For most of his six decade career Sinatra had an unerring instinct for when to move on and take it to the next level. In 1942 he was the boy singer with one of the biggest bands in the country, but he wanted to go it alone, and in so doing ushered in the age of the star singer and the eclipse of the big bands. In the Fifties, he had plenty of hit singles but he had an urge to do something longer form, and so he invented the album as an art form. At the end of the decade he decided to be the first pop star to run his own major record company.

But by the mid-Sixties Sinatra seemed to be running out of things to move on to. He had always sung both standards and new songs. But he didn't seem to connect with the latest sounds the way he had with Styne & Cahn and Arlen & Mercer. What to do? Where to go? He found the answer - and a new collaborator - not in New York or Hollywood or Vegas, but in Rio de Janeiro:

Tall and tan and young and lovely

The Girl From Ipanema goes walking

And when she passes

Each one she passes

Goes 'Ahhhhhh...'

It was 1962 and they were just off the beach at Ipanema, in the Veloso bar: a musician-composer called Antonio Carlos Jobim, a poet-librettist called Vinícius de Moraes, working on a musical called Dirigível - or, in English, Blimp, which sounds oddly Lionel Bartish as a show title. It was about a space alien who lands in Rio during Carnaval. And they were stalled, as who wouldn't be? So they ordered another round of Brahma beers. And then the girl came walking, and they sat and marveled as she passed by, and, when she was gone, they turned back to the bar and wrote a song called "Menina que passa" - "The Girl Who Passes":

When she walks she's like a samba

That swings so cool and sways so gentle

That when she passes

Each one she passes

Goes 'Ahhhhhh...'

The girl was Helô - Heloísa Eneida Menezes Paes Pinto, who lived on the Rua Montenegro in Ipanema, in southern Rio. Tall and tan and young and lovely and emerald-eyed and wavy-haired, the girl from Ipanema came walking past the Veloso bar every day, and the patrons sighed. And sometimes she even came into the bar and bought a pack of cigarettes for her mother. And, when she exited, she was swinging so cool and swaying so gentle that the barflies would wolf-whistle ...but it sounds better if you say they were "Ah"-ing and "Oh"-ing. Helô was 19 years old and beautiful - ""the paradigm of the young Carioca," as Vinícius de Moraes would later write of her, "a golden teenage girl, a mixture of flower and mermaid, full of light and grace, the sight of whom is also sad, in that she carries with her, on her route to the sea, the feeling of youth that fades, of the beauty that is not ours alone - it is a gift of life in its beautiful and melancholic constant ebb and flow":

Oh

But I watch her so sadly

How

Can I tell her I love her?

Yes

I would give my heart gladly

But each day when she walks to the sea

She looks straight ahead, not at me...

Which is pretty much what she did that day. You say Helô, she says goodbye.

Contrary to legend, Jobim and Moraes didn't write the whole thing in the bar. That would have been too neat, even for an and-then-I-wrote anecdote. But they jotted down the gist of the music and text on two napkins - and then they parted and returned to their respective pads and put their respective napkins through some rewriting and polishing. And the girl from Ipanema started walking and never looked back. "It's the oldest story in the world," said Norman Gimbel, who would write the English lyrics. "The beautiful girl goes by, and men pop out of manholes and fall out of trees and are whistling and going nuts, and she just keeps going by. That's universal."

A half-century on, "The Girl From Ipanema" is surely the world's most sung pedestrian, yet is anything but a pedestrian song. It wasn't merely a hit, it wasn't just a smash, it was a phenomenon that spawned an industry. Today the Veloso bar is the Girl From Ipanema bar, not to be confused with the Girl From Ipanema boutique, owned by Helô, who's not so young but is still tall and tan and lovely and indeed a couple of years back posed for Playboy - with her daughter, who went on to marry the guy who hosts the Brazilian version of "The Apprentice". The street she once lived on, the Rua Montenegro, now bears the name of "The Girl"'s lyricist, the Rua Vinícius de Moraes. A giant facsimile of his original napkin bearing his original lyrics for "Garota de Ipanema" looms over the bar. Moraes and Jobim's most famous song singlehandedly created a global market for "bossa nova", which means no more or less than a "new beat". The beat was new, and had an interesting effect: In Frank's world, you generally did a song as a swinger or as a ballad, and if you added rhythm to the latter it tended to turn into the former. But bossa nova gave a love ballad just enough rhythm to let it shimmer and move and still be romantic and ballady. And "The Girl From Ipanema" was its ticket out of Brazil.

The first recording of "Garota de Ipanema" was by Pery Ribeiro. But the global breakthrough came courtesy of a record by the American tenor saxophonist Stan Getz. There are plenty of authentic Brazilians on the track, including Antonio Carlos Jobim himself playing the piano and the great João Gilberto on guitar - and singing, in Portuguese:

Olha que coisa mais linda

Mais cheia de graça

É ela menina

Que vem e que passa

Num doce balanço

A caminho do mar...

