By Glenn Rifkin

Though John Pizzarelli has written and recorded his own material, his specialty has always been embracing and interpreting the tunes of the giants and legends and making them his own.

Like most young aspiring musicians in New Jersey in the 1970s and ’80s, John Pizzarelli was transfixed by the likes of Bruce Springsteen and Billy Joel, who wrote and performed their own material. But, unlike most garageband wannabes, Pizzarelli had a more dynamic musical influence in his life, one who happened to live under the same roof. His father, Bucky Pizzarelli, was a legendary jazz guitarist who toured with many of the greats of the era, including Benny Goodman. Bucky was a longtime member of The Tonight Show Band (when Johnny Carson hosted the late night NBC fixture) and over the years he collaborated in the studio with a who’s who of stars, including Frank Sinatra, Anita Baker, Rosemary Clooney, Roberta Flack, Aretha Franklin, and Betty Carter, among others. The Great American Songbook was the soundtrack to John’s childhood and, when he picked up the guitar, he quickly realized that Springsteen might be out of his league. But there was a wide open niche for a young jazz guitarist who could interpret the classics for a new generation. An emerging virtuoso, he performed regularly as a teenager with his father, opening many shows for Goodman, and he found his muse in the music of Nat King Cole. He performed Cole’s hits and began recording his own albums in 1983.

Over four decades, Pizzarelli, 64, has emerged as a headliner, a guitarist, vocalist, and bandleader whose effortless and engaging humor and stage persona has enchanted audiences around the world. He has more than 20 solo albums to his credit and he has performed and collaborated on many more with his own pantheon of superstars. Though he has written and recorded his own material, his specialty has always been embracing and interpreting the tunes of the giants and legends and making them his own. Over the years, he has expanded his repertoire to include the music of Paul McCartney, Joni Mitchell, Antonio Carlos Jobim and, of course, Sinatra. In 2021, he won a Grammy as co-producer of James Taylor’s hit album, American Standard. He has taken his love of music into the broadcast booth, hosting a radio show “Radio Deluxe with John Pizzarelli” along with his wife, Broadway star Jessica Molaskey.

He spoke to Arts Fuse about his upcoming concert, “Swing Seven: Dear Mr. Sinatra“, at Groton Hill Music Center, February 21 at 8 p.m.

AF: You have a long-held affection for Frank Sinatra. Did you ever get a chance to play with him?

Pizzarelli: I opened for Sinatra on a tour in 1993. We did 18 concerts in Europe and the U.S. I relate a lot of the material for this show to that experience. But no, I never played with him. But that tour was amazing.

AF: How big an influence was he on your career?

Pizzarelli: Tremendous. I really started with Nat King Cole because Sinatra was too high a bar for me when I was 20. I was lucky to find the music of Nat Cole. But I got to spend a lot of time on a radio station in New York, WNEW-AM, with Jonathan Schwartz and Williams B. Williams. It was an education just listening to Schwartz talk about Sinatra and the material. My early 20s were spent listening to those people, being around that music, talking about the songs.

Guitarist, composer, and vocalist John Pizzarelli. Photo: courtesy of the artist

AF: You had a pretty good pedigree. Your dad was a jazz icon.

Pizzarelli: Yeah. I was in some pretty good jazz rooms. I got to see a lot of Benny Goodman concerts in the city. Goodman was a regular fixture in my father’s life. When he did a concert at a theater in Nanuet one night, he came over to our house afterwards. That was pretty wild. Bucky and I opened for Benny on a number of occasions. We opened for him at the Garden State Arts Center where I would subsequently open for Sinatra. It was quite special to have done that. I actually got to play with Goodman in his living room. It was me and my dad and Benny and we just played in his living room. Amazing.

AF: How much did your dad influence you?

Pizzarelli: He was such a good musician, and he was also a good road rat. He was the right guy to teach me everything. He knew how to get to an airport early, how to pack your bags, do all the things I didn’t know how to do. He was so well-respected. On my first record, My Blue Heaven, with my father and I, we had bassist Milt Hinton, Connie Kay, the drummer from the Modern Jazz Quartet, horn player Clark Terry, and Dave McKenna, that great Boston piano player. You can’t get those people unless they like my father. He’d say, “Can you come on down? Okay, great.” All those things were so important in learning what the business was supposed to be like. It was part of the foundation. And he led me to Nat King Cole, which was key.

AF: Your palette is full of musical color, from Sinatra to the Beatles. How did you figure out how and what you wanted to perform?

Pizzarelli: When I was starting out, a buddy of mine called me and asked me to accompany him at a gig. He asked me to sing some songs, but I didn’t have a repertoire. I was introduced to a singer that night who happened to do “Straighten Up and Fly Right,” a Nat Cole hit. I learned that song and, even though I’d still be performing at little rock and roll joints, I wanted to have my own voice. I got it through the Nat Cole material. That gave me songs I knew I could sing. It was a path no one was taking. Everybody was doing Sinatra or Tony Bennett, and I was doing Nat King Cole. I had a clear shot and that gave me a foundation for what I was going to do moving forward. At 24, I learned to keep my ears open. One thing I did have was good ears. So it saved me a lot.

AF: It was a time when rock and roll was so popular. What made you love jazz and that kind of music that wasn’t necessarily in vogue at the time?

Pizzarelli: It was also a renaissance of the Great American Songbook. At the beginning of the ’80s, you had those Linda Ronstadt records with Nelson Riddle. By the end of the decade, you had Harry Connick, Jr., Natalie Cole, Diana Krall, and others. It was a moneymaker for the record companies. I fit right in. There was always somebody looking for a poor man’s something. I had a ten-year period to have my own thing and I established myself and got it going.

AF: What can people expect from your Swing Seven show at Groton Hill Music?

Pizzarelli: We formed the Swing Seven for a gig at the Foxwoods Resort and Casino in Connecticut. I recorded the commercial “The Wonder of it All.” We put a group together with four horns and, over the years, we’ve taken a lot of our big band songs and pared them down to the four horns. It’s a cool little group, two saxophones, a trumpet and trombone. We focus on songs written for Sinatra, avoiding the big hits, but also doing such numbers as “Witchcraft”, “Wee Small Hours”, and “World on a String”, and a number of others familiar to Sinatra fans.

Glenn Rifkin is a veteran journalist and author who has covered business for many publications including the New York Times for nearly 35 years. He has written about music, film, theater, food and books for the Arts Fuse. His book Future Forward: Leadership Lessons from Patrick McGovern, the Visionary Who Circled the Globe and Built a Technology Media Empire was published by McGraw-Hill.