© 2024 254 North Front Street, Suite 300, Wilmington, NC 28401 | 910.343.1640
News Classical 91.3 Wilmington 92.7 Wilmington 96.7 Southport
Play Live Radio
Next Up:
0:00 0:00
Available On Air Stations

Celebrating Sinatra's Centennial: A Biographer Reflects On Ol' Blue Eyes


This is FRESH AIR. I'm Terry Gross.


GROSS: Tomorrow marks the centennial of Frank Sinatra's birth.


FRANK SINATRA: (Singing) It was just one of those things, just one of those crazy flings, one of those bells that now and then rings, just one of those things. It was just...

GROSS: Sinatra was born on December 12, 1915 in Hoboken, N.J. We're going to listen back to one of our favorite interviews about Sinatra with Will Friedwald, who's written a number of definitive books about singers and popular song, including "Sinatra! The Song Is You: A Singer's Art," which won an ASCAP Deems Taylor Award for excellence in music criticism. It would be easy for a biography of Sinatra to let his celebrity, his love affairs and his rat pack adventures overshadow his voice, but that's exactly what Will Friedwald avoided. He wrote a musical biography, focusing on Sinatra's voice and his recordings. Although Friedwald wasn't able to interview Sinatra, he did speak to arrangers and musicians who worked closely with him. Our interview was recorded in 1997 when the biography was published in paperback. Sinatra started his recording career with the Harry James Orchestra in 1939. Let's begin with their most celebrated recording, "All Or Nothing At All."


SINATRA: (Singing) All or nothing at all, half a love never appealed to me. If your heart never could yield to me, then I'd rather have nothing at all. All...


GROSS: Will Friedwald, welcome to FRESH AIR. And let me start by asking you why this recording is a defining moment musically for Frank Sinatra.

WILL FRIEDWALD: Well, to me, it's interesting because one of the things you constantly hear about Sinatra, even from Sinatra himself, is that he learned a lot of his technique, particularly in terms of breath control, he learned a lot of that stuff from Tommy Dorsey. And it's interesting to see him here in August 1939, which is, like, four whole months before he even joined Tommy Dorsey, here he is doing a lot of that stuff way, way early, way, way before he even met Dorsey. And it just goes to show that this was something that Dorsey, of course, encouraged and nurtured but that he didn't need Dorsey to introduce him to it. I mean, he was already doing that stuff way, way back in the early part of his career, and...

GROSS: What's the stuff you're talking about, the kind of breath control that he has?

FRIEDWALD: Well, that long, basically, holding notes, I mean, that sort of long legato style, which you can hear throughout "All Or Nothing At All." And this is, in a sense, the original element, the original Sinatra breakthrough. This is what made him different from Crosby. This is what makes him different from any other pop singer or jazz singer of the 1930s, the way he holds those notes for dramatic emphasis, for musical emphasis, to contain the thought of a phrase all, you know, within a certain musical boundary, which is what no other singer was doing at that time. And then to hear him doing it before Dorsey, who he always said was the one who taught it to him, it's really quite remarkable.

GROSS: Now the amazing thing is that this wonderful recording didn't sell in 1940 when it was first released. But then it was re-released - what? - three or four years later, and it sold a million. What was the difference there?

FRIEDWALD: The Harry James Orchestra was sort of a B band in 1939. They were brand new, they had not caught on yet, they did not have any big hits, and Harry James had not done all the movies that he would later do. And they were just kind of a struggling operation during the time that Sinatra was in the band. In fact, when Sinatra broke through, you know, at the end of 1942, the beginning of 1943, people, of course, remembered that he had been with Dorsey, but they completely forgot about the Sinatra-Harry James relationship. You know, most of the bobby soxers and the Sinatra fans at that time had no idea that he had been with James. And when they reissued that record, it was kind of an odd circumstance in that they re-issued it in the middle of a 1942-44 musician strike. And so if you really wanted to hear what Sinatra was doing at the Paramount - it was going, you know, driving all the girls crazy at the Paramount - there really was no evidence on records. The only records that he did make were with these kind of a cappella choirs. So the best representation of what Sinatra sounded like was this 4-year-old record.

