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.
Enjoy.






Cultures and perception and leave long, funny tracks across our lives. When I was a kid I loved Sinatra on TV and movies but really had no use for his music. Astrud appeared on American TV when “The Girl From Ipanema” was a hit and Stan Getz played in a teens-in-a-winter-lodge movie.
A few years later I was a teen and a “freak”, Minneapolis slang for a hard, darker, sort of hippie. We listened to harder and darker music, took acid and raised hell. Like an entire generation, we threw out the baby with the bath water and everything changed in America based on an assumption that the previous generation were endemic conformists with no soul, addicted to weird double standards and clocks of kitties whose eyes and tail moved back and forth.
The early 80s saw me in Brazil, Rio mostly and I fell in love with the music of the day. But it wasn’t samba based for the most part because at that time Brazil was going through a golden age of what they termed MPB, Musica Popular Brasileira, or, in our terms, top 40. MPB was very much influenced by American popular music and, like our version, had its one-hit wonders, mostly, but also career names like Alcione, Simone and Gal Costa. I learned Portuguese with the help of a grammar book I still have and a long, lovely interlude in Rio followed by two more summer long stays in ’85 and ’88.
This was the era of the first Rock and Rio (1985) with a lot of heavy metal but also George Benson and James Taylor and which I attended. A nutty madhouse of giant crowds and unending rain and mud and a beautiful Dutch woman to share it with. Samba and Bossa Nova, though never far from the arrangements of the national pop music, was not popular in the larger sense and so it stayed through the end of that decade.
My next extended summer-long stays in 1999 and 2000 saw Rio as it always had been, the hip-hop generation no where to be seen and a country that musically was very comfortable in its own skin. Samba had made a huge comeback and there were more samba only radio stations that played a version also known as pagode, a mixture of mostly traditional samba with those traditional instruments but with more lyrical pop music that was very popular with teens; MPB was gone.
Again you had your one hit wonders together with other bands like Raca Negra, Alcione (still) Jorge Aragao and Revalacao. Culture and perception: in the late 1970s, before I embarked on several mammoth trips to the Third World, I often would sit and wonder what people did on a Friday or Saturday night in Rio or Dar-es-Salaam that was comparable to what we did as Americans.
Now, on the other side of those experiences, I’ve had some glimpse of that and what a hit song in the Brazilian summer of 1982-83 meant to a teen at that time and to me as well, my distorted version of “American Graffiti” and how a song could bring back a memory to someone in Rio of their youth as it happens with us in America.
At that time, in 2000, I became enamoured of Stan Getz and Antonio Carlos Jobim and a wave of nostalgia was also part and parcel of the Rio experience that summer.
The beginning of your video, Sinatra singing “Corcovado” with the English lyrics, reminded me of my enjoyment of that song in 2000 and the Portuguese lyric, “Da janela, ve-se o Corcovado, O Redentor, que lindo.” In the English version he sings “and a window looking on the mountains and the sea, how lovely” and in Portuguese it says you can look out that window onto the statue of Christ, the Redemptor, how lovely.
The difference to me was a nice one because at that time, staying with my girlfriend Silvana in Rio’s neighborhood of Humatia, I could indeed see Corcovado from her bedroom window as we lay there, a strong romantic vision for a freak from South Minneapolis raised listening to Grand Funk Railroad on a transistor radio coming down off acid on the front steps of my house as the sun rose and ended a long night trip.
I see now that those so-called “conformists” of the 50s were anything but; just look at the short science fiction stories that were out of this world innovative, acid trips without the acid, and also the plays and bare beginnings of rock and roll. Contrast that to the often natural but also often forced new-wave sensibilities that were done just to do it and the latter is the thing today, its original imperatives long gone.
And now the Left is itself a more calcified and conformist culture than its parents ever were and unpatriotic, unnostalgic and just as unconsciously bigoted and even racist. The difference is that there is no new generation to rescue us as our young people are the most politically correct of all as witness Arcade Fire and Lady Gaga with their constant harping about social justice where none is really needed; that dog stopped hunting long ago.
