Frank Sinatra: Through The Lens Of Jazz

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Frank Sinatra
By William Claxton
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Frank Sinatra
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Frank Sinatra
By William Claxton
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Frank Sinatra
By William Claxton

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Frank Sinatra turned 83 last December and as the 20th Century draws to a close, we offer this tribute to a man whose impact on our popular culture has been preeminent.

Later this year, Hofstra University will play host to a Frank Sinatra Conference for in-depth scholarly discussions on all aspects of his life and impact including his recordings, the dynamics of courtship and love in his songs, his film and television career, his multigenerational influence, his politics and involvement with the civil rights movement, his part in the subculture of Las Vegas casinos, his philanthropy, his effect on society and even his work as a painter.

Our homage to the Chairman of the Board a.k.a. Ol’ Blue Eyes a.k.a. The Voice will focus on his music although any Sinatra story is really about much, much more.

Frank Sinatra went from teen idol to living legend, and, without formal training, developed a highly sophisticated style. His ability to produce long, flowing musical lines unbroken by pauses for breathing, his subtle use of the vocal techniques more commonly found in the opera and classical idioms, and his manipulation of phrasing, reminiscent of Billie Holiday, set him far above the average pop singer.

Like Elvis Presley, the next singer to experience mass adulation, Frank Sinatra developed a unique white-blues style, supple enough to express the wide range of his own turbulent emotions. He transformed the songs of the great writers into something personal by the sincerity of his performance; Sinatra actually seemed to believe the words he was singing.

He has faced triumph, failure and triumph again throughout his long career as an entertainer. New musical fads and trends have come and gone during his lifetime but this man and his music have remained at the forefront of American culture for nearly half a century.

Listening to his recorded legacy, an incredible body of work that spans 1939 to 1994, there can be little doubt that Sinatra is the single greatest interpreter of American popular song—the one performer who elevated what he referred to as “saloon singing” to a high art. A man who has enriched American music with countless superior recordings of many classic standards and provided the soundtrack for much of this century.

Sinatra has touched many lives and for this tribute, we spoke with a cross section of people from the world of jazz.

John Zorn: There are so many things about him. His musicality, his timing, his creativity.

Fred Hersch: Great phrasing, great breath control.

Joe Lovano: His personality, his feeling, his tone. Frank Sinatra emerged in the late ’30 and ’40s, alongside Billie Holiday and Lester Young and Coleman Hawkins and Ben Webster...Sinatra’s sound, his voice, had the same meaning and impact as the great improvisers and players of the tenor saxophone. He’s one of the few cats who spanned all these different generations and always projected amazing glow, like Miles Davis did, in a very similar way.

Tommy LiPuma: Miles told me that on Porgy and Bess, he wanted his trumpet to sound like Sinatra.

John Zorn: There are inside records, which are outtakes, from both the Capitol and Reprise years and on them, you hear take after take of Frank Sinatra and in a sense, he’s just as creative an improviser as Charlie Parker. Every take is different, he approaches each in a slightly different way. He’s always searching.

Sinatra’s a total musician in the sense that he’s not just a singer; he’s a passionate, dedicated, effective searcher who wants to be in control of all the action. He’s a perfectionist, as you can hear on some of the bootleg records from the studio. He knows how to set the mood, he knows exactly what’s happening in the orchestra. He’ll say, hey, that trombone player, that note is getting in the way of my range. I’m a little weak, he explains in a session, this note is a little weak, can you change the voicing of this chord. He knows exactly what’s going on and he gets what he wants.

Jimmy Amadie: In addition to his sound and presence, Sinatra has the ability to sing a tune in any style and make it sound like his own. The sound is always rich and full and no one interprets a tune that is more believable than the way he has with both the music and the lyrics. An example of this magnified is when you hear the music of the various arrangers in the background and the way in which Sinatra blends, it is chameleon-like. As a musician, you can feel what he is doing and at that moment you want to be a part of it.