GROSS: Before Sinatra became a solo singer, before he was out on his own, he was with Harry James and then with Tommy Dorsey. Why did he leave the bands to go out on his own?

FRIEDWALD: It's interesting, that. I was talking to a press agent named Gary Stewart who knew Sinatra from the very early period. And he remembered a conversation he had with Sinatra circa late-'42, which is after Dorsey and before the sort of bobby-soxer breakthrough that he had at the end of that year. And he said that Sinatra was talking to him about his future plans and that he knew exactly everything he wanted to do, including the whole multimedia career thing, which was to have a radio show, which was to make recordings and even to go into pictures. And he said that Sinatra had the aspiration to win an Academy Award as early as 1942, which was before he'd even starred in a picture. Mitch Miller said the same thing to me in that Sinatra had this kind of whole career plan all mapped out. He really knew where he wanted to be, where he wanted to go. And he knew that singing with the big bands, as lucrative as it was, and as easy on him as it was - I mean, it certainly was a very responsibility-free life. And when he first left, he had a big - a payroll of his own to meet and he had a whole bunch of responsibilities that he never had just a few months earlier. But he sought them all just because he knew that was the next step. And he also knew that - and again, this is something he said in interviews - he knew that if he were ever going to make it as a solo singer, he had to do it the sooner the better become there were some formidably great singers in the big bands. He was really worried about Dick Haymes, he was worried about Bob Eberly, and he was worried about Perry Como. And he figured the sooner he could get out on his own, the better it would be for him because there might not be a position - that was the term he used - there might not be a position for him if he didn't get out as soon as he could. Sinatra really does become the first singer established by the big bands to leave the big bands and start something on his own. And he really launches that whole avalanche that kind of defines postwar pop, which is the phenomenon of the solo singer who leaves the big bands and has hits on his own. And Sinatra's really the role model for that whole generation.

GROSS: Why was that hard to do? Why was it so unusual to do?

FRIEDWALD: Well, the big bands were so entrenched. I mean, basically that was pop music. Pop music was, you know, 16 men and a guy waving a stick. I mean, that's what people danced to. And it was more of a dancing culture at that point than a listening culture. And the big band leaders were heroes. People like Benny Goodman and Harry James really were matinee idols. I mean, we can look back and say yes, they were virtuoso musicians and, you know, they were also great jazz men, but at the time they were just thought of as pop stars.

GROSS: Well, as you said, you know, when Sinatra was starting to record on his own, the musicians strike was in effect, and there was a recording ban. You couldn't record with musicians because they were on strike. So some singers were making a cappella records. And there were these, like, choruses of voices instead of a band behind them. And you write that Sinatra held out as long as he could. He kind of held out until the last minute, but he finally capitulated toward the end of the strike and started recording these a cappella records. What do you think of these records?

FRIEDWALD: Well, they have a kind of charm all their own. I don't think they're representative of what Sinatra was doing because we know from air checks that, you know, the stuff with orchestras was much more lush and languorous and much more representative. It's interesting that Sinatra always said that he held out, and I don't doubt that he's sincere, but he made more those a cappella records than anybody. He made, like, nine or 10 titles, and I don't think anyone else made more than three or four. Bing Crosby only made four, as far as I know of. But it really was not a viable means for him to work in. In fact, as early as 19 - like, September or October '42, right after he left Dorsey, some of the press reported he was thinking of making those kinds of records, but he didn't actually do it until June of '43.

GROSS: Let's hear one of those a cappella records that he made. And this is close to you, which is also, I think, the first recording that he did for Columbia as a solo singer.

FRIEDWALD: Right, this the first - this essentially is the first Sinatra record as star.

GROSS: Why don't we hear it?


SINATRA: (Singing) Close to you, I will always stay close to you, though you're far away.

GROSS: That's Frank Sinatra, recorded in 1943. My guest is Will Friedwald, author of the book "Sinatra! The Song Is You." In his Columbia years, he primarily sang ballads, where later on in his Capital years he did wonderful ballads but he was also a real swinging singer. Why do you think he stuck so close to ballads in that first part of his career?

