In 1964, when Getz and Gilberto ignited the bossa-nova craze across America, vocalists of all stripes—from Perry Como to Mel Tormé to Sarah Vaughan—quickly went Latin. Sinatra was a tad late to the party, teaming with bossa’s global exemplar for 1967’s Francis Albert Sinatra & Antônio Carlos Jobim. Speculation was that Sinatra, then at the height of his ring-a-ding-ding bravado, was ill suited to such delicate material.
In fact, he delivered what is arguably his finest album of the era, his exquisitely crafted readings shot through with soft sapience. He and Jobim reunited in ’69, but Sinatra was dissatisfied with his performances (most surfaced on 1971’s Sinatra & Company).