Whitney Balliett: Sinatra loved Mabel Mercer. He idolized her and at the same time, starting back in the ’60s, for some reason, he seemed to fall under the influence of Billie Holiday. At the time, his whole rhythmic attack changed very much like Holiday. Of course Billie loved Mabel Mercer too, but they were total opposites as singers. Mabel had fantastic articulation, the way she handled a lyric was extraordinary in terms of singing. It seemed to me that’s when he started doing that kind of highly rhythmic singing, in the early ’60s.

Ken Peplowski: Frank Sinatra transcends titles but you could call him a jazz singer. I don’t think jazz singing is defined by scat singing or improvising. His form of improvising is making a song his own and interpreting it through his own experience. He shaped every song. There are certain tunes you listen to now, you think this is a Frank Sinatra song. He constantly evolved his interpretations over the years, just like all the great jazz musicians. You could go to hear him five nights in a row and the songs wouldn’t quite be the same every night. If that’s not jazz, I don’t know what is.

Monty Alexander: Every time I hear people get into these little arguments about whether or not he was a jazz musician, I got to laugh because he’s bigger than that. To me a jazz singer is just someone who’s interpreting great songs with a groove on it, and that’s what he did. I saw him as this man who was up there swinging away. And then of course, the way he’d sing these tearjerking ballads, man, it’d make you cry. If you had a crush on some lady and you heard that music in the background, it’d take you to another level.

Joe Lovano: With his ballad stylings, he really told a story when he sang a tune. When you listen to different records, you can hear the same tune done sometimes with a similar orchestration but his interpretation would always be really free. I think that’s what Miles and a lot of cats dug about him. You could hear a lot of that in the tunes that Lester Young was recording at the same time. There’s a lot of similarities in the presence, the purity, the way they deliver a tune, with so much meaning.

Jane Ira Bloom: When I play a ballad like “In the Wee Small Hours Of the Morning,” I think about the way he would extend his breath lengths past the usual phrase lengths in the tune. It gave the melody an arc that always pushed your emotions forward.

Sinatra was the key to an instrumental piece I wrote (“More Than Sinatra” on Modern Drama) about a relaxed melody that arches up and down across the bar line with a distinctly vocal feel. It was Sinatra’s sense of phrasing that spoke to me. Not just how you start the phrase, but how you finish it.

Joe Williams: Frank’s personal interpretation of a lyric, it’s like people who read poetry, or an actor in a role, with Frank each song is a vignette for the story, and he tells it like nobody else.

John Zorn: Like all great artists, Sinatra has his periods. Each is different. For me the favorite is really the Reprise years, because he was so confident with what he was doing. Of course the Capitol years are incredible as are the Columbia years. They’re all special times. But Sinatra is someone who developed and who lived and who learned and changed, and it came out in the music. It’s no great revelation to say that his voice matured and got deeper and got more confident, but that’s what I hear. There’s a worldliness, it gets deeper and deeper as the years go on. In The Wee Small Hours, there’s a lot of living in that record. Sinatra is someone who just continues to grow, to learn, continues to search and that quality comes through, throughout the body of his work.

Marian McPartland: All the other stuff in his life, maybe if he hadn’t been like that, he wouldn’t have been such a great singer. It all melts in together, his experiences. I can’t imagine a guy singing like that who’s going to be a quiet, well-behaved, normal guy. In many ways he was normal. Of course, a lot of other people chase women today, even Presidents, but Sinatra did make an art form of it, then he took all that stuff and put it into song.

James Moody: I did an album of Sinatra tunes because I like all the songs that he chose. They were profound tunes, tunes with substance. They’re standards but they were beautiful standards with a lot of meaning to them, really good compositions.

Sonny Rollins: On my first album, I recorded one of his songs, “This Love of Mine.”

When I went to high school, I lived in Harlem, but they built a new school on 116th Street and Pleasant Avenue, which was right in the middle of an Italian area. They needed more kids to fill up the school so they bused some of the kids from my neighborhood down to the school. Now coming into this Italian neighborhood, as black kids, we were resented. People in the neighborhood used to throw stuff out the windows at us and swear. It was like walking through Beirut, and then of course in the school, there was a lot of bad feelings.

