A Kraut, a Brazilian Guitar Player and a Guy from Jersey Walk into a Recording Studio…

Frank Sinatra spent much of the Sixties trying to maintain his commercial and popular relevance. As the decade wore on, that task became increasingly difficult in a country where the young Baby Boom generation had decided — quite wrongly — that a fiftyish white guy in a tuxedo had nothing to say to them.

Sinatra’s results were, at best, mixed. His 1969 cover of Simon and Garfunkel’s “Mrs. Robinson” was one of those timeless “what the hell was he thinking?” moments. In terms of quality and song choices, My Way was an uneven affair, but “Mrs. R” tipped the scales solidly toward the dreck side. S&G’s original lyric was about suburban hypocrisy and disillusionment. Sinatra sang it as an upbeat little ditty about a MILF he might have been fooling around with. “Where have you gone, Joe DiMaggio?” indeed — the most indelible line from the song is missing in Frank’s version.

Two years prior, Sinatra had at long last paired up with Duke Ellington for their first album together as Francis A & Edward K. What should have been magical — like the first Sinatra-Basie album a couple years prior — was mostly a waste of wax. “I Like The Sunrise” was the only Ellington piece on the whole album. The other cuts were contemporary songs of dubious worth. Worse, Sinatra reportedly had a cold during the recording sessions.

In between those two efforts, was Cycles, Sinatra’s take on pop-folk. I’ll spare you any further details than just that.

But Frank did hit gold during this same period, recording an album still considered among the very best of his seven-decade career.

It shouldn’t have worked. It should have been a disaster. It even sounds like the start of a joke: A Kraut, a Brazilian guitar player and a guy from Jersey walk into a recording studio…

…where, somehow, they made magic happen.

Just a few years before, jazz saxophone great Stan Getz went down to Brazil — and brought the bossa nova back home with him. Jazz Samba helped introduce American audiences to the sounds of Brazil — and we went nuts for it. Sinatra decided to make his try at it, by teaming up with the man who had invented the sound, Antonio Carlos Jobim. The arrangements — a mix of Jobim’s original songs and standards long familiar to Sinatra fans — would be handled by German composer Claus Ogerman.

Together they recorded Francis Albert Sinatra & Antonio Carlos Jobim, an album melancholy, lush and wrenching all at once. According to the liner notes, Sinatra himself said, “I haven’t sung that quiet since I had the laryngitis.”

Watch now, and listen, as Sinatra educates his longtime fans about this strange “new” music from Brazil. You might even learn a thing or two.