Sinatra and Jobim, – Francis Albert Sinatra and Antonio Carlos Jobim (1967)

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NICK DERISO: Jobim’s bossa nova orchestrations — marked by feather-like rhythms and a freer song structure — provide the platform for Frank Sinatra’s most interesting late-period release.

“I haven’t sung so soft,” the belter once joked, “since I had the laryngitis.”

Stories of the way conductor Claus Ogerman struggled to get the sensual tempo just right for both men are legendary. This was Sinatra in his autumnal bravado, more inclined to ring-a-ding machismo than tender introspection. But he took these sessions seriously, having such great affection for the romantism that surrounded Jobim’s work. The Brazilian, meanwhile, brought his own drummer to add to the authentic vibe.

Sinatra and Jobim, it’s clear, listened on this day as much with their hearts as with their ears.

The result was an album of markedly rearranged standards from the American songbook — Cole Porter’s “I Concentrate On You” (given perhaps the most dramatic makeover), and Irving Berlin’s “Change Partners” — that also added new ones like the lilting “Dindi,” “Once I Loved” and “Quiet Nights of Quiet Stars” (embedded below).

In all, seven Jobim compositions are featured, including the timeless “Girl from Ipanema,” which launched the bossa nova craze in the 1950s — beginning with Jobim’s work on the 1959 film “Black Orpheus.” (A true collaboration, Sinatra sings in English, alternating with Jobim in Portuguese.) Through the next decade, a number of jazz notables incorporated elements of the relaxed, swinging style into their work, including Stan Getz, Ella Fitzgerald and Miles Davis.

Sinatra’s effort — filled as it is with so many pleasant surprises, and even more moments of still, lasting beauty — may be the most enchanting of them all.

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