FRIEDWALD: Well, one of the points that Billy May makes is that this was what made him different. Everything coming out of a big band mentality with the whole swing background, and this is what people were used to hearing, was a solid four-four dance foxtrot rhythm. I mean, every record ever made was a foxtrot in four-four in those days. People really came out of this dance culture. And the way Sinatra got people to listen him, and the way Sinatra got people to say, hey, this guy's different, was by slowing it down. I mean, this is really somebody to listen to and not to dance to. He had this big, lush semi-classical sound - although I don't find anything classical in the singing, others have. But that whole lush, relaxed thing was incredibly different. I mean, even somebody like Bing Crosby, as miraculous as he was, would never have gone to that extreme, you know, with those really slow tempos. And it forced you to listen to him. And in fact, there are even accounts, statements from the day from psychologists and people like that that compare Sinatra to a mesmerist or some kind of - he had this kind of hypnotic power, they would say, in his singing, just by slowing down the tempo. And that's what gave him that romantic edge. And that's certainly what, you know, young women of that day responded to, was that nobody had ever heard any kind of a pop singer that was that intensely romantic. And that's why all the girls went ape over him at that point.

GROSS: I'm going to ask you to choose what you think is one of the best romantic ballads from his Columbia years.

FRIEDWALD: I love "I Fall In Love Too Easily."

GROSS: I love that too. OK, should we play that?


GROSS: OK, let's hear it.


SINATRA: (Singing) I fall in love too easily. I fall in love too fast. I fall in love too terribly hard for love to ever last. My heart should be well schooled 'cause I've been fooled in the past. And still, I fall in love too easily. I fall in love too fast.

GROSS: That's Sinatra singing "I Fall In Love Too Easily." And my guest Will Friedwald is the author of the book "Sinatra! The Song Is You: A Singer's Art." What do you particularly love about that recording, Will?

FRIEDWALD: Well, it's interesting. I mean, we talk about these have classical elements and that - Dave Mann, who later wrote "In The Wee Small Hours Of The Morning," plays the piano solo on that. And both that solo and the orchestration are - you know, you could say that there're some kind of classical elements to them, some kind of European romantic elements. But at the same time, it's very much in a pop vein. It never seems heavy-handed. It's very light and sweet, and there's an innocence to it. And to me, that's sort of the apex of early Sinatra in that, you know, his voice - there's a strength to it, but at the same there's such a vulnerability and a tenderness. And he sounds so open and so sincere that it really it also matches the intent behind the lyric because he talks about falling in love so easily. He's sort of being blown about on these winds of emotion and voice and the orchestration. And everything about it comes together to amplify that point. I mean, it's a really - I mean, the great thing about Sinatra records from every generation is that they all have that kind of synergy where everything sort of works together. And it's not just - you know, the song is never randomly orchestrated or sung. Everything is kind of put together with that kind of meaning. And this is a really strong early example of that.

GROSS: My guest is Will Friedwald, author of "Sinatra! The Song Is You." We'll talk more and hear more music after a break. This is FRESH AIR.


GROSS: Back with Will Friedwald, author of "Sinatra! The Song Is You."

The late '40s and early '50s were a difficult part of Sinatra's career. He was in a slump. He eventually lost his - he was dropped by his agency, his movie studio, his network and his record company in 1952 or by 1952. As you write in your Sinatra book, this difficult period is usually discussed in terms of his personal life - his tortured romance with Ava Gardner, his divorce from his children's mother - from his first wife, Nancy. But you say they were musical problems that were really getting him down here, too. What were some of those musical problems eating at him?