Culture and perception leave long, funny tracks across our lives and beautiful moments frozen in memory as well, often impelled by the strains of popular music. And they do put coffee in their coffee in Brazil, in tiny little cups while they stand off the street – cafezinhos.
Nice post. What a long strange trip it’s been, huh?
There is still innovative music out there. This band has quite a following in Brazil, playing Sao Paolo July 29… enjoy.
http://pitchfork.com/forkcast/16044-amanaemonesia/
Every now and then I break out that LP to mainly here the voice and sultry sound of Portuguese that Antonio Carlos Jobim brings to the record along with his portfolio of great melodic songs.
Frank was, as you said, on a choking string of trying to add his suave take on things like Jim Croce songs and this gem got him back on my turntable.
Ahhhhh!
I guess I’m more of a fan of “Strangers in the Night” and “Something Stupid” (with Nancy Sinatra) which were also recorded in the 1960s. What was wrong with those songs? They were “beau-tee-ful,” as they say in “Joisey.”
Sinatra reportedly hated “Strangers.”
Two great things from Brazil- Bossa Nova and Brazilian Jiu-jitsu.
I love Brazilian Samba…..LOVE IT…Gal Costa is the finest woman singer on the PLANET today….period…no arguments…. to hear Desifinado, in a full Samba, lush, sexual treatment….well……it makes you gasp….Please listen to some artists from this wild country. Maria Bethiana, Gal Costa, Jobim, Nasciemento, and the diva of all Samba, Astrud Gilberto…and the “Sinatra” of Brazil..Caetano Veloso…..amazing work…
I would like to correct the author on a serious but persistent misconception. Though Stan Getz was the the featured ‘star’ of the Jazz Samba album, the creative genius and main inspiration behind the album was guitarist Charlie Byrd. It was Charlie who was invited to travel and play in Brazil during a cultural goodwill tour sponsored by the Kennedy administration in 1961, during which time he studied and absorbed the wonderful Latin rhythms and melodies that heard there. He was completely enamoured by the music, and when he returned to the US, his wife that suggested that he contact Stan Getz to collaborate on the album. Charlie Byrd’s brilliant supporting guitar work and arrangements provided the solid backdrop for the now legendary versions of such memorable pieces as Desafinado and One Note Samba. Unfortunately, it was Stan Getz alone that won a Grammy for the performance, and Charlie even had to sue Verve to get the fees and royalties owed to him. All Getz had to do was come into the studio and play. Let us please give credit where credit is due, ie, to the vision and artistry of guitarist Charlie Byrd,for this great album that introduced the Brazilian sound to the North American public and launched the 1960′s Bossa Nova craze that changed jazz and pop music for ever after.
Thanks for the correction and explanation. I’ve filed that away so I won’t make the same mistake in the future.
none of this early stuff by Getz works without Astrud…..none of it….
Yes, yes, yes, it’s Sintatra’s finest album. And Ogermann is a genius. Check out Diana Krall’s “Live in Paris” sometime. http://www.amazon.com/Diana-Krall-Live-Paris/dp/B00005Y3ZM
Sinatra made a HUGE comeback in the 60′s with his “swing” albums especially those he recorded with Nelson Riddle. The article as written reveals a woeful lack of knowledge and appreciation of Sinatra’s ability to sing. He stands alone in a class of his own
I beg to differ, Kid R.
Sinatra glided effortlessly from Capitol to Reprise — his own label — as the Fifties gave way to the Sixties. He came out swinging (pun intended) with more collaborations with Nelson Riddle, and brand-new collaborations with Count Basie and “the kid,” Quincy Jones.
He had no need for any kind of “comeback.” Sinatra, unlike Elvis, never left the building.
What he did feel the need for, was “relevance.” That fact is obvious on the face of it, as he expanded from swing and saloon tunes, to… well… darn near everything else.