Toward the end of the session the producer Creed Taylor figured it might be smart to have the record include a chorus sung in English. Easier said than done. The only guy in the room who spoke English (Stan Getz) didn't sing. And the only guys who sang (Gilberto, Jobim) didn't speak English. So someone suggested Gilberto's wife Astrud, who'd strung along with her hubby on his trip to America and was sitting in the control room waiting to go shopping and sightseeing. Gilberto and Jobim objected strenuously on the grounds that she wasn't a singer and had never made a record. But Astrud understood just enough English to know what the words meant, and, being a game gal, agreed to give it a go:

Tall and tan and young and lovely

The Girl From Ipanema goes walking

And when she passes

Each one she passes

Goes 'Ahhhhhh...'

It was a brilliant notion. Mrs Gilberto's artless singing (no sustaining, no vibrato, no phrasing, no chantoosie technique at all) did more for the song than Billie or Ella - or Petula or Dionne - could ever have done: It's romantic but foreign; alluring and sensual, and yet distant and detached. Compared to how a great female vocalist would do it, the breathy, childlike Astrud is affectless - but in a sexy way. In other words, she is the Girl from Ipanema, as foreign and remote, as desirable and unattainable. She's vital to that record. Without it, a global hit would have been just another in-crowd West Coast jazz track.

As an amateur being given her first shot at studio singing, Astrud Gilberto was paid for her bazillion-selling vocal precisely zero dollars and zero cents - and that was just the way Stan Getz liked it. A few weeks later Creed Taylor returned from lunch to his office at Verve Records. His secretary Betsy told him that Stan Getz had called and urgently needed to talk to him. This was a few days after "Ipanema" had entered the charts. Creed assumed Stan was calling to make sure that Astrud got her fair share of the royalties. In fact, Stan was calling to make sure she got none.

Funny. But that was Stan Getz. When a rumor spread that he'd had heart surgery, Bob Brookmeyer said, "Did they put one in?" Etc.

Over half-a-century on, the Getz/Gilberto "Girl" remains an iconic record, one of those magical moments on which everything comes together - although back in Brazil some of the bossa boys thought Stan and his guys sounded a little square. But without Getz and "The Girl" I doubt bossa nova would have achieved mass appeal in the early Sixties. "Corcovado" and "Desafinado" are superb but feel somehow a little too special for the anglo pop trade without the wind of Ipanema beneath their wings. It was the perfect tune, and the perfect subject for it: a melody that wafts and a lady that sways to it.

That said, Mrs Gilberto's approach to the text was somewhat idiosyncratic:

Oh

But he watch her so sadly

How

Can he tell her he loves her?

Yes

He would give his heart gladly,

But each day when she walks to the sea

She looks straight ahead, not at he...

Presumably that's the singer's hasty but inventive solution to the problem of the final word: "She looks straight ahead, not at me" doesn't work because Astrud Gilberto has third-personed the song, and "She looks straight ahead, not at him" doesn't work because it doesn't rhyme. Whatever the reasoning, it drove Norman Gimbel, author of the English lyric, nuts. "I was tearing my hair out," he said. "It upset me no end."

On the other hand, Norman Gimbel's original lyric had a few other folks tearing their hair out. Gene Lees, who wrote English words for "Corcovado" ("Quiet Nights Of Quiet Stars") and many other Jobim tunes, prided himself on finding English words that nevertheless retain a Brazilian sensibility. It bothered him that, when the bossa craze hit America, Jobim's most successful composition was not Lees' "Quiet Nights" but Gimbel's "Girl From.." Norman Gimbel was a solid professional pop writer who could write anything - from Dean Martin's "Sway" to Roberta Flack's "Killing Me Softly With His Song" to TV's "Happy Days": Sinatra recorded four of Gimbel's Brazilian lyrics and two of his French ones, "I Will Wait For You" and "Watch What Happens". But in turning "Garota de Ipanema" into "The Girl From Ipanema" Gimbel threw out a big bunch of notes. In Portuguese:

Olha que coisa...

In English:

Tall and tan...

So a five-note opening phrase has been trimmed down to just three notes: "Tall and tan..." "He completely destroyed the swing," railed Gene Lees.

Oh, I don't know. And to be honest it's hard to believe "Ipanema" would ever have become the boffo bossa with a Lees text. And Gimbel used other tricks to give the song an off-kilter exotic quality: There are no rhymes in the main theme, only an identity ("passes"), and the climax of each section is not even a word but a sound ("Ah....").