FRIEDWALD: I think the key issue in that point is kind of a combination of musical problems, as you say, and image problems. I mean the - as, you know, with the divorces and with that very-publicized affair with Ava Gardner, it became clear that Sinatra was not an innocent. And basically, in his music and in his film roles up until that point, he was always playing naive young things, these very kind of sweet boys, from Brooklyn, usually (laughter). I don't know why. I don't know why from Brooklyn, but from Brooklyn. But after he, you know, was pursuing this - sort of this great, hot-looking, devilish woman, Ava Gardner, then people couldn't think of him as that anymore, particularly when, you know, he had a divorce and had this big affair while he was still married. In his music, in the films and in the records, he was still coming off that way. He had that sweet sound, that innocent sound, the tender and vulnerable sound, and people weren't buying it anymore. And it was particularly against the grain of what was going on by the late '40s, where novelty records with a heavy beat were really kind of taking over. I mean, that whole era is sort of the breeding ground for rock 'n' roll because a lot of that same sensibility got, you know, transmuted into that a decade later. And Sinatra was really going against the grain of it. He was still mainly doing Gershwin and Cole Porter and people like that, and it was very antithetical to what was going on. And what Sinatra does, the way he gets out of it, is by adapting more of his own personality, or at least showing more of a tough-guy thing, you know, showing this kind of willingness to participate in these kind of sinful situations, as it were, that you don't find in the early stuff. And then people start buying him again once the music becomes in tune with that, once he starts doing the harder swinging stuff and has that kind of attitude, that kind of edge to it that he develops in the '50s. Then people believe him again. And that's really, you know, the biggest part of the comeback, I think, is - and, of course, you know, "From Here To Eternity," which is a much deeper kind of a movie role, it's more of an acting part, not just, you know, a singer who happens to be playing a character, but it's a very deep part and it shows what he could do as an actor. And, of course, the musical work from the mid-'50s onward, you know, also is very much the work of an actor by that point.

GROSS: We know that period where there are a lot of novelty hits affected Sinatra directly even though he didn't want to sing those songs. As you point out in your book, he was featured on the "Hit Parade" so whatever was no. 1 he had to sing, and he had to sing even the "Woody Woodpecker Song," (laughter), which had become a hit.

FRIEDWALD: He sang some really dreadful things there. I mean, he sang "Nature Boy," he sang "Civilization." I mean, there were air tracks of all of that stuff, and you knew - you know, you can hear Sinatra cringe, and you can hear - even on those shows where he does it, you can hear Sinatra deprecate those songs in his introductions and things like that. But, you know, those were the times, and being on the "Hit Parade," he was obliged to do that.

GROSS: And then he had Mitch Miller as his producer for some of his latter years at Columbia Records. And Mitch Miller was kind of famous for cranking out novelty songs that were also big hits that singers had to, like, sing forever after that, like "Mule Train" for Frankie Laine or "Come On-A My House" for Rosemary Clooney. What were those songs for Sinatra?

FRIEDWALD: Well, you know, to give Mitch some credit, a lot of the Sinatra and Mitch Miller things are quite beautiful. There's some wonderful ballads, like "Nevertheless" and "I'm A Fool To Want You," which is, you know, one of the great Sinatra records - of any era is from that period.

GROSS: That's a great record, yeah.

FRIEDWALD: But the way Mitch defends himself - and he has been attacked and he does need to defend himself - is that, you know, they tried doing great records of great songs, and people weren't buying them. And Sinatra was in a very low and depressed state and was willing to try anything at that point to try and have a hit. And Mitch came to him with these horrendous songs and he really did not have the fortitude, emotional or career-wise or financial, to withstand Mitch's advances. And that's why he did "Mama Will Bark," which is the most, you know, horrendous record of his whole career. It's just abysmal. And there they are, and he spent the next 40 years, 50 years after that putting those records down and putting Mitch Miller down, you know, as violently as he could.

GROSS: Well, let's take a break from all the good music that we've heard (laughter) and listen to "Mama Will Bark." Was there a dog in the studio with him for this?

FRIEDWALD: We happen to know that the guy that does the dog imitation is a gentleman by the name of Donald Bain. And I have no idea who he is, but somehow that name, Donald Bain, has been preserved. So that's the fellow who does the dog barks on this record.

GROSS: All right. Let's hear it.


SINATRA: (Singing) My feet were killing me. My dogs were barking. I must have fallen asleep where I was parking. And then I dreamed two dogs were talking. Take my word. It was the doggone-ist thing you ever heard. She said...