The problem was so bad over there that they had two famous artists come to the school, to perform and try and talk to the kids. One of them was Nat King Cole and the other was Frank Sinatra. Nat Cole played, I don’t think he talked too much, but Sinatra sang and lectured the kids about not fighting and being brotherly. Things actually got better after that.

Marvin Stamm: When Sinatra came out of retirement in ’73, I was playing lead trumpet in the orchestra that toured with him...there were nights when he could make the hair stand up on the back of your neck. And those charts, they were just wonderful. You never got tired of playing them.

Patrick Williams: I worked with Frank on the two Duets projects, and I’ve just released an album called Sinatraland, with arrangements of his tunes inspired by the original arrangements and dedicated to his arrangers.

When we did Duets, I was doing the arranging and what I did was to get a number of scores, about 50 or 60, from his library, trying to figure out what might adapt well for duet possibilities, and how best to treat them. I was absolutely shocked when the scores came to the house.

To look at that music and realize what all that was about just really knocked me out. Those arrangements were written at such a high level. Everybody who worked with him along the way went a notch higher, in terms of the level of artistry, mastery, musicianship, personality and even humor. Anything you can think about was right there in those pages. Sinatra’s charts are the sum total of the arranging experience.

Nelson Riddle was the best vocal arranger who ever lived. What he did with Sinatra, I’ve never heard anybody come close to. Not to denigrate anybody else but there was something about the way that Nelson fit with Sinatra’s musical sensibilities that was an exquisite pairing.

Billy May was also right up there. For me it was Nelson Riddle and Billy May and what happened with the magic there was incredible. Of course the other arrangers were all heroes of mine as well. Right down the line, there wasn’t a chump anywhere, Neal Hefti and Quincy and Billy Byers and Johnny Mandel, all these guys are just incredible talents. Frank had the best, no question about that.

Bucky Pizzarelli: They don’t make them like Frank anymore because they can’t. Look at where he came up. In the big band era. Frank was traveling around in buses like everybody else. Singing all the songs like anybody else, but he also happened to be the best.

In those days, you had nothing to worry about. No rent; you had a hotel, and that’s all you had to do was travel around and play. You’d meet chicks, do whatever you want, and just get your craft going. Each night you tried to do better than the night before, that’s how you work it out. Frank, he had his own set of rules, of how he presented himself, he didn’t want to deviate from that one way.

Joe Williams: I first heard him about 1939 or ’40 singing with Harry James and his orchestra broadcasting from Chicago. I recognized him right away as a very distinctive and positive sound that I wanted to hear.

I was in a car and made everybody be quiet so we could hear it. Then when he finished I said, ‘a-hah.’ I can even tell you the song he was singing, “It’s Funny To Everyone But Me.” Other than the Ink Spots, the only other person that was singing it was me, on the radio with Jimmy Noone’s orchestra out of Chicago, on WBBN, so I could relate to hearing it.

The next thing I remember was when he did “All Or Nothing At All.” He’d taken the place of another singer I’d been listening to, Jack Leonard, who was with Tommy Dorsey’s Orchestra. Jack went into the army, Frank joined Dorsey and, from then on, he just took off because he had an audience and the perfect setting with the Tommy Dorsey Orchestra and the Pied Pipers.

Ken Peplowski: It was always fascinating to hear how he changed as he got older. Obviously his instrument didn’t give him as much as it did when he was younger but he worked around it and found ways to be even greater in his last few years than earlier. He got more into the pure emotion of the song, the pure feeling, which a lot of instrumental musicians also do. Benny Goodman did that as well.

Frank reduced everything to a very simplistic palette, he reduced everything to pure swing, to pure feeling. There’s a parallel in all art forms; Picasso, for example. As these great artists got older, they got simpler. They paired everything.

Frank Sinatra is as responsible for me playing music as Benny Goodman or Sonny Stitt or any of my instrumental influences. My goal as a musician is, if I play a standard, if I can convey the same feeling that he has, then I’ve succeeded 100%. I’ve never heard anybody in life who gets into the emotion of a song as much as him, and also swings as hard.