"The Girl From Ipanema" traveled so far so fast that it went in nothing flat from being the trailblazer for a vibrant exciting new sound to an instantly recognizable shorthand for bland canned muzak: You'll recall the finale of The Blues Brothers when thousands of cops are pounding into Chicago's City Hall on the hunt for John Belushi and Dan Aykroyd, who are meanwhile glimpsed deadpan and inscrutable riding the elevator, accompanied by the omnipresent piped-in insipidness of that byword for elevator music, "The Girl From Ipanema". Or in Finding Nemo, the scene set in the dentist's waiting room accompanied by the acme of dentist's-waiting-room instrumental torpor, "The Girl From Ipanema". Or in Wayne's World 2, as Kim Basinger seduces Dana Carvey to the accompaniment of the ultimate in cheesy unfelt mood music, "The Girl From Ipanema".

But it's not bland and insipid and cheesy and torpid if you do it right. Sinatra was late getting to "The Girl From Ipanema" and by 1967 it could easily have been just another shrugged-off cover tune - one of those songs everyone sang, so why not (as Astrud would say) he? That's how Gimbel's "I Will Wait For You" came out, and Dr Zhivago's "Somewhere My Love", and "The Impossible Dream", and more than a few other Sinatra covers as the Sixties passed their midpoint. But once Frank had warmed to the idea, he really warmed to it. As Will Friedwald put it, if he was too late to be the guy who did the first bossa nova, then he'd be the guy who did the most bossa novas. A whole album of them. And he'd have the composer right there in the studio with him, playing guitar. And singing.

Which is how Frank Sinatra's list of male duet partners wound up reading: Bing Crosby, Sammy Davis Jr, Dean Martin ...and an eager baby-faced tousle-haired man-child from Rio de Janeiro. Unlike, say, Count Basie, Antonio Carlos Jobim was not an obvious Sinatra collaborator, and nor was the man Sinatra chose to arrange the Jobim material. Not Nelson Riddle, not Billy May, not Gordon Jenkins, not Don Costa, all of whom would have liked the project, but Claus Ogerman, a brilliant German arranger of great sensitivity who'd scored everything from Jobim's first American album to Lesley Gore's hit singles. As for the song that opened the album, Frank Sinatra - a man who thought nothing of playing around with Porter and Rodgers and injecting ring-a-ding Frankisms into Kern and Gershwin - was oddly deferential toward the young Tom Jobim:

Tall and tan and young and lovely

The Girl From Ipanema goes walking

And when she passes

Each one she passes

Goes "Ahhhhhhhh...."

Or maybe goes "Huh?", as in "What the hell are you thinking?" Sinatra swung and he delivered ballads that could be tender or harrowing. But he didn't really sing soft, or at any rate not since Close To You over a decade earlier. "I haven't sung this soft since I had the laryngitis," said Frank at the first Jobim session. The softness is vital: As the pianist George Shearing liked to point out, bossa nova isn't "Latin" - which is hard rhythmic and percussive. It's not even as bright and emphatic as the samba to which Gimbel's English lyric alludes. Softness is obligatory. In other words, to pull this off, Sinatra had to de-Sinatrafy himself to a remarkable degree. He trained for this album - not just in more sessions than usual with his pianist Bill Miller; he also eased up on the booze and the smokes, and went back to his old Dorsey-era vocal training - swimming laps underwater to extend his breathing and sweeten his tone. Softer, softer, softer: "If he sang any softer, he'd have to be lying on his back," wrote Stan Cornyn of the first session.

And yet somehow, as the song proceeded, it came out Sinatra anyway. Consider Frank's outro. If Gene Lees didn't like Norman Gimbel reducing five-note phrases to three-note phrases, what did he make of Sinatra throwing out half the remaining notes:

Tall

Tan

Young

Lovely

The Girl From Ipanema goes walking...

But Jobim and his guitar seem to appreciate it. And you realize that, for all the laryngitis talk, Sinatra's doing what he always does, just maybe a bit softer and suppler than he does with Cole Porter: He's exploring the song, identifying what matters to him in the story, and where he'd like to dig a little deeper. Jobim's guitar underlines the emphasis: "Tall. Tan. Young. Lovely." Without the smooth softening sway of all those "ands", the attributes of the passing girl seem to taunt and mock and frustrate even more than first time round: despite the name of his record company, with Frank a second chorus is rarely just a "reprise". But there's always hope, isn't there? And so:

...when she passes, I smile...

And he lifts the word, and it does, indeed, smile - but to no avail:

But she doesn't see... She just doesn't see...

And Jobim, his "vocal support" (as he's billed) a kind of ghostly co-vocalist and confessor, tries to tell him why:

Por causa do amor...

Because of love: You're in love with her, and so she's toying with you. Everyone else she's just passing, but you? She's passing you by, man - as Frank finally figures out:

She doesn't see me.