DAGMAR: Mama will bark.

SINATRA: (Singing) You look so lovely in the moonlight.

DAGMAR: Yes, but Papa will bark.

SINATRA: (Singing) Your eyes are shining like the starlight.

DAGMAR: Yes, but Mama will bark.

SINATRA: (Singing) Your lips are so inviting, darling. Give me one more kiss.

DONALD BAIN: (Imitating a dog barking).

DAGMAR: Mama will spank.

GROSS: That's Frank Sinatra in probably one of the worst records he ever made, would you say?

FRIEDWALD: Certainly one of them, sure. I mean, there's some awful things in the '70s. I mean, there's awful things here and there, but that's...

GROSS: Well, I guess, yeah. (Laughter).

FRIEDWALD: ...Kind of a period of concentrated awfulness.

GROSS: (Laughter).

We're listening back to my 1997 interview with Will Friedwald about his book, "Sinatra! The Song Is You." Tomorrow marks the hundredth anniversary of Sinatra's birth. After a short break, we'll talk about Sinatra's "Capitol Years" and his collaboration with Nelson Riddle. I'm Terry Gross, and this is FRESH AIR.


GROSS: This is FRESH AIR. I'm Terry Gross back with more of my interview with Will Friedwald, author of the book "Sinatra! The Song Is You: A Singer's Art." Tomorrow is the centennial of Sinatra's birth. When we left off, we were talking about his years with Columbia Records when he was known primarily as a great ballad singer.

GROSS: Why did Sinatra end up leaving Columbia and then moving to Capitol Records, where he started a whole different part of his career and a whole different sound, that swinging sound?

FRIEDWALD: Well, Columbia essentially - Sinatra and Columbia agreed not to renew the relationship when the contract ended at the end of '52. And - but within six months, he had switched to Capitol. And like Alan Livingston, who was in charge of Capitol at that time told me, he still believed that Sinatra could sing but nobody else did. And it was a real uphill battle to get the company to - to get Capitol to show any enthusiasm in the early Sinatra releases. But the whole thing was that Sinatra was able to kind of turn that high-living, skirt-chasing rat - you know, proto-rat pack image to his advantage at that point 'cause that was suddenly the in thing to be in the 1950s. Like, I mean, in the '40s during World War II, Sinatra comes on as just the opposite of sort of - you know, when our idea of masculinity is somebody like John Wayne, Sinatra comes on as very tender and very vulnerable. When our idea of the thing to be is a family man - I mean, the '50s is an era of nothing if not familial connections - Sinatra goes against that grain again by, you know, promoting himself as a swinging bachelor with a ring-a-ding-ding lifestyle. And the Capitol records, you know, particularly the up-tempo ones, promote that. And, you know, that's the image that worked for him at that point. And it happened to have a lot in common with Sinatra's real-life personality, and he used that to his advantage. And the Capitol things, particularly the swing things - and I maintain that swing and jazz were always the basis of what he did. I mean, he really comes out very - and he said it himself that he really listened a lot to Louis Armstrong and people and Ella Fitzgerald and even Sarah Vaughan, although Sarah Vaughan was, of course, much younger than he was. But he always gives credit to people like that as his main inspirations. And you can really hear that by the '50s, he was recording jazz albums very regularly, recording things with a beat, you know, all the time. And by that point, he really established himself as a jazz-oriented popular vocalist. And it's a very - those are very strong records, you know, particularly with Nelson Riddle. And, you know, the two of them really explored that whole swinging side of Sinatra and made some of the great jazz vocal records that have ever been done.

GROSS: But you say Sinatra had to be sold the idea of working with Nelson Riddle. He was very reluctant to team up with him.

FRIEDWALD: Well, we find at the very start of the Capitol period Sinatra still very unsure, very - doesn't have a lot of confidence. There's a funny story that Bob Wells told me. Bob Wells was the guy that wrote - among other things, he wrote "The Christmas Song" with Mel Torme and he also wrote the "Patty Duke Theme" later on.

GROSS: (Laughter) They're identical cousins.