I was working in Benny Goodman’s last band and we were working a big fund raiser at Radio City Music Hall. It was Benny, Placido Domingo, Ella and Sinatra and I remember thinking that night, that each one of these four people is head and shoulders above anybody else in their respective categories as musicians and once they go, that’s the end of that type of quality and greatness.

Joe Williams: I was working at the Flamingo in Las Vegas, with Basie—this was in the early ’60s. There was an album cover of Frank with his hat cocked to one side, his coat thrown over his shoulder. Well, that night, I had my big coat with me and as I left the stage, I mimicked that. After the last number of my set, I threw my coat over my shoulder, cocked my hat and went off the stage. The audience went wild.

Al Grey: Sinatra just loved the Count Basie band because there wasn’t any other band that could play his charts like the Basie band could. And that was a tremendous help in making him a jazz singer. A jazz singer.

We played in England together, in Florida, Washington, D.C., Detroit, Chicago, everywhere, he just loved that band. He demanded that band. He would use Buddy Rich or Woody Herman or some other big band sometimes, but these bands couldn’t phrase like the Basie band. The musicians in the Basie band, they paid attention to the singer out there and forgot themselves as players. It was just, play your part to make him sound good.

The reception was, well, we would go into Las Vegas and we’d play and after the show, we’d have to hang around for an hour just to sign autographs. It was a must, you couldn’t just leave.

Sinatra, after the show, he would relax and come on out. He’d see you over there at the tables and if you’d lost all your money, he’d come over and reach in his pocket and say, here’s a hundred, why don’t you get on home now, and all like that. He was really wonderful that way.

Something that people don’t know is that Frank Sinatra paved the way for a lot of the work that jazz musicians could get out there. When I first joined Basie, booking agencies didn’t like to advertise the musicians who played with the Basie band. The billing read, ‘Count Basie, the most explosive force in jazz.’

It started with the Benny Goodman band when all the stars in the band went out on their own, like Lionel Hampton and Teddy Wilson and Harry James. So Willard Alexander, who was booking the Basie band, decided not to publicize Al Grey or Lockjaw Davis, they were just part of the band. In case they’re not there tomorrow, the band could still be sold at the same price.

Then Sinatra came along and said, I want to see some of those guys’ names up on the marquee. This is when they put five of us up on the marquee, Freddie Green, Sonny Payne, Marshall Royal, Lockjaw Davis and Al Grey. That meant I could go to Basie and say, look, this is the time for a raise.

One time we were appearing with Sinatra in Chicago and a review came out and the writer wrote about Sinatra and me, and there was a picture of me in the paper where the picture of Sinatra was supposed to be. I really didn’t know anything about it.

Well, we were coming out of the hotel the next morning to start traveling and Basie just said to me, Yeah, I saw it, and you’re not going to get a raise.” I said, “What you talkin’ about, Chief?” He said, “Oh you haven’t seen it yet?” and I hadn’t. Then I did see it and I said, wow. But I still didn’t get a raise.

Mike Smith: My parents were big Sinatra fans so I grew up listening to Sinatra but I never thought I’d have anything to do with him. I got involved with him through Buddy Rich. I was playing an alto in Buddy’s band and in 1981, we started doing tours with Sinatra. We played the Concert For The Americas, a couple of weeks at Carnegie Hall, a lot of gigs with him, and that went on for a couple of years. At the time I met Joe Mallon, who was the music contractor for Frank for 30 years, and through him, I got to do some of the gigs after I left Buddy Rich’s band. Six years later, I started working for Frank, Jr., then when Frank, Jr. became the conductor for his father, I got on board as a full-time staff member...

When we started doing the gigs with Buddy, most of us in the band were really young and here’s this big icon who’s larger than life. It was very intimidating.

