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When you make your living playing and singing classic songs that were popular decades ago, audiences can be surprised if you throw them a curve. Jazz guitarist and singer John Pizzarelli aims to do that at each show, stretching his repertoire with pop and rock songs and making them swing.


Pizzarelli is at home playing numbers from the Great American Songbook, show tunes and jazz standards his fans expect. But even though he often interprets music of a bygone era, he has no wish to be frozen in time.


"We've done Beach Boy songs in a jazz setting. We've done entire records of Beatles songs in a jazz setting," Pizzarelli said from his home in New York. "The new album is all songs from the '60s, '70s and '80s in a jazz setting, mixed in with jazz songs. So, I mean if you're not a jazz listener and you know the song 'I Feel Fine,' you're also hearing Lee Morgan's 'Sidewinder,' which you've never heard before."


The John Pizzarelli Quartet performs Wednesday and Thursday at the 

 Joining the guitarist on stage will be his brother Martin Pizzarelli on bass, Larry Fuller on piano and Tony Tedesco on drums.


Like his latest recording, "Double Exposure," the 52-year-old Pizzarelli is a link between the singer-songwriters of his generation and old-school jazz. But he's rooted in swing, a style he learned from his father, guitarist Bucky Pizzarelli.


As John Pizzarelli details in a new memoir, "World on a String," the family's home was magnet for his dad's famous friends, offering Bucky Pizzarelli's sons a front row seat to history, and a chance to sit in with legends.


"I've been around the greatest jazz musicians who ever walked the face of the earth, you know, Zoot Simms and Bennie Goodman, Joe Pass, Marshall Royal, Ray Brown, Milt Hinton, Clark Terry — and I've played with them," John Pizzarelli said. "This is the road I've decided to take and my job is to just play that music, like it's intended. When it's played like that it's not about 1947 to 1958. It's about just swinging hard and making great music."


Blessed with a father who had big connections in the jazz world, Pizzarelli wisely chose to stick to the family business. But he had to prove he had the goods, in the studio and on stage. For a while, his management banned him from playing with his dad, a prohibition later repealed.


"We could be selling salami or fixing pipes or something, you know, or selling cars," Pizzarelli said. "We like great music and playing it really well. I still am challenged on a constant basis by that 86-year-old guitar player and that's a great thing to have someone with that kind of spirit constantly listening to what you do and making suggestions or saying you played great. And, you know, if you get the thumbs up from him that's not so bad."


For many Pizzarelli fans, the place to be on weekends is near the radio when "from high atop Lexington Avenue" he and his wife, singer Jessica Molaskey, host "Radio Deluxe, program that blends music with storytelling and humor. The show keeps him connected with jazz fans, who have enjoy telling him what they like, and what they don't, much like the audiences he encounters in intimate settings like the Dakota.


Although some may not accept Pizzarelli's attempts to widen his musical boundaries, he sees it as a necessary step to expanding the audience to include younger people — that is, his age and younger.


"When you look at it, you'd have to figure somebody like Diana Krall, or even Tony Bennett or Natalie Cole all had Grammy-award winning monster records," Pizzarelli said. "They're not selling 8 million records to just people over 65, you know to that one generation, post-World-War-II-we-sat-in-our-parents-living rooms-when-they-played-Sinatra-records kind of group. The jazz people who are succeeding are finding ways to develop a new audience. Actually we all are."


Pizzarelli has developed and kept an audience on the strength of his playing and versatility and strong musical choices, ones that cover a variety of styles and tempos. His ability to sing hasn't hurt, especially because as his father suggested years ago, a guitarist can play only so many solos.


For all the travel, late nights and tough gigs a musician endures, Pizzarelli knows he has found something good.


"Listen, I have always said that I'm a lucky person that I get to play "I Got Rhythm" for a living," he said. "I've never really been told what to do, what to play. I just get hired to be me when I go to a city. I'm thrilled. It is a charmed life."

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When you make your living playing and singing classic songs that were popular decades ago, audiences can be surprised if you throw them a curve.

John Pizzarelli: expanding music with rhythm and swing

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