FRIEDWALD: Exactly. He invented the concept of identical cousins. But he also wrote the lyrics to "From Here To Eternity," which is, you know, one of the early Capitol singles and, you know, a big part, of course, of the Sinatra comeback. And he said that at the session from "From Here To Eternity," Sinatra was very sheepish, very reluctant, very nervous. And he kept saying, was that all right, Bob? Did I do that OK? Did you like it? And he would - you know, he really needed acceptance and he really needed people to pat him on the back and say, yeah, Frank, that was great. And then Bob said that about six months later, after he won the Academy Award and after he was back on top again, he saw Sinatra at some kind of event and Sinatra said something like, how you doing, kid? You know, it was like Sinatra was...

GROSS: (Laughter).

FRIEDWALD: ...You know, he was on top and he was, you know, not talking down to him, exactly, but, you know, you could tell that he was dealing from a position of strength at that point. And it was just like their relationship had totally gone 180 degree angle. Sinatra was now - you know, he was totally just rejuvenated and reanimated and, you know, he had - you know, he had experienced the comeback by that point and he was the new Sinatra.

GROSS: Nelson Riddle has said - you report in the book - that he always let Sinatra choose the tempo. And I think Sinatra really had a gift for redefining what the tempo for a song should be and, you know, reworking, rethinking a song giving it a new sound.

FRIEDWALD: Well, the - one of the amazing things about Sinatra overall, I mean, going back to the Columbia period and in the work with Riddle in particularly is that Sinatra always had total control of what was going on musically. I mean, this is an era when we think of, you know, somebody like Dinah Shore and Nat Cole or even Bing Crosby. Basically, you know, they would just show up at the session and be told what they were going to sing and how they were going to sing it. With Sinatra, it's just the opposite. He would plan all his sessions himself, and he would go to the dates and tell his producers what he was going to sing and how he was going to sing it. I mean, he was the one dictating all that. And this comes to the fore really acutely in the work with Riddle because Riddle was a very dynamically talented young arranger when Sinatra first met him. But he was someone who did not have an individual style of his own at that point. And working with Sinatra really helped Riddle develop what became the Nelson Riddle sound - the Nelson Riddle style, which is, you know, automatically identifiable whenever you listen to one of his orchestrations. And in a sense, I think that Sinatra saw Riddle, at that point, as a blank page on which he could write. And he and Riddle very carefully planned those records. Sinatra would not only dictate tempo but as Riddle has said, he would say that, you know, when the song starts for the first 8 bars, I want strings behind me. Then for the next eight bars, I want to have a trumpet obbligato and then I'd like to have, you know, whatever - you know, some kind of flutes or something like that or trombones. And he would really sketch out those records from, say, you know, eight bars to eight bars or four bars or whatever - you know, down to the tempo, down to the texture - you know, all that kind of stuff. And of course then he had also said that after, say, if he planned, say, 14 songs in a 16 songs album, he might get tired and let Riddle do what he wanted for the other two or something like. But basically those records are really keen and very exacting collaborations between Sinatra and Riddle. And Sinatra's input goes way beyond, you know, the singing itself. I mean, he had a lot to do with the sound and the feel of those orchestrations.

GROSS: Let's play one of the great collaborations between Nelson Riddle and Frank Sinatra. And I know this is a favorite of yours, "I've Got You Under My Skin."

FRIEDWALD: Oh, that's a favorite of everybody's.

GROSS: Yeah (laughter), and this is a Cole Porter song, and I don't think anybody quite swung it like this before Sinatra.

FRIEDWALD: I certainly don't know of anyone, although now it's impossible to think of it any other way than as a swinging number like this.

GROSS: Tell me why else you love this recording.