I remember the first rehearsal we did. He ran the rehearsal. He would stand in front of each guy as we were playing. He’d say, “OK, I want you louder, you play softer.” He knew exactly what he wanted which was pretty amazing because most acts don’t do that. He was very involved with the music. He really knew those arrangements, the charts by Nelson Riddle, Billy May and Don Costa after all those years. He knew exactly what they were supposed to sound like and what he wanted from them. It was intimidating.

Frank was demanding but not difficult. He loved musicians. He treated you with nothing but respect. If you didn’t produce, you weren’t there. That was basically the way it worked. If you didn’t give him what he wanted, you weren’t there. But if you were part of the team, you couldn’t ask to be treated better as a musician.

The wages were incredible and the accommodations were nothing but five star, we only flew first class. Frank was a very generous guy. We had dinner together sometimes and he’d tell stories. Frank is a great storyteller, especially about the old big band era, like his Tommy Dorsey stories. I think he really enjoyed hanging out with the musicians and doing that...I remember we hung out with him in Monte Carlo. He was very overpowering in his presence; he really had a charisma that I’ve never seen anybody have and that also came across on the stage when he performed.

From night to night, he did the tunes differently. You really had to be on your toes because he was changing lyrics...if we were in a certain town, he’d slip a word in there that related to that town. He’d change up his phrasing, sometimes he’d go ahead, sometimes, he’d pull way back. He’d want tempos to be different.

It was a great learning experience as an instrumentalist to listen to him, especially on the ballads. He had a tendency to pull way back on the time, and then just before you think, oh oh, it’s going to fold, he’d be right on it. That push-pull thing. Miles was like that too. He was influenced heavily by Frank’s ballad singing.

Monty Alexander: In the ’60s, I played at Jilly’s, a club in New York owned by Frank’s friend, Jilly Rizzo. Miles used to come in there because Miles liked to go where the hip stuff was happening. He would come in there with a couple of people and sit at the bar.

I remember one time when Miles came into Jilly’s and hung out with Frank. That’s right, Miles and Sinatra! It was kind of curious to see these two men at two or three in the morning having a few drinks, sitting at the piano bar right next to me engaged in some deep conversation.

I remember the mood in that place, late at night. Sonny Payne and Lockjaw Davis might come into the joint and they’d be sitting at the bar hanging out with Frank. There was a remarkable familiarity that Sinatra had with those kinds of musicians that made me see him as a jazz person.

No, Jilly’s wasn’t just a watering hole for a bunch of idiots. A lot of jazz people came in there. You could easily find Erroll Garner sitting there playing the piano. Jilly’s was quite a place; that’s why I recorded, “Echoes of Jilly’s.” It wasn’t just about Sinatra, it was a tribute to Jilly Rizzo and Frank Sinatra. They were responsible for bringing me to New York.

I was about 19 when I started working at Jilly’s and the whole thing in this little club, the reason why it was successful was because of Frank Sinatra. Back in the ’60s, the hip crowd, the late night crowd, everybody from show biz, entertainers, musicians, the socialites, the TV people, they all knew that’s where Sinatra hung out. He was like the king of show business and he would come in the club whenever he was in town. There was always this buzz of excitement because Frank might come in at any moment.

I played there on many occasions when he would be there ’till five in the morning, just hanging out with his friends. We’d provide the music for the 20 people who were hanging out in the back talking with Frank while he had his Jack Daniels.

I wasn’t in the inner circle or anything like that but sometimes he would say, “Hey kid, I want you to come over to the apartment and just play some music.” I remember once Sam Butera, who used to play with Louis Prima, and I went over there and played late, just hanging out and playing songs.

Oscar Peterson: Having toured but never having recorded with Frank, I can still envision him dedicatedly standing in the wings each night as my trio performed the first half of the concerts.

