The Songs of Sinatra

by Amanda Flinner

Francis Albert Sinatra was a skinny kid from Hoboken, New Jersey, who lived on candy bars and Coca-Colas and decorated his bedroom with photos of his idol Bing Crosby. He was a sensitive loner, a high-school dropout - and he knew he was destined for greatness. Sammy Cahn, who co-wrote many of the singer's hits, recalled: "I vividly remember sitting with him one night, and he leaned in and said with the kind of intensity that can only come from great talent, 'I am going to be the biggest singer there ever was.' I looked at him and said, 'There is no way anything can get in your way.' He reached over, grabbed my arm and said, 'You do believe, then.' Boy, did I believe." But it wouldn't be easy.

He would cultivate his famous phrasing by building his lung power – swimming underwater laps at local pools and jogging "before it was fashionable," so he could take imperceptible breaths as he crooned. Starting as a boy singer for big band greats like Harry James and Tommy Dorsey, he would become the original teen idol for the swooning masses during WWII, a movie star, and the ultimate swinging playboy. All the while, his private life was under constant scrutiny, everything from tabloid attempts to align him with gangsters, to his tumultuous affair and marriage to Hollywood siren Ava Gardner, to the harrowing kidnapping of his son, Frank Jr. Through it all, his star continued to rise, and whenever it would dim, it would only come back brighter.

As Senior Vice President of Frank Sinatra Enterprises, producer of numerous collections like Sinatra: New York and Sinatra: London, Sinatra family archivist and author of The Sinatra Treasures, Charles Pignone knows the legend of Ol' Blue Eyes, but he was also fortunate enough to know the man. In the following interview, we take a look at the history of Sinatra's influential career and how he became the greatest entertainer of the 20th century, plus that time he embarrassed himself in front of Cole Porter.

(Sinatra: London, a 3-CD/DVD boxset, was released on December 9, 2014)
Amanda Flinner (Songfacts): Before we start talking about Sinatra's songs, can you talk a little bit about how you became involved with Frank Sinatra Enterprises?

Charles Pignone: Yeah. I've been involved with him since 1984. The last 10 years that Frank worked, I traveled on the road with him, and it just evolved into a full-time job. But I originally started as running his fan club, the Sinatra Society of America, took that over in 1984. Then it just developed into a full-time job. So I was with him the last 10 years that he performed.

Songfacts: In another interview, you said you got into listening to his music from your grandfather; is that right?

Charles: Yeah. My grandfather was in the juke box business, and being Italian, Sinatra was played in the house and in the family. It wasn't until I actually saw him in concert in the '80s that I took an interest in him, and it was around the time that "New York, New York" had become a hit. I am a huge New York Yankees fan, and they started playing Sinatra, but it wasn't until I was in my teens that I began to appreciate the music and get involved.

Songfacts: By that time, there was so much information out there about his life, some not so flattering, some flattering, some true, some not true. Did you have any preconceived notions before you met him in '84?

Charles: None whatsoever, no. It was always based on the music. I just admired him as an artist and a singer.

Songfacts: Getting into the music now, he started out as a boy singer with Harry James and then moved on to Tommy Dorsey. How did that time shape his personal vocal style?

Charles: Well, I guess it's learning to be a professional. He's told many stories about how it takes several years to hone your craft, so I think it was almost like any other job: it's putting in your time and learning. In the case of an entertainer, learning what the audience wants to hear and how to go about doing your job.

There's a whole slew of singers that had huge careers coming from that era: Ella Fitzgerald, Peggy Lee with Benny Goodman, Ella with Chick Webb, Dean Martin with various bands, Perry Como. It was almost essential training for those singers to be on the road with those bands. And Frank became a bigger star than the orchestra. He made the singers more prominent than the orchestras; if you really look at the music scene in the '20s and '30s, except for Bing Crosby, the bands were the tremendous draws: Tommy Dorsey, Duke Ellington, Count Basie. So Frank contributed to the death knell of the big bands. He was the first singer that really came out of the bands into prominence.

