John Pizzarelli Recreates Sinatra/Jobim and Makes It New Again

The career of jazz guitarist and singer John Pizzarelli can seem like a puzzle, a set of almost-contradictions.

On the one hand, the core of his appeal is that he continues to sing and play “The Great American Songbook” associated with his father’s generation — his father being the estimable jazz guitarist Bucky Pizzarelli. On the other hand, Pizzarelli is a guitarist of choice for rock era musicians Paul McCartney and Ricki Lee Jones, at least when they lean toward jazz. He is both a tux-wearing cabaret artist at the Cafe Carlisle and a daring improviser capable of riveting the crowds at Birdland, Yoshi’s, or Blues Alley. There is even a certain tension in Pizzarelli’s personality: he is both a jokey ironist and a completely sincere raconteur.

These differences are perhaps best reconciled, musically, when Pizzarelli is playing bossa nova music, the lilting, jazz-rich style that came out of Brazil over 50 years ago. Effortlessly fusing Cole Porter sophistication with ’60s pop sunshine, bossa nova plays precisely to Pizzarelli’s two strongest modes. And it doesn’t hurt that Pizzarelli’s instrument is the key to bossa nova’s strummy sway and that Pizzarelli’s pastel singing style is ideally suited to this kind of music.

Sinatra & Jobim @ 50

This month brings the release of Pizzarelli’s second all-bossa record, following 2004’s Bossa Nova, on which he collaborated with several Brazilian musicians (including singer Daniel Jobim, the grandson of bossa nova’s Duke Ellington, Antonio Carlos Jobim) and arranger Don Sebesky. The new one, Sinatra & Jobim @ 50, is conceived as a celebration of the anniversary of the first bossa nova album by Pizzarelli’s fellow New Jerseyan, Frank Sinatra. Though Pizzarelli operates with sly wit rather than Sinatra swagger, he opened for the legend’s international tour in 1993. The connection is more than geographic.

“The idea first was to make a new bossa nova record,” says Pizzarelli to PopMatters. “I always knew I was going to revisit the style, but I was looking for a theme. I had a really successful tour in Brazil last year, and I had two runs at the Cafe Carlisle in New York with Daniel Jobim a couple years ago, so we had a lot of material. Then I looked around and saw that the anniversary of Francis Albert Sinatra and Antonio Carlos Jobim was coming up.”

That original 1967 collaboration remains a fascinating part of the Sinatra canon. The singers who were tackling bossa nova tended to be understated vocalists, breathy impressionists such as João Gilberto, and Sinatra’s band-singer bravado might easily have overwhelmed the material. Sinatra, however, knew what he was doing and was supremely adaptable — and the result was a wonderful album that found the middle ground between the style and the singer, based partly on astute Claus Ogerman arrangements. A footnote: the album was nominated for the Album of the Year Grammy but lost to Sgt. Pepper’s Lonely Heart’s Club Band.

Pizzarelli’s new one, however, does not reproduce the original, song for song. “I chose some material from the old record, but also some different songs, and a Michael Franks song, ‘Antonio’s Song’ that was written for Jobim, as well a couple original songs.

“The other big difference,” Pizzarelli adds, “is that Jobim wasn’t really singing on the original, he was just sort of scatting, and the only song he truly sang on was ‘The Girl from Ipanema’. I wanted Daniel more involved in the singing because we had the arrangements. I thought, let’s examine what it would be like if there was a real collaboration between the two voices. So we chose ‘Two Kites’, for example.”

“Two Kites” is a good example of how Pizzarelli breaks from the Sinatra formula in various ways. It is a feature for Daniel Jobim’s lead, with no guitar at all. Based on a piano vamp supported by hand percussion, the song sets Jobim’s vocals in call and response with background vocals by the Pizzarelli family — John, his wife Jessica Molasky, and their daughter Madeleine. “We had a limited budget here, so we used the voices on this tune and on other in the place of more elaborate arrangements,” Pizzarelli explains. “I like it better this way. It’s a little more personal and a little more ‘jazz’.”

Pizzarelli notes that there’s more “air” or free space on his record than on the Sinatra record. “I get to play some solos, and we have Harry Allen on tenor, who was obviously a great addition.” Though the record isn’t designed to evoke the classic Stan Getz bossa nova records of the 1960s, Allen’s creamy tone on “Bonita” and other tracks can’t help but tap into the listener’s memory of those intimate, small group outings.

Though Pizzarelli opened for Sinatra late in his career, the two artists don’t much sound alike. “When I do my Sinatra tribute material, there are always reviews that say, ‘He doesn’t sound like Sinatra.’ But that’s not the idea.”