I also recall an appearance of the Trio at the Century Plaza Hotel in Los Angeles. Frank came down to hear us but due to an onslaught of fans in the room, had to make an early exit. I received a call the next night from one of his staff informing me that Frank would like to have an after-hours party for me at his home in Beverly Hills. He sent cars for the Trio after the gig at the Century and when we arrived at his home, I was greeted by a host of Hollywood luminaries. I had earlier agreed on the phone to the Trio playing for Frank in the comforts of his own abode, so consequently after greeting and socializing with the guests that I knew, we proceeded to play a couple of numbers for him. During our performance, Frank stood behind the bar with his face cupped in his hands as he listened intently. I invited him to sing one with us but he declined, saying tonight was his night for listening. At some point, he gave me the indication that we should not give the guests any more of a performance, after which we spent the balance of the night partying ’til the early hours.

I don’t believe I have ever seen a more low-key or congenial Frank, and this is the way I prefer to remember him even to this day.

Al Grey: Frank loved to play Las Vegas in the ’60s. He owned that town. I remember when I was with Basie and we recorded Sinatra Live at the Sands. It was during the last week in January, in 1966. We had rehearsed to go into the Sands almost a month before he came to town, just to rundown the charts, with Quincy Jones. Quincy took over everything.

Arnold J. Smith: This is Sinatra at his coolest…especially where he says, “I feel sorry for those of you who don’t drink because when you wake up in the morning, that’s the best you’re going to feel all day.”

Phil Ramone: I was at that gig. I went out to the Sands and it was probably the biggest moment in my life, ever. I went out to Las Vegas with twelve cents in my pocket and a fake black jacket with a fake tie that looked like a tux. Quincy was conducting the Basie band and he had my only tux, the only one I owned. Sinatra Live at the Sands is one of my favorite recordings because everything in it not only reflects the sassiness of Frank—there’s that thing that Frank does that a lot of people mistake for cockiness and stuff, but it’s not that. It’s the way he approaches the songs that makes you feel so much.

Patrick Williams: The gig at the Sands was the first time that I’d ever seen Sinatra in person. I was arranging an album with Steve Lawrence and Edie Gorme, and they opened the night after he closed so I was out there working on some things with them and got out there when he was in his last two or three days of the show. It was just incredible. I’ve never seen anything quite like it.

It wasn’t just about him being the great singer he is, he’s a great showman and entertainer, he had this presence about him. People were going bananas, and the band was just swinging its ass off. There was an electricity to the performance that I was totally unprepared for. I was about 25, a few years out of college in New York, doing arranging. It was early in my career. Of course, I’d heard all his records, I was a big Sinatra buff, but when I saw him in person at the Sands, when that record was made, it just totally turned me around.

Phil Ramone; Frank Sinatra represents a style that is that utmost of professionalism. It’s a standard that I’ve tried to live up to since I started engineering and then producing. It’s the same standard that we could all learn a great deal from because it puts everything up front early. It makes for a much more solid performance out of all the musicians, rather than that wait- I’ll-fix-that-later kind of attitude which a lot of us have developed because of the convenience of multi-tracks.

When you’re in the studio with Frank, it’s amazing when you realize how the level of performance comes up to his level. The musicians play with such a great attitude. It’s music of the moment and they come to life. That’s something that Sinatra brings to the studio and something I’ll never forget.

His attitude is the greatest thing to learn from—that and the immediacy. That’s why he is famous for his take one or take two. Sinatra has prepared himself and he’s very tough on himself if something goes wrong. That’s why a lot of the false stories about him have surfaced. He’s not a nightmare and neither is Streisand and neither are a lot of the great artists, the Paul Simons of the world. They’re really diligent professionals who want to make that moment count. It doesn’t count 30 times later or 40 takes later, it just doesn’t work the same.

It’s a great lesson to always remember that when you go in the studio—people peak at a certain point and sometimes quite early because of the enthusiasm and the love you have for the music...first takes or second takes are brilliant. They may have a couple of clams in them, but they’re brilliant and with aid of an electronic blade or good producer, you can cut together some of the greatest things ever done. Over the years, I’ve worked with some of the greatest jazz musicians in the world and I’ll never forget how some of their best albums were done, in one or two takes. Like Sinatra.