I think there were several other factors after the war, too, especially the cost of taking 20 or 30 men out on the road. It just didn't become feasible. But I think those big band years for Frank were great training and helped sustain his career.

Songfacts: It seemed like even at such a young age - in his early 20s - he really had that innate business sense to know when the right time was to move on. He wasn't with Harry James that long before he knew he needed to make a change.

Charles: He was very lucky with Harry James because he was working at the Rustic Cabin almost as an MC and a singing waiter in New Jersey, and Harry James happened to hear him on the radio and went up to see him and offered him a job. Within a very short period of time word got out and somehow Tommy Dorsey found out about Frank and offered him the job. As he said in many interviews, Harry was very gentlemanly about it and just said, "I understand, and it's a better offer. Take it."

When he left Dorsey there was some animosity because with Dorsey, it was almost like indentured slavery. He had him to almost a lifetime contract and wanted a piece of his earnings, and then that was all settled.

By 1942, Frank Sinatra's fame had grown too big for Tommy Dorsey's band to hold, but the bandleader wasn't ready to let his boy singer go that easily. While attorneys and music execs went to battle for Sinatra, the newspapermen descended upon the singer, ready to draw blood with their pens.

Sinatra recalled in his daughter Nancy's book, An American Legend: "It began to come out of the ground that my mother went to Tommy or that the racket guys went to Tommy and convinced him that he should let me go. And that's so far afield it's scary. It's incredible."

It's the stuff of movies – which is why the tabloid tale caught the eye of The Godfather author Mario Puzo, who was penning the novel that would become a classic film. "I remember it said that Tommy Dorsey had him all sewn up. I tried to imagine how Frank would feel and think. I constructed a persona based on his legend. I made up the line 'I'll make you an offer you can't refuse,'" Puzo explained.

That's where Sinatra should bow out of the story, but lines between fact and fiction have blurred so much over the years that many think fictional crooner Johnny Fontane, who begged the mafia don to help him break his contract, is a thinly veiled Frank Sinatra. In the words of Sinatra, himself: "No way!"
Songfacts: And that unfortunately inspired a lot of crazy stories, too...

Charles: Yeah, if anybody with any real journalistic sense looks into it, they'll see it got blown out of proportion over the years - it was strictly a business deal, and lawyers and agents of Frank and Dorsey hashed it out. Frank also was represented at that time by MCA, which was headed by Jules Stein, and they controlled a lot of the broadcast links. With that they told Tommy Dorsey, "Your band likes to be played on the radio, you like to be heard by people, and if you don't come to an agreement, that might all go away."

So it was more of a business deal. He had to pay Dorsey. There are several radio shows that Dorsey appeared on with Frank's in the '40s, and they joke and kid. Then when Frank ascended and was huge and Dorsey was on the downside, Frank worked with him at his last engagement at the Paramount in 1956. So, it's all been blown out of proportion. It was strictly a business deal and that was settled. They were still friends.

I mean, Frank talked about Dorsey being a father-like figure, and Dorsey was kind of upset when Frank was going to leave the nest. They were very close, Frank and Dorsey.

Songfacts: He mentioned Dorsey was really set with his band and hated to have to train with a new singer all over again. Frank could maybe understand that later because he knew the importance of having the right musicians surrounding him, too.

Charles: Absolutely.

Songfacts: Now, one of his earliest hits was "All Or Nothing at All," which was actually a flop at first, with Harry James.

Charles: Yeah. He recorded that in August of '39, and it came out and didn't really do anything. It didn't become a hit until almost two years later during the musician strike. The musicians' union had some kind of a quarrel with the radio stations and with recordings. James Petrillo was the head of the union. For a prolonged period of time, Frank actually did some recordings with just a vocal group. There were no musicians. The musicians were on strike. Then, the label re-released "All or Nothing At All" because Frank then was popular with Dorsey, and that's how that became a hit.