FRIEDWALD: Well, to me, this is the perfect example of the way Sinatra uses music and drama and puts them together but in a way that's not at all heavy or didactic or anything like that. I love the parts of it where Sinatra is, you know, really singing a love song, where his, you know - his whole purpose is to express the fact that he's in love with somebody and, you know, perhaps trying to woo somebody. And he's very sincere at certain points. And at other times, he's just totally playing with - I mean, at other times, he acts like the lyrics don't matter to him at all, that they're just baubles for him to play with and he just throws them away, he just tosses with them. He bounces them like a toy balloon. And he does all these things. And his whole attitude changes and adapts from, you know, line to line, even - from four bars to four bars. He just really - every line is - I mean, of course for Sinatra, every song he gets precisely the right character, precisely the right attitude. And I think this is really what, you know, pop singers have learned from him since then. But it's so wild to see him doing that just from, you know, word to word almost in that song the way he changes. You know, sometimes he's totally sincere and sometimes he's totally irreverent and flippant. It's just a miraculous piece of pop singing.

GROSS: So "I've Got You Under My Skin," and this is - what? - the mid-1950s?

FRIEDWALD: This is 1956, I believe.

GROSS: OK, here we go.


SINATRA: (Singing) I've got you under my skin. I've got you deep in the heart of me. So deep in my heart that you're really a part of me. I've got you under my skin. I tried so not to give in. I said to myself this affair never will go so well. But why should I try to resist when, baby, I know so well I've got you under my skin? I'd sacrifice anything, come what might, for the sake of having you near in spite of a warning voice that comes in the night and repeats, repeats in my ear, don't you know, little fool, you never can win? Use your mentality. Wake up to reality. But each time that I do, just the thought of you makes me stop before I begin 'cause I've got you under my skin.

GROSS: My guest is Will Friedwald, author of "Sinatra! The Song Is You." We'll talk more and hear more music after a break. This is FRESH AIR.


GROSS: Back with Will Friedewald, author of "Sinatra! The Song Is You." After Sinatra left Capitol Records, he formed his own record company, Reprise, with Mo Ostin. Why did Sinatra want his own company?

FRIEDWALD: I think that from the beginning, Sinatra always wanted to totally control and own everything he did. I mean, even as far back as the Dorsey period, he's virtually the only band singer that has any kind of the influence in picking his own songs. And throughout the Columbia period, Sinatra is really in charge of everything on every level, from the songs sung to the way they're arranged, and even the technology. I mean, there are certain session recordings and studio tapes where we can hear Sinatra as far back as, like, 1949, actually directing things like the placement of the microphones and telling the trumpets where they should stand and the trombones which direction they should face. Sinatra always had control. And eventually, he would get to the point where he wanted ownership. And this is against the background of a period when - particularly in the 1950s - when the big institutions, the big studios, the MGMs and the Paramounts, were, you know, beginning to relinquish control to independent producers. And also, in the early years of television we have this whole breed of performer moguls - people like Sheldon Leonard and Danny Thomas and Desi Arnaz and Lucille Ball, of course, were the number ones. But there was - you know, this tradition was being to develop of performers that controlled their own material. And Sinatra was really the first major star to try that as far as the record industry went. And he went to Capital, to which he had just signed a new contract, which made it difficult, and said, I want this arrangement where I produce the stuff and you distribute it for me. And they wouldn't go for it. So from that point on, he became resolved to start his own company. And at one point he tried to buy Verve Records, and that's where he met Mo Ostin, who was the controller for Verve. And although he didn't wind up with the company, he and Ostin, of course, got together and formed Reprise and, you know, were together for many years with that company. And that was really the first major example of a recording star who controlled his own masters and owned his own company. Interestingly, it sort of had happened in jazz to a much smaller degree. Charlie Mingus owned Debut Records and Al Hall owned Wax Records and Louis Prima owned Robin Hood Records for a while, but none of them were really, you know, major corporations that floated stock options and things like that. I mean, this was a very unique thing for a recording artist to do. Essentially, the notion of Reprise as a completely autonomous entity only lasted about five years when he was bought out by Warner Bros. for, you know, an outrageous sum. I mean, it was this deal that included his motion picture contract, and they're taking over the company. And, you know, it's for millions and millions of dollars. It was, you know, an unheard-of-ly (ph) astronomical amount at the time.

GROSS: Did Reprise give him the kind of artistic freedom and independence that he wanted?