George Avakian: I was at Columbia in the early ’50s and did some A&R work with Sinatra on two sessions. At that time, I was more or less an apprentice finding out how things were done in the studio with a large orchestra providing accompaniment. Sinatra was very easy to record. He knew what he wanted and he was ready at all times. We got through in maybe three takes, which is not the ordinary thing with most singers.

Patrick Williams: When we did the Duets recordings, Frank was 78 so it was not a slam dunk. They’d been trying to get him back in the studio for years. Sinatra took his recordings very seriously, he was extremely proud of what he’d done in the studio, over many years. When he decided to do Duets, he came in and gave it everything he had. The courage, the outright courage that this guy has just knocked me out. He was focused, he was ready to go. I just tried to stay with him. I had all the arrangements rehearsed before he came in, so we weren’t going to rehearse anything, we were just going to start recording and see how he did. He’s fast, he knows what he’s about, he’s completely on top of it. Everybody in the band just felt this tremendous electricity when he started to sing. He may not have had the voice he did 25 or 30 years ago, but he had so much going, in terms of sheer ability, that everybody was just loving every minute of it.

Phil Ramone: He’s a guy who, historically, is in everybody’s life. You can chronologically figure out where the hell you were and what you were doing by the Sinatra of your time.

Marian McPartland: There must be millions of women all over the world relating to romantic episodes that Frank had a part in, even though he didn’t know it.

Jimmy Amadie: Sinatra as a singer is what Caruso was to opera, and Joe Louis was to boxing—one of a kind.

Sonny Rollins: He’s also a guy like Louis Armstrong was, he took care of his friends. But he didn’t do it to get notice in the paper...

James Moody: It’s only hearsay, but I’ve heard that when Joe Louis had his surgery, Frank Sinatra paid for it and kept him going until he passed. Sinatra helped a number of people in that way. That kind of makes you kind of dig a person a little bit too.

Joe Williams: Many, many times I’ve seen how music has healed people. It’s a very spiritual thing and it comes through him, through Frank Sinatra. Through his performances to an audience that has the antenna to receive it, and bathe in it.

I wrote once, those who seek the harmony of life rather than the discord, truly inherit a kingdom of love. In music, people come to hear you because they want you to strike that harmonious, spiritual chord in them. Frank Sinatra always struck that chord.

The A-List

While this tribute was assembled, five Sinatra recordings were mentioned repeatedly. For some expert opinion, we spoke with three self-confessed Sinatra-philes: Jonathan Schwartz has been playing Sinatra’s music on the radio in New York since 1967. Arnold Jay Smith is a walking Sinatra encyclopedia. Will Friedwald wrote perhaps the best books on Sinatra’s music, Sinatra! The Song Is You: A Singer’s Art.

1) Only the Lonely

Schwartz: It’s Sinatra’s favorite and he’s told me that many times, personally...also it contains, Nelson Riddle told me, his favorite arrangement, “Willow Weep For Me.”

Smith: Grammy winning cover. Easily his best reading of “One For My Baby,” which became the trademark version because of the piano introduction, and he used this for his saloon singing medley in performance. Even though these songs were around for years, once he recorded them, his versions became the standard.

Friedwald: The most classically oriented Sinatra recording, particularly the title track, which opens with a Chopin-like piano solo played by Harry Sucoff, a classical pianist. But although this was as close as Sinatra got to singing in a classical style, it still comes from a jazz foundation rhythmically...“One For My Baby,” the definitive saloon song, has his regular pianist, Bill Miller, on piano and has a completely different feeling. Even when the tracks are radically different, there’s a consistency to it. Miller has a completely different sound, it’s much more down to earth than the opening track yet they both belong on the same record.

2) Songs For Swinging Lovers

Schwartz: One of the two perfect masterpieces that I’ve heard Sinatra make. It’s a masterpiece in selection, in sequencing, in arranging and singing. In art work as well, it is still stunning to behold it even from a distance as one passes through a music store.

Smith: There are a couple of Cole Porter tunes here that came from a United States Steel Hour television version of his “Anything Goes,” that Riddle arranged for the show and subsequently ended up on the album. From this album, “I’ve Got You Under My Skin” became the single most all-time requested Frank Sinatra song.

