Two of John Pizzarelli’s greatest influences, Frank Sinatra and the bossa nova composer Antonio Carlos Jobim, joined forces in 1967 to present a softer, sultrier side of Sinatra on the heels of “That’s Life” and “Strangers in the Night.”

Half a century later, Pizzarelli is celebrating that unique gathering with his July 28 Concord Jazz release, Sinatra & Jobim @ 50.

Sinatraphiles consider the 1967 album Francis Albert Sinatra & Antonio Carlos Jobim one of Sinatra’s greatest, a meeting that found Frank in an out-of-character setting. Yet he delivered a commanding and understated performance over Jobim’s gentle rhythms and Claus Ogerman’s strings.

With Sinatra & Jobim @ 50, Pizzarelli pays tribute to those original recordings, enhancing that collection with two originals, Michael Frank’s ode to Jobim and songs that Sinatra and Jobim recorded at a 1969 session.

“Jobim was such a big influence on me in the 1980s—what I was hearing, then translating and what I was taking away from it,” John says. “A lot of what we did on this record, the medleys and the arrangements for the new songs, come out of what they did on their album and the influence they have had on my music.”

Jobim’s grandson, Daniel Jobim, is John’s duet partner on the Jobim classics Sinatra and Jobim recorded together: “Agua de Beber,” “Bonita,” “This Happy Madness (Estrada Branca)” and “Dindi,” plus a medley of “Meditation” and “Quiet Night of Quiet Stars.” They also cover the standards from the 1967 LP, “Baubles, Bangles & Beads” and a medley of “Change Partners” with Jobim’s “If You Never Come to Me” plus Cole Porter’s “I Concentrate on You,” which is paired with Jobim’s “Wave.”

Pizzarelli & company also perform Jobim’s “Two Kites,” Michael Frank’s

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