78’s and finding this record titled “The Coffee Song.” I played that old disc until it couldn’t play anymore. I quickly learned every word of those lyrics. It was a crazy tune about coffee from Brazil of all things, but it had a wild and contagious beat.

Q: Growing up, what vocalists influenced you the most?

A: The interest in Sinatra’s music continued as I grew. I clearly remember when he released “That’s Life." It was a song was so cool, full of swagger and attitude. I loved it and sang it constantly. In high school I finally started to interact. Following my brother, I joined the drama club and after a few shows, actually landed leads in the musicals “Gypsy" and “Guys and Dolls." I became hooked on that glorious human connection, the sound of audience applause. It was like an addiction, a contagion that I couldn’t shake. It was a human relationship that I could truly understand.

Q: Where were you born, and where did you grow up?

A: I was born January 28, 1958 to two loving Jewish parents. Our home was a tiny apartment in Bridgeport, Connecticut. I was the second child of three boys. When I was one, we moved to a small house in Milford, Connecticut, the town where I ultimately grew up. We didn’t have much monetarily, but there was always plenty of love to go around.

Q: Did you receive any formal training to become a singer? How did you learn?

A: The year 1988 was a significant date in my timeline. That year, I purchased my own dental practice and became engaged to Shelley Rabinowitz. As a surprise, while we danced our “first dance” at our wedding, I sang to her Gershwin’s “Our Love is Here to Stay.” The music in our lives never stopped. We complemented each other. She exposed me to the marvels of classical music and the symphony. She turned me on to the wonders of Ella Fitzgerald, Billie Holiday, Duke Ellington, and Sarah Vaughan. I took her to more Frank Sinatra concerts than I can remember. I kept learning more and more songs. The lyrics kept running through my brain. I practiced whenever I could. I joined my synagogue choir and absorbed technique like a sponge. My choir instructor, Fern Cohen, gave me the only formal training I ever had. Everything else was self-taught. I performed any way I could. I became a regular understudy at my synagogue when they needed someone to chant services. When we went to weddings, somehow I always ended up doing a set of vocals with the band. I schlepped my wife to countless karaoke bars, wading through the endless line of intoxicated performers, patiently waiting my turn to hone my craft. Then it hit me. Newton’s apple finally hit me square in the head. My singing, my voice, was but just another musical instrument in an orchestra or band. The difference, however, was when you perform a song, you don’t just sing it. You let lyrics and melody take you over; so, in essence, you become one with the song. In other words, you “live” the song. That revelation changed me forever.

Q: How did you go from singing to dentistry?

A: Singing was a career path most people thought I heading. What they didn’t realize was that there was something else competing inside of me, drawing me in a different direction. I discovered I had a need to heal. This became an overwhelming preoccupation but achieving this was another story. My parents had limited resources. If I was going to go to college, I was going to have to put myself through. Any musical pursuit was going to have to be put on hold. I spent much of my free time and my summers, working and saving. I graduated from the University of Connecticut in 1980 with a B.S. in Biology and I was on Cloud 9 when I was accepted into the class of 1984 at the University Of Connecticut School Of Dental Medicine.

Yet the singer inside of me could not be contained. It was in my second year of dental school that for some reason I cannot remember, at holiday time, I decided to sing Irving Berlin’s “White Christmas” to my entire class. Crazy, yes, but believe it or not, it was well received. The following year, our class put on our own version of The Gong Show, which was a popular talent show running on television at the time. Rediscovering my Sinatra roots, I entered singing “New York, New York” with a chorus of ten behind me. We won the show. The following year, I won again this time singing “My Way." My interest in Sinatra’s music blossomed. I couldn’t get enough. Looking back, my attraction to those Count Basie/Quincy Jones arrangements meant something. It was a clear sign that there was going to be jazz in my future, but more about that later. By a stroke of luck, I managed to get a ticket to see Ol’ Blue Eyes live in Worcester, MA. What a night that was. Sinatra was on top of his game and sounded terrific. My mind was all music. The music was the sound of The Great American Songbook.

Q: When did you make the decision to begin recording albums?

A: The shtick was really starting to sound good. I started doing performances using background tracks at local fundraisers and the like. Each one was like a new discovery for me. Shelley would handle the equipment while I performed. We were a great team. At the end of one of our gigs, and I’ll never forget this, my wife came up to me and said, “Steve, you know the act is really going somewhere and you’re not getting any younger. Don’t you have that patient with a recording studio? Perhaps you better think about laying some of this stuff down."

I did have a patient who owned a recording studio. His name was Rod Warner. At his studio, The Green Olive Lounge in Coventry, I embarked on my first album, There’s a Song in my Heart. I also was introduced to a bassist named Dan Prindle. I can’t say enough about both these men. They each voluntarily took me under their wing, taught me the ropes, and opened my eyes to a wonderful future in music.

Q: Was jazz always your primary music of choice?

A: There’s a Song in my Heart was a continuation of what I had been performing at that time. My set list for those gigs looked like a collection of tribute songs to Sinatra done with high quality background tracks. For the album, we did our best to keep those arrangements and tried to create a full sound with the few studio musicians that we had. It wasn’t bad for a first effort. Still, musically, I was evolving. My ear was being drawn to a complementary but different genre of music. I now realized that this was the direction I needed to move forward with my music. That direction was jazz.

Q: How would you describe the creative evolution between the two records?

A: My second album had to be different. Although this project, Ridin' the Beat, was also going to hail form the Great American Songbook, I was intent on doing this with my own sound. I worked hours on end perfecting my vocals. Back at the Green Olive Lounge, my buddy Dan Prindle returned in a big way. As well as playing bass, he did all new arrangements for the songs I selected. He brought in an excellent jazz pianist, Stephen Page, and an accomplished drummer, Bryan Kelly. Dan took control of the rhythm section. For this recording, at the beginning, Rod brought the four of us into the studio to perform together and record some scratch tracks. This was necessary for the other studio musicians. After laying down “Moonlight in Vermont," Stephen looked up and said, “So when are we going out on the road?” Yes, it was obvious, the four of us clicked. We had a band. The Singin’ Dentist was born. The rest is history.

Have I abandoned my Sinatra roots? No, not really. In my eye he is still the great master, the mentor. To anyone who sees me perform, the connection is inescapable. That said, in my evolution as a vocalist, my sound has truly become my own. I’ve developed a tremendous love and appreciation for this genre of music. For the Singin’ Dentist, The Great American Songbook is the passion, and it’s all about jazz.

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