Friedwald: Sinatra’s most jubilant, up tempo album, his most successful swing record. The phrase “Swinging Lovers” is more than just a clever title, it’s romantic and rhythmic at the same time and Sinatra shows that those two ideals are not necessarily in opposition. That’s what the strength of “Swinging Lovers” is, it’s romantic and rhythm at the same time and Sinatra showed everybody how that can be done.

3) In The Wee Small Hours

Schwartz: The greatest album of music I’ve ever heard of any kind. It is relentlessly honest, understated...the melancholy arc of it, extending from Harold Arlen’s “Ill Wind,” to Duke Ellington’s “Mood Indigo,” plus the white man’s lament, ranging from my own father’s “I See Your Face Before Me,” to Jimmy Van Heusen’s “Deep in a Dream” to Hoagy Carmichael’s “I Get Along Without You Very Well.” And the centerpiece, a song written for an opera singer in 1935, Lawrence Tibbett was the guy’s name, “Last Night When We Were Young.” Tibbett sang the song for years and it was played for him immediately after the release of Wee Small Hours and he said,‘ oh, I see. ’

Smith: The first 12” album that Sinatra put together and his first theme album. Originally a 16-track album, it became a 12-track on re-release, but now on CD, it has all 16 tracks. His first recording of a Duke Ellington composition, “Mood Indigo.”

Friedwald: If you look at the ballad records with Riddle, from ’53 going up to ’58, each one gets progressively darker and darker. Wee Small Hours, is on the way to becoming Only the Lonely but at the same time, it’s much lighter. It’s more film noir than a heavy downer. Even though they are very sad songs, it’s still very much a jazz record. People tend to think that only the up tempo records are jazz records and really Wee Small Hours is as much a jazz record as anything he ever did. It covers all kinds of moods and there’s a lot of variation but at the same time, a lot of consistency. Sinatra is really the only singer who was just able to stay with one mood and stay with it for 16 tracks and never have it get tedious. Wee Small Hours is the perfect example of that.

4) Come Fly With Me

Schwartz: A very entertaining and animated work... the thematic spine of it tends to bruise the romantic notion of what an album should be because what you hear are songs about places. The album also suffers with the inclusion of “Blue Hawaii” and “The Isle of Capri” but has some formidable Sinatra moments...

Smith: Billy May’s first full album with Sinatra. True jazz, true swing arrangements. The version of “Brazil” is the definitive swinging version of the song.

Friedwald: A whole different kind of a jazz sound. When he wanted to find other avenues to explore, he decided to work with Billy May. The wonderful thing about Come Fly With Me is that it shows Billy May’s sense of humor and his sense of swing and brings out a different aspect of Sinatra. It’s much more whimsical, much more of a belly laugh. It seems much less careful, more freewheeling than a lot of the other Sinatra things yet at the same time, it’s very tightly controlled, not very much is left to chance on it.

5) Sinatra At The Sands

Schwartz: The best live album anyone has made of any kind of music. I’d like to lose the monologue for another three or four songs.

Smith: The first official live album. For me, Sinatra at his coolest here, the best on record. I love the monologues and the asides, especially where he says, “I feel sorry for those of you who don’t drink because when you wake up in the morning, that’s the best you’re going to feel all day.”

Friedwald: It’s important for two reasons. It’s his third album with Count Basie and it’s also his first live album even though he had recorded concerts prior to that but none of them really satisfied him. Basie’s presence ultimately contributed to that. On “Swinging Lovers,” Billy May’s jazz sound is more whimsical. The Basie sound is much leaner, more trim and economical. It’s interesting that Sinatra swinging means three different things when you put him with three different bands. He can fit in with all of them yet at the same time, he’s uniquely himself. The Sinatra Basie relationship, well, Basie and Sinatra suited each other perfectly because they both managed to fit into the same kind of a groove. Basie accentuates what Sinatra is doing and vice versa.

Originally published in May 1998

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