That was a song, though, that he would credit as his first hit. He would do it over the years in different forms - as a ballad, and then on the Strangers in the Night album as an uptempo thing with a Nelson Riddle arrangement. It was a song that he continued to sing up until he retired in 1995. It came in and out of his concert repertoire through the years, and he always spoke of it very fondly.

Songfacts: Another one he recorded several times was "Night and Day."

Charles: The story with "Night and Day" is he was singing at the Rustic Cabin, and he was told by one of the musicians that Cole Porter had just walked in. To impress Cole Porter, he said to the guys, "Let's Do 'Night and Day.'" He was so nervous that he proceeded to forget the words, and he was embarrassed, but I think Cole Porter was very gracious about it.

In later years Frank would say that when he got to know Cole Porter, Cole Porter would kid him about that and say, "I remember that night when you forgot the words to 'Night and Day.'"

But "Night and Day," his first recording of that was in 1942. That's when he was ready to leave Dorsey and he got a chance to do four sides as a soloist on the Bluebird label. He did "The Night We Called It A Day," "Lamplighter's Serenade," "The Song Is You" and "Night and Day." Those last two songs, "The Song Is You" and "Night and Day," those are songs that would stay with him throughout his career.

"Night and Day" is really the quintessential song for Sinatra because it's one he sang throughout the decades with different types of arrangements. It's a very lush arrangement in the '40s where he's crooning, and then when he does it in the '50s with Nelson Riddle, it's an uptempo arrangement. Then in the '60s, he did it again as a ballad with Don Costa on Sinatra and Strings, and then in the '70s he did it as a disco arrangement by a man named Joe Beck. It's more readily identified with him than I think with anybody else. He also used it on his radio shows in the '40s as sort of a theme song.

He would even sing it in concert on his Diamond Jubilee World Tour in the '90s, so that's one of the few songs that stayed with him for decades, that he just had a certain affinity for. When you think of "Night and Day," you think of Frank Sinatra.

Songfacts: This would just be speculating, but would he have sentimental value for that song because he started out with that night at the Rustic Cabin before he was even famous?

Charles: Well, I can't really speculate. I know in talking to him over the years about certain songs. I would say with this song, the audience loves it. Frank said to me once, "I know what it means to everybody, but how do you think I feel about these songs? What do you think they mean to me?"

I think the songs meant a lot to him, I think there were certain songs over the years that he probably had an affinity for, and I think "Night and Day" was one of them. I think that by doing it differently over the decades and knowing what the audience wanted, that's why he was able to sustain such a long career and be on top for so long.

Songfacts: His popularity really exploded with the teenagers during World War II, but he was unable to enlist because he had a birth injury to his eardrum. Do you think that "The House I Live In" was one of the ways that he was contributing to the war effort?

Charles: I think "The House I Live In" had more to do with racial inequality and bigotry. Frank was always on the forefront of that. Songwriters approached him, and as you know he did a short film for RKO, and then he won a special Academy Award for that.

"The House I Live In," that's another one of the songs like "Night and Day" that he had an affinity for. He would do that throughout his career. He sang it at the inaugural he produced for John F. Kennedy, and he would sing that every decade of his career. I remember him singing that in the '90s during the first Gulf War. That was another song that just stayed with him throughout his life, so I'm sure he had an affinity for that. Frank actually would tour high schools around the time because of the problem with segregation in this country.

By the time "The House I Live In" was done, the war was coming to an end. This was, I think, May of '45 when he did "The House I Live In," so I think Germany had or would within a couple of days or weeks surrender. The war was practically ending, and in a few months Japan would surrender, so it's really not anything to do with World War II. It's more about racial intolerance and bigotry in the country.

Songfacts: Nancy Sinatra mentioned in her book that the RKO short was really his special project. He brought everybody together to do it, and it was really important to him.

