Frank Sinatra Goes Bossa Nova With Antonio Carlos Jobim

Critics often dismiss Frank Sinatra as a mere ‘pop’ singer and don’t afford him the respect that they give to his contemporaries. He’s often accused of lacking technical vocal mastery and simply a singer who reworked a ‘formula’ over and over again. While Sinatra certainly knew what he liked and what worked for him, to belittle his artistry as a vocalist is unfair and displays a superficial knowledge of his body of work. Perhaps the finest example of his vocal excellence is his work with Brazilian guitarist Antonio Carlos Jobim.

Jobim is often credited with popularizing Bossa Nova music outside of Brazil. He worked with Sinatra on an album of samba tinged standards entitled Francis Albert Sinatra and Antonio Carlos Jobim. The work was a critical and commercial success, and Sinatra would hold Jobim in very high regard for the rest of his life”both as a musician and as a friend. After Jobim entered a semi-retirement in the 1970s and 1980s where he did little collaboration with other artists, Sinatra would often introduce his performances of Jobim songs live by remembering his Brazilian colleague in very fond terms or expressing the hope that the two men could work together in the future.

“Wave”, written by Jobim and arranged by Eumir Deodato, is among the best of all of the Sinatra/Jobim collaborations. It features some amazing vocal work by Sinatra, including perhaps the lowest notes he ever hit on a recording. It is said that for the rest of his life Sinatra would listen to “Wave” just to hear how good he sounds hitting the bass notes.

This song was to have been a featured track on a second collection of Sinatra/Jobim collaborations, but for some inexplicable reason it was never released as such. The story that has circulated over the years is that the Sinatra/Jobim album was all set to be released, and for some reason it was put on the back burner so that Reprise could release the concept album “Watertown” instead. As an artistic decision, it’s tough to fathom the rationale if this is the case. “Watertown” sold fewer copies than any other Sinatra release on Reprise, and to call it an “acquired taste” is being charitable. Another story is that Sinatra himself nixed the release because he didn’t like the cover art. The braintrust that came up with the idea of photographing the Chairman of the Board wearing a windbreaker and standing in front of a Greyhound bus could have been responsible for depriving the world of a second sublime collection of Sinatra with a bossa nova twist.

“Wave”, along with the majority of the songs intended for the “Sinatra/Jobim” album finally surfaced on “Sinatra and Company” in 1970. The “b” side is some of Sinatra’s ill-fated attempts to cover popular songs of the day (“Close To You”, It’s Not Easy Being Green”, “Leaving On A Jet Plane”). These are recordings that even the most rabid Sinatra fans consider among his most forgettable work, and a stark contrast to the masterful collaboration with Jobim on the album’s “A” side. “Wave” also appeared on the Reprise box set and of course of the “Complete Reprise Recordings” suitcase collection.

Will Friedwald, in his book on Sinatra’s music “Sinatra: The Song Is You” described the songs from the Sinatra/Jobim sessions as having “flexibility and delicacy, as if they could be blown about by a soft Brazilian breeze”. They remain among the most listenable and romantic work of Sinatra’s epic career, as well as representing perhaps his finest vocal effort.