And so it ends not as a travelogue - like Astrud Gilberto's and many other versions, a vignette glimpsed through the window of a beachfront bar - but as a personal statement, an ache, a yearning for what Vinícius de Moraes called "the beauty that is not ours alone". Watch the performance Sinatra and Jobim give on Frank's TV special later that year and you get a sense of a respect for the song that survives all that Wayne's World and The Blues Brothers and the wedding singers and touch-tone hold-music can do to it.

And thus the most un-Sinatra-like project of the late Sixties earns a place among the great Sinatra albums - not a swinger, not a ballad set, but something all of its own. And proving that on the beaches of Rio an old dog can still learn a few new tricks.

~For an alternative Frank Hot 100, the Pundette is also counting down her Sinatra hit parade, and is up to hit sound 18: Cole Porter's "At Long Last Love". The Evil Blogger Lady is in less ring-a-ding-ding territory with Frank's version of the Lord's Prayer. And, speaking of singing softly, Bob Belvedere over at The Camp Of The Saints has a lovely celebration of some of young Frankie's best work with the Tommy Dorsey band.

~Mark himself sings just one line of "The Girl From Ipanema" halfway through his and Jessica's version of "Sweet Gingerbread Man". And don't forget, Steyn's original 1998 obituary of Frank, "The Voice", can be found in the anthology Mark Steyn From Head To Toe, while you can read the stories behind many other Sinatra songs in Mark Steyn's American Songbook. Personally autographed copies of both books are exclusively available from the SteynOnline bookstore.

SINATRA CENTURY

at SteynOnline

1) IT WAS A VERY GOOD YEAR

2) THE SONG IS YOU

3) HOME ON THE RANGE

4) AFTER YOU'VE GONE

5) IT HAD TO BE YOU

6) THE ONE I LOVE (BELONGS TO SOMEBODY ELSE)

7) LOVE'S BEEN GOOD TO ME

8) STARDUST

9) MY FUNNY VALENTINE

10) WHAT IS THIS THING CALLED LOVE?

11) CHICAGO

12) THE CONTINENTAL

13) ALL OF ME

14) WHEN YOUR LOVER HAS GONE

15) NIGHT AND DAY

16) I WON'T DANCE

17) I'VE GOT YOU UNDER MY SKIN

18) SOUTH OF THE BORDER

19) EAST OF THE SUN (AND WEST OF THE MOON)

20) ON THE ROAD TO MANDALAY

21) A FOGGY DAY (IN LONDON TOWN)

22) I GET A KICK OUT OF YOU

23) I'M A FOOL TO WANT YOU

24) OUR LOVE

25) ALL OR NOTHING AT ALL

26) I'LL NEVER SMILE AGAIN

27) FOOLS RUSH IN

28) MY ONE AND ONLY LOVE

29) EVERYTHING HAPPENS TO ME

30) I'LL BE SEEING YOU

31) THE WAY YOU LOOK TONIGHT

32) I'LL BE AROUND

33) THE NEARNESS OF YOU

34) PENNIES FROM HEAVEN

35) BLUES IN THE NIGHT

36) GUESS I'LL HANG MY TEARS OUT TO DRY

37) NANCY (WITH THE LAUGHING FACE)

38) SOMETHIN' STUPID

39) YOU MAKE ME FEEL SO YOUNG

40) I GET ALONG WITHOUT YOU VERY WELL (EXCEPT SOMETIMES)

41) SOLILOQUY

42) THE COFFEE SONG

43) I CONCENTRATE ON YOU

44) HOW ABOUT YOU?

45) THE HOUSE I LIVE IN

46) LUCK BE A LADY

47) WE'LL BE TOGETHER AGAIN

48) (AH, THE APPLE TREES) WHEN THE WORLD WAS YOUNG

49) I HAVE DREAMED

50) WHY TRY TO CHANGE ME NOW?

51) I'VE GOT THE WORLD ON A STRING

52) YOUNG AT HEART

53) THE GAL THAT GOT AWAY

54) BAUBLES, BANGLES AND BEADS

55) IN THE WEE SMALL HOURS OF THE MORNING

56) LEARNIN' THE BLUES

57) THE TENDER TRAP

58) STARS FELL ON ALABAMA

59) WITCHCRAFT

60) EBB TIDE

61) COME FLY WITH ME

62) ANGEL EYES

63) JUST IN TIME

64) I COVER THE WATERFRONT

65) NICE 'N' EASY

66) OL' MACDONALD

67) FLY ME TO THE MOON

68) AUTUMN LEAVES

69) IT'S ALL RIGHT WITH ME

70) MOONLIGHT IN VERMONT

71) COME RAIN OR COME SHINE

72) WE'LL GATHER LILACS

73) I THOUGHT ABOUT YOU

74) THE END OF A LOVE AFFAIR

75) THE BEST IS YET TO COME

76) THIS IS ALL I ASK

77) STRANGERS IN THE NIGHT

78) MOON LOVE

79) ME AND MY SHADOW