Charles: I'm sure it was. If Frank hung onto a song and sang it for 5 or 6 decades, I don't think it's a throwaway song. I think it had to mean something to him. That's getting back to what the X factor is that made him so popular and made people gravitate to the voice. Frank always said when he sings, there's honesty there. He's honest. So I think that if it wasn't a song that he had an affinity for, he would have done it, and then it wouldn't have appeared again. The man recorded over 1,000 songs, a lot that never made it into his concert repertoire. He also made a lot of concerts and a lot of TV shows, so I do think that he, in picking the songs that he would do for his shows, must have had favorites, and I think "The House I Live In" was one of them.

Songfacts: Because he did pour that much emotion into his songs and brought so much honesty to them, were there any that were emotionally difficult for him to revisit later?

Charles: Well, he's known for, as he called them, saloon songs, or torch songs as they were known before. It would usually in the later years be "One For My Baby" or "Angel Eyes," and he would do them with his pianist, Bill Miller. They're classic recordings. There's also "In The Wee Small Hours" and "Guess I'll Hang My Tears Out to Dry" from Only the Lonely.

Yeah, I do think when he got older, emotions would well up when he was singing a song. It's a lot different if you're a man in your 40s singing those songs, and then you have a different view of it when you're in your late 70s. There were many times in the later years where he would get emotional. I remember sometimes he would tear up after "The House I Live In." I think some of these songs were very emotional for him.

Songfacts: Can you talk a little bit about the story behind "Nancy (With The Laughing Face)"?

Charles: "Nancy (With The Laughing Face)," Jimmy Van Heusen wrote the music and Phil Silvers wrote the lyric. Silvers was a comic and a friend of Frank's who went on to do a lot of movies, like Mad, Mad World. I don't know how many people remember him today, but he's probably mostly known for Sgt. Bilko in the '50s. The story is that Van Heusen had written the song for I think Gene Kelly's first wife, or somebody's first wife, and it was called "Bessie With The Smiling Face" or something like that. Van Heusen was a pianist/songwriter and was friends with Frank, and I think at one point Frank heard him noodling on the piano and asked him what that was. Frank was with Phil Silvers, and he played it, and they made a bet. Phil Silvers said, "I bet that you if you give me a day I can write a better set of lyrics to that and I'll write it in honor of Nancy," Frank's daughter. So that's how that happened.

But the melody of that song had been written before with Johnny Burke, who was working with Van Heusen at the time. They had done it as a song just privately because back then the Hollywood groups would have parties, and they would put on shows with actual talent. Frank actually would do this at his Toluca Lake house where Sammy Cahn would write songs, and people would get up and sing. So the melody of "Nancy" was written prior to that, and then Phil Silvers put the lyrics on for Nancy.

Songfacts: There was a story floating around that I think Johnny Burke had said that Frank got really emotional at the party and started crying, thinking that the song was specifically written for Nancy. Then they didn't want to tell him that it wasn't really. But I didn't know if that was true or not.
Frank Sinatra on prejudice: "Prejudice is nothing new to me. In Hoboken, when I was a kid, I lived in a tough neighborhood. When somebody called me "a dirty little guinea, there was only one thing to do – break his head. When I got older, I realized you've got to do it through education – maybe with a few exceptions."

- Frank Sinatra: An American Legend by Nancy Sinatra
Charles: Well, if it's from a credible source of Johnny Burke's, it might be true. But the way I've heard it and the way Frank Jr. tells the story is that Phil Silvers came in and said, "I can write a better lyric than that, give me a day." I'm not sure whether they surprised Frank and said, "We're going to write this for Nancy," or Phil wrote the lyrics and then played it for Frank and surprised him.

Songfacts: Now a lot of people assumed that Frank was the one who wrote it. In your Sinatra Treasures book, there's a quote from him clearing that up.

