By Ernest Barteldes

The story of this album is the thing of legend, whether it is true or not. Antonio Carlos Jobim was at his local hangout in Rio (today named Garota de Ipanema) when the phone rang. It was an international phone call from Hollywood – none other than Frank Sinatra, who in those pre-cell phone days was trying to track the Brazilian composer because he felt it was the time for him to make a Bossa-Nova album.

Jobim had been enjoying international fame for a while now – he had collaborated with Stan Getz and Joao Gilberto on the landmark Getz/Gilberto album (which also launched the singing career of Astrud Gilberto), and had already recorded a number of records made for the international market (including The Composer of Desafinado Plays), and his songs were being covered by jazz giants like Ella Fitzerald, Oscar Peterson and Sarah Vaughan. Jobim immediately accepted the invitation, even though he was a bit annoyed by the fact that Sinatra wanted him to play guitar – and not piano – during the sessions.

A Sinatra bossa nova album raised immediate concerns among the bossa crowd. The singer was used to sing show tunes backed by a big, loud band – many feared that the Italian-American singer would somehow bastardize the genre by doing the songs in his own manner, as Brazilian journalist Ruy Castro wrote in Bossa Nova: The Story of the Brazilian Music That Seduced the World.

Sinatra, however, had done his homework. He recruited German producer Claus Ogerman, who had already worked with Jobim, to write the arrangements - he was adamant about making a real bossa nova album, having listened to recordings by Sylvia Telles and other singers; also brought in for the recording sessions was drummer Dom Um Romao, who was at the time playing in Chicago with Astrud Gilberto’s (right)band (she had since divorced Joao Gilberto, after a brief affair with Stan Getz)(left). The liners describe a moment in the sessions in which the trombonist played a note a bit too loud:

In addition to English-language versions of songs by Jobim, Sinatra also selected a couple of American standards adapted to bossa arrangements so critics wouldn’t call the album "Sinatra’s Latin Disc". The songs were Cole Porter’s "I Concentrate on You", "Baubles, Bangles and Beads Irving Berlin’s "Change Partners", a tune made famous by Fred Astaire. Some of those songs had already been recorded by Brazilian artists, so it was not a difficult transition.

The final result is quite positive: Sinatra sounds as subdued as he’d ever been, and in the few moments that he shares vocals with Jobim (on "The Girl from Ipanema" and "How Insensitive"), they sound as if they had been doing it for a while.

It should be noted that this record was recorded over three days during the winter of 1967 – most songs were recorded during a single take, and the final result was so positive that three years later Sinatra and Jobim reunited for yet another session, the lesser-known Sinatra & Company, which was produced by Eumir Deodato and Don Costa, and included several more bossa songs with some American pop songs.

Hearing the disc forty years later, one concludes that the music recorded over those sessions have stood the test of time; it is one of Sinatra’s most enjoyable discs, and is also a testament to the genius of Antonio Carlos Jobim.