GREAT BARRINGTON — Jazz guitarist and vocalist John Pizzarelli brings his signature charm and musical expertise to the Mahaiwe Performing Arts Center.
Known for his tribute album "Dear Mr. Sinatra" and a lifetime and career steeped in jazz history, Pizzarelli blends classic Sinatra arrangements with fresh interpretations, accompanied by a 17-piece big band. "John Pizzarelli Big Band: Dear Mr. Sinatra" will take the Mahaiwe stage 8 p.m. Dec. 21. Tickets are $49 - $109 and can be purchased by calling the box office at 413-528-0100 or online at mahaiwe.org.
In this engaging conversation with Eagle Reels host Dalton Delan, Pizzarelli reflects on his rich musical heritage, collaborations with icons like Paul McCartney and James Taylor, and the healing power of music during personal loss, promising a night of surprises and timeless tunes.
DALTON DELAN: You're appearing at the Mahaiwe in Great Barrington on Dec. 21, soon after what would have been Frank Sinatra's 99th birthday. You opened for Sinatra in 1993, and you recorded a tribute album, “Dear Mr. Sinatra,” in 2006. Can you tell us about the show?
JOHN PIZZARELLI: We have a lot of things from our “Dear Mr. Sinatra” CD, a couple ofNelson Riddle arrangements, so it's a good evening of Sinatra music, or songs associated with Sinatra.
DELAN: Your father was swing guitarist Bucky Pizzarelli. You heard jazz from the cradle.
PIZZARELLI: He's on a few Sinatra records, and played with Sinatra on a couple of tours. Everything that I got, musically, started with my father pointing me in the direction of the Nat King Cole Trio and great music in general; great guitar playing that he did all the time was a big influence on me.
DELAN: You also played with Natalie Cole. Did you feel Nat King Cole’s spirit in the studio?
PIZZARELLI: My first time at Capitol Studios — they call it the tower that Nat built. All those Nat Cole records built that building. I was going to Studio B to record, out came Natalie Cole and she said, “What are you doing here? I saw you recording my father's song today, and I guess he couldn't be here. So there you were to say hello.” Talking about spirits, that's where that turned up.
DELAN: You have a lot of spirit guides. As a teenager, you managed to play with Benny Goodman.
PIZZARELLI: My father and I opened for Benny Goodman in 1980. We did six concerts. He was always at the house. Then I got to play with him one time in his living room.
DELAN: You do your own thing and you carry on some of these incredible influences. One whom everybody loves, and that I've been privileged to work with, is Paul McCartney. You played on his cheeky “Kisses on the Bottom” album. He's one of the nicest people I've ever worked with.
PIZZARELLI: That's what was so wonderful. Both he and James Taylor are just genuinely wonderful people. And you know why they're so famous, they're great musicians at the heart of everything.
DELAN: You co-produced “American Standard,” which won a Grammy in 2020 for James Taylor. You’ve played the Mahaiwe. Stockbridge was famously name-checked by him. Do you share any Berkshires connection?
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PIZZARELLI: Only from going up there so often, playing Tanglewood a number of times over the years, and recording there with James. Getting to go up to his barn and record there. To be at the top of the Berkshires, spending a lot of time and making music, and James telling funny stories, it was magical. So it's always nice to talk about James Taylor when the Berkshires are mentioned at the same time, knowing his affection for that part of the world and my affection for him.
DELAN: In 2020, when you won the Grammy with him, a week or so apart, you lost your parents. I'll tell you a James Taylor story of mine. We were in rehearsal for a White House show, just days after his mother died. I went up to him at the beginning of rehearsal. I was shocked that he made it to the rehearsal. And then he just cried. Music has gotten a number of us through a lot of fire and rain.
PIZZARELLI: April 1 and April 8, my father on April 1, my mother on April 8. My 60th birthday on April 6, which was supposed to be a big celebration. My getaway every day was to get out my guitar. I was trying to think of songs that my father never played, and to challenge myself to learn something different. What I did was, I started to learn Pat Metheny songs, my favorite ones. Pat had written me a condolence email. We started to talk. He said, “Oh, you're playing my music. Here's the music.” He emailed me all the music, and I recorded a record called “Better Days Ahead.” There's something about playing the guitar and saying, “I'm going to power through this as best I can,” learning the songs, thinking about my father saying to me, “Take your time in this section. What are you rushing for?” All the little things that happened from working with him for 40 years was coming back to me throughout that. So that was really how I got through all that.
DELAN: When Bob Newhart died this year, I thought back to 2002 when we gave him one of the early Mark Twain Prizes at the Kennedy Center, and you led the house band. You set the standard.
PIZZARELLI: It was just great to be in that room with everybody who was there. It was so remarkable. I remember the Smothers Brothers were backstage, talking to them. It’s amazing where music takes you, because the music brought you there. So those kinds of things, even looking back, are sort of, “Oh, that's right, we did that too.” It's sort of amazing.
DELAN: Any interesting projects coming up that we should know about, albums or anything else?
PIZZARELLI: There's a number of records that we've recorded that we’re hoping to finish, and lots of gigs after the beginning of the year. And my wife and I continue to do “Radio Deluxe,” which airs in the Berkshires.
DELAN: Do you like doing the radio show?
PIZZARELLI: The radio show is really fun. I'm at the cabin right now with Jessica. It's remarkable how many people have listened to the show all around. You can always tell the people who live up in the Berkshires, they hear the show up there, or in the Catskills, Minnesota, Los Angeles, Toronto. It's the little radio show that could. It's only 18 years old, so we gotta send it to college pretty soon.
DELAN: How big is your Big Band?
PIZZARELLI: Seventeen altogether. So it's a real live big band. It's an original show in so many ways, because it's not just the regular Sinatra arrangements. The band sounds so great in the Mahaiwe.
DELAN: Are you charting everything? Or are there charts from original songs that you're basing on?
PIZZARELLI: We have Quincy Jones's arrangement of “In the Wee Small Hours of the Morning,” which was only played on the road by Sinatra, never recorded. It would be nice to hear Nelson Riddle’s “I've Got You Under My Skin.” There's no other arrangement you'd want to hear of that.
DELAN: Sinatra recorded many Christmas songs. Any music of the season you're getting in there?
PIZZARELLI: We have some Christmas things, and we think of putting them in the show. We have fun with our concerts. It's a group of some of New York's best musicians coming up for the gig. It'll be great surprises.