Some of those experiments worked, and gorgeously. Others, not so much.
But saying that does not in the slightest show a “lack of knowledge and appreciation of Sinatra’s ability to sing.”
As Sinatra aged, his voice developed a few weaknesses, but also new depths. (Literally in the later case, as he dropped pitch into an easy baritone as needed.) In fact, Sinatra was probably the first artist (the next was Tony Bennett) who learned to use the occasional weakness on purpose, to highlight some emotionally-wrenching phrase or word in a lyric. I’d suggest listening to his 1965 Live at the Sands performance of “It Was A Very Good Year” for a lovely example.
My problem with the recordings I complained about in the main article is: Sinatra’s sometimes-questionable music choices did nothing to showcase his uncontested and incomparable ability to sing popular American song.
His skills were all still there. The songs no longer always were.
“I am big; it’s the pictures that got small,” is the line I’m thinking of — only without Sunset Blvd.‘s tragic irony.
Now, if you’d like to discuss my lack of knowledge or appreciation for higher mathematics, or the uses of canned beets, I’m all ears. But I think I know my Frank Sinatra.
Sinatra and Count Basie, “Live at the Sands” is to me an almost perfect Sinatra experience: the songs, arrangements and light-hearted monologues tell a story of that era. “Fly Me to the Moon” ….. indeed.
Sinatra and Count Basie, “Live at the Sands” is to me an almost perfect Sinatra experience: the voice, the songs, arrangements and light-hearted monologues tell a story of that era. “Fly Me to the Moon” ….. indeed.
“As Sinatra aged, his voice developed a few weaknesses…”
Sure, age. But do you think his smoking had anything to do with it???
Geez, he’s even smoking in the video! Obviously a different time…
The writer has also overlooked Sinatras lame attempt at Rock N Roll in the late fifties while he was still with Capitol.
This period (1969) would see me graduate high school. My musical friends and I were aware of an appreciated Jobim, mostly when performed by others. We were also aware of and definitely did not appreciate Sinatra. That had to do as much (or more) with his public persona than the music. He just wasn’t cool, especially when compared with the rock bands of our generation. I would say the Sinatra as caricatured by Phil Hartman or Joe Piscopo on SNL was the perception we shared.
Years later, I was gradually led back into this material (Standards), initially by Nelson Riddle’s work with Linda Ronstadt (of all people!). I have a boxed set or two containing the Sinatra discography. My favorites have remained, “In the Wee Small Hours” and “… Only the Lonely”.
I have come to also appreciate Frank’s “style”. A sartorial style Mr. Green seems to share with Frank, at least as seen on Trifecta. A style Mr. Green could at least affect, with the possible addition of a grey Trilby with a large silk band. Think it over.
You do have me thinking!
Stephen . . . it’s a trap!
Yeah, the grey Tribble is sure to be a problem.
Sinatra certainly left a huge catalog of music to cull through. And to find and determine “his best” is tough, at best. For my particular palate, I still enjoy the continuity and song-to-song consistency of the “No One Cares” album he did with Gordon Jenkins. Ol’ Blue Eyes has lots to choose from but that one gets more time spent on my c.d. player than his others.
(uuh) Incidentally, I never heard his interpretation of Mrs. Robinson, but it sounds like that combination of artist and song was pretty toxic. Having said that, the recording that still brings snickers and frowns to my grill was Frank’s take of … “Bad LeRoy Brown.” The only thing truly bad about that version was that it was (indeed) BAD. And not in a Michael Jackson way.
Oh, wow. And Sinatra, of course, was a god to Bossa Nova musicians. From a strictly Brazilian point of view, the story of that recording began at a certain bar in Rio, with the waiter handing the phone to Jobim and saying, “It’s a call from the United States.” Frank Sinatra was on the other side of the line. Well, not exactly. It was Ray Gilbert first, to announce that The Voice would speak. Sinatra had the whole package figured out: Claus Ogerman, the songs, Tom Jobim on the guitar. Tom, a pianist, had only one request: a Brazilian drummer. How could it not have worked? Weeks later Sinatra and Jobim entered the studio, and once again Bossa Nova proved to be the perfect match for the best American music.