FRIEDWALD: Well, Reprise was - whatever he wanted to do, he could do it. And you see it in things like his tribute album to Tommy Dorsey, which is obviously a very personal project. And I'm sure Capital would have done it. But to me, it's typical of the kind of thing that he really wanted to do on his own. And the Count Basie collaborations where, you know, previously you couldn't really do that because, you know, Basie was under contract to another label and that was a lot - that was a difficult thing to manage. But being in charge of the company and, you know, having the kind of freedom, Sinatra made sure to do it. And that was a major Reprise project - the same with collaboration with Jobim and with Ellington. And the whole Reprise thing where he's working with lots of different people at once - that really became the standard for his work at the company. And I think that's because he didn't want what had happened to him earlier, which is when people got tired of the '40s sound, he had a very big sort of gap before he was able to develop the '50s sound. So even before people got tired of the Sinatra-Nelson Riddle '50s sound, that's when he starts experimenting with lots of different arranges and lots of different textures and lots of different sounds because he doesn't want people to get tired of any one thing that he's doing. And so in a year like 1962 or 1963, sometimes he's working on, like, 10 albums at once with 10 different arrangers, and they all sound completely different.

GROSS: Why don't you choose one of your favorites from the Reprise era?

FRIEDWALD: Well, you couldn't go wrong with, like, "Pennies From Heaven" from the Basie album. That's really a classic piece of Sinatra swing.

GROSS: Let's hear it.


SINATRA: (Singing) Every time it rains, it rains pennies from heaven. Don't you know each cloud contains pennies from heaven. You'll find your fortune's fallen all over the town. Be sure that your umbrella is upside down. Trade them for a package of sunshine and flowers. If you want the things you love, you must have showers. So when you hear it thunder, don't run under a tree. There will be pennies from heaven for you and me.

GROSS: My guest is Will Friedwald, author of "Sinatra! The Song Is You." Your book on Sinatra is really like a listening companion. It's about Sinatra the singer. It's about his voice, his recording sessions, his approach to music. It's not about his love affairs; it's not about his early childhood. You really keep all of that in the background or out of the book completely. And I'm wondering why you wanted to do that - why you wanted to focus so specifically on the voice and the approach to music.

FRIEDWALD: Well, it just occurred to me that since he is the number - I mean, I don't even think it's worth debating. He's certainly the number one performer in the whole - the genre of American pop, particularly the American popular song. He's certainly the single most important figure - be it songwriter or arranger or singer or whatever. I mean, he's really the person that defines this whole idiom. And it's, you know, an amazingly vast and oceanic idiom - capacious. And, you know, the mere fact that Sinatra is the single most important figure in this field and that no one had ever done a book which studies that at any kind of length at all - you know, I think, like, there's one reference to Nelson Riddle in all of Kitty Kelley. I mean, if you look in the index under "Riddle, Nelson" it says, page 275 and there he is. But, I mean, the fact that no one had ever done that always struck me as a major loss.

GROSS: That probably means they never slept together.

FRIEDWALD: Yeah exactly, exactly.

GROSS: Will Friedwald, a pleasure to talk with you. Thank you very much for talking with us about Sinatra and your book "Sinatra! The Song Is You."

FRIEDWALD: Thank you.


SINATRA: (Singing) Come fly with me, let's fly, let's fly away. If you can use some exotic booze there's a bar in far Bombay. Come on and fly with me. Let's fly, let's fly away. Come fly with me. Let's float down to Peru. In llama lamp there's a one-man band and he'll toot his flute for you. Come on, fly with me. Let's take off in the blue. Once I get you up there where the air is rarified, we'll just glide, starry-eyed. Once I get you up there, I'll be holding you so near. You may hear all the angels cheer because we're together. Weather-wise, it's such a lovely day. Just say the words and we'll beat the birds down Acapulco Bay. It is a perfect for a flying honeymoon, they say. Come fly with me. Let's fly, let's fly away.

GROSS: Will Friedwald is the author of "Sinatra! The Song Is You: A Singer's Art." Our interview was recorded the year was published in paperback, 1997. Tomorrow marks the hundredth anniversary of Sinatra's birth. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.