That said, the Sinatra/Jobim record belies the notion that Sinatra was always a singer with brassy swagger. “We tend to forget what an intimate singer he was,” Pizzarelli agrees. “The bossa nova guys were so intimate, and I always loved that sound. Nat Cole had that sound too. Sinatra really captured that on his Jobim record. The guy knew what he was singing about, and he loved this music. I’ve seen the videos of him singing with Tom Jobim, and he knew exactly what he wanted to do with his music. Whether singing a ballad or in front of a big band or singing bossa nova, Sinatra always knew what he needed to do.

“I can’t do vocally what Sinatra did, but I can take his approach — to know what the lyrics mean and what I mean to do with the song. That’s what Sinatra has meant to me as a singer.”

Pizzarelli’s intent was to work within the spirit of collaboration that the first record represented. “The Sinatra record brought together great songwriting from Tom Jobim, from Cole Porter, and from Irving Berlin, but presented in a certain way.” And so here Pizzarelli has a similar mix of Jobim classics with American songbook standards as well as some original songs.

In several cases, Pizzarelli weaves together two different songs that come into conversation with each other. For example, he has Daniel Jobim sing “If You Never Come to Me”, a Brazilian song from the 1967 record, and then he brings in “Change Partners”, a Berlin song with a more American attitude toward romance. A similar approach is taken on “Meditation/Quiet Nights” and “I Concentrate on You/Wave”. “You also get two perspectives,” Pizzarelli adds, “when you hear Daniel comes in on the same song, like on ‘Dindi’ with a second take on the song”.

This is one of the ways that Pizzarelli keeps the sound fresh on this new record. He acknowledges that it can be a challenge for a bossa record not to sound like every lounge singer ever playing “The Girl from Ipanema”.

“The key to doing it in authentic ways is to have musicians with you who really play the music. We want to be honest to the music. I have these musicians around who can tell you when you’re really getting it. Guys like Duduka Dafonseca on drums and Helio Alves on piano are there to throw the red flag on you if you’re not being authentic. And they’ll do it.”

Beyond Bossa

While Sinatra & Jobim @ 50 maintains authenticity to Sinatra’s purpose and to the bossa nova aesthetic, Pizzarelli also finds ways to stretch its sound into his own era — a time when guitar-wielding singer-songwriters were a key part of the scene.

“The guitar and voice together is such an attractive thing to me,” Pizzarelli explains. “Whether it’s Peter Frampton, Harry Chapin, James Taylor, or João Gilberto just singing and playing. You can take a guitar, get up on the stage alone and play something.

“With bossa nova, it’s not just strumming. It’s bass note, chords, rhythm all at once. You can do it without needing anyone else. I heard João Gilberto’s Amoroso record from 1976 and I thought, Well, I gotta steal this. It becomes an obsession, and you just wanna do it all the time. It’s fun.”

Some of the tunes on Sinatra & Jobim @ 50 are more plainly up to date. Puzzler’s original “She’s So Sensitive” develops a bossa groove, but basically, it has the DNA or a classic mid-70s Paul Simon song.

“I wrote that song in 1984, and I’m particularly fond of it. Jessica and I were writing together some years ago, and she reworked the lyrics. I’ve had it for 23 years, and it contains many elements of what I was listening to back then.”

“Canto Casual” is also a Pizzarelli/Molasky original. Combining a clipped bossa groove, a Donald Fagan-esque verse melody, and a self-conscious Dave Frishberg-ian lyric, it grooves harder than anything on the recording. Each solo leans toward ecstasy, with the leader’s driving scat-guitar solo on the out-chorus ending the record with a feeling of forward motion. Similarly, “Antonio’s Song” weaves together bossa groove and ’70s songcraft, but this one is by the wonderful Michael Franks.

“Michael Franks is a hero of mine and one of the reasons I do what I do. Here was a guy with a similar voice writing these cool songs. There were some bossa novas, there were some swingin’ songs on the earlier records. One of the first records of his I liked,” Pizzarelli tells it, “was Sleeping Gypsy, before I got his classic The Art of Tea.

“My dad was on Franks’ Tiger in the Rain. He played the solo on ‘Hideaway’ and he played on the title track and on ‘Underneath the Apple Tree’. I got to meet him in the early 1980s and we were sort of friends for a while.”

“Antonio’s Song”, of course, is Franks’ explicit tribute to Jobim, and Pizzarelli mentions that his wife thought the album, perhaps, should be titled Antonio’s Songs. “I remembered at the 11th hour that Daniel and I had done it at the Cafe Carlyle, so it made it onto the record. The piano intro is the introduction that Claus Olgerman orchestrated on ‘Besame Mucho’ on the Amoroso record. Also, you can hear that we put a little reference to ‘The Girl from Ipanema’ in there as well, with Daniel singing ‘Bye, bye, bye, bye’ toward the end.”

Any chance that Pizzarelli might collaborate with Franks on a record in the future? The guitarist smiles at the thought of it. He has collaborated with a legendary guitarist named Bucky, singer Rosemary Clooney, songwriter McCartney, Mr. Sinatra, and now Jobim.

The unassuming New Jerseyan plays well with others.