Thanks for the article. This is the soundtrack of the happiest moments of my childhood and youth, at least as I wish to remember them. Bossa Nova songs celebrate the instant — the passing-by beauty, the city seen through a plane window, the soap bubble, the breeze, the wave. Hence the melancholy. How beautiful. Good bye, young lovers.
Great post! The Chairman woulda said: “I hears ya been doin’ good tings…”
Thanks for the good read. Sinatra and Jobim collaborated twice and the results were pretty stellar. The same can’t be said for Andy Williams and the others who seemed to think Bossa Nova was fad that they could jump on to prolong their careers.
I’m working on a music doc which examines the influences of Brazilian music on non Brazilian artist. Sinatra, Quincy and Miles got it; Elvis and a a lot of others didn’t…
Thanks for posting the Sinatra/Jobim. Never enough Sinatra. Good on you.
You’re right to highlight the marvelous Sinatra/Jobim collaboration. The master’s touch with this material is magical.
Follow-up Bossa Nova recordings (arranged by Eumir Deodado) appear on a weird hybrid titled “Sinatra and Company” – including a delicious rendering of Jobim’s “Someone To Light Up My Life.”
The Ellington was never intended to be a songbook. Sinatra didn’t do songbook. The idea was for Sinatra vocals backed by the great instrumentalists of the Ellington Orchestra. Much the same approach he took when recording with the Basie Band.
For the Basie albums arrangements were by Neil Hefti and Quincy Jones. For the Ellington outing Sinatra tasked Billy May with charting the arrangements.
Basie and Sinatra were pals. Sinatra and Ellington were not. Ellington worried about Sinatra stealing his guys – Juan Tizol, Ben Webster and later Billy Strayhorn.
Still, the “Francis A/Edward K” has some marvelous moments. A wonderful reading of “Indian Summer” featuring a spine tingling good golly Johnny Hodges solo. A flag waving “Poor Butterfly.” A breakneck speed romping “Come Back To Me.”
My father’s absolute favorite music when I was growing up–Boss Nova and especially Antonio Carlos Jobim’s albums. I love this music too, it brings back great memories of listening to those big old LPs on the cabinet stereo as a child and singing and dancing to the music with my sisters!
I’m a rocker from way back (Beatles, Stones, the Who, Police, Van Halen, SRV) but when my mom died in ’89 I couldn’t listen to any of it; I found I couldn’t enjoy. I needed somthing more sombre and serious. I began to listen to more jazz and found a musical element I was ignorant of: phrasing. Of course Frank was the master of that and I now have 15-20 of his CDs. The Ronstadt/Riddle albums helped along the way.
The Sinatra/Jobim album album is my 2nd favorite after “Live with sextet in Paris” (awesome “Old Man River” and “Night and Day”)
I’m still a rocker but refer to Stevie Ray Vaughn as the Sinatra of guitarists; its all about the phrasing.
Great article!
Forgot to mention I also learned a lot about Gershwin, Cole Porter and Irving Berlin.
I hope you realize you’ve had me singing bossa nova all day.
And that the phrasing of Corcovado in Portuguese is a beast.
What strikes me watching the video is Sinatra’s economy. The only card available to an old man in a young man’s game.
Thanks, Stephen, for posting this. I did not know that Sinatra did a samba release with the great Jobim, as much as I’m a fan of his, as I truly love that Brazilian sound. It would set my Latin blood aflame, if I had any.
That is the most romantic music I’ve ever heard.
Hi, you really write in a way everyone – including me
– can@is able to understand, even if someone does not know very much with these things. But what exactly do you mean with your third paragraph? Frank