Charles: Yeah, there are a lot of misconceptions. A lot of people still to this day think Frank wrote "My Way." I think it was because he was so convincing as a singer. What people don't understand, it wasn't really until the late-'50s or early-'60s that the craft of songwriting changed. The whole tide changed. You had people like Johnny Mercer or Cole Porter, and their job was to write songs, not sing them. Then when you move into the Bob Dylan and the Beatles era, they figured, "We'll write them and we'll sing them."

It's debatable - but I don't think most people in the music business would debate it - but the quality of songwriting dropped immensely because it's like anybody else doing a job; if you're a plumber, you're not an electrician. Most of these people that wrote songs are not great singers.

A lot of people, because Frank was so convincing in what he sang, thought he had his hand in writing a lot of these songs. He did write a few songs and he's contributed lyrics to some songs, like "I'm A Fool To Want You." I do think it's a testament to his artistry that a lot of people think that he wrote a lot of these songs, which he didn't. But he grew up in the era where songwriters, their job was to write the songs, not sing them. Then there was a huge sea change where groups and artists decided, "I can write a song with a few chords and record it, and then I don't have to share in the publishing." So the people that their craft was just songwriting, they were sort of kicked to the curb.

Songfacts: The lyrics were extremely important to Frank. He said a few different times that he really focused on the lyrics when interpreting a song, more so than even the music element of it.
Sinatra on lyrics:

"I always believe that the written word is first, always first, the word is first. Not belittling the music behind me, but it's really a backdrop, a curtain actually. I think a lot of singers through the years that I've been in the music business, they never quite learned about reading a song properly. Look at the lyric and understand it, find out where you want to accent something, where you want to use a soft tone. The word actually dictates to you in a song; it really tells you what it needs."

- Interview with Arlene Francis, 1981.
Charles: Without question. He said that throughout the years, that he would look at the lyrics to try to figure out what the songwriter was trying to write and how he could breathe life into the song. I think there's no question about it.

Songfacts: In that respect, can we talk more about "I'm A Fool To Want You," which he was credited as a songwriter? That supposedly came from an emotional recording session.

Charles: Yeah, I think what happened was it was a tough period in his life. He was going through some personal problems with Ava Gardner and with his first wife, Nancy, so I'm sure it was a very emotional time for him. I wasn't there, but the story is that when he got the song he made some suggestions and changed some lyrics and did that song, and supposedly got very emotional when he did it.

I think there's a story, too, that he did that and left the studio. I'm not sure how true it is because looking at the session sheets on that, he would do another song after "I'm A Fool To Want You" at the session. Sometimes these stories get handed down. Without talking to a person that was actually there or talking to Frank about it, it's hard to say. But I do think that was a very emotional song for him, and if he was given credit for the lyrics, he must have contributed something that the songwriters felt was viable and contributed to the overall quality of the song.

Songfacts: Now, from his solo debut album, which was The Voice of Frank Sinatra, you singled out his rendition of "These Foolish Things."

Charles: Yeah, I just put that in because I was listening to it at the time. We're putting out a set called Live In London, and he does it in 1984 in London, and he said, "Here's one of my very favorite songs of all time." It's one of many that he did over the years. Another one that he always used to say, and didn't do that often in concert, was "Laura," the David Raksin and Johnny Mercer song. He recorded that a few times. But specifically, I can remember him saying in concerts it was one of his favorite songs.

But there's not much I can tell you about "These Foolish Things." I think there are much more interesting stories on the other songs.

Songfacts: Did he listen to his own songs very much?

Charles: Oh, I'm sure he did. The kids would say that he would bring home acetates of the sessions that he did and he would listen to them.

Songfacts: When he made his comeback in the '50s and reinvented himself as the swinging kind of playboy, one of his favorites was "Come Fly With Me."

Charles: Jimmy Van Heusen and Sammy Cahn - Jimmy was one of his closest friends for many years - they would write the title songs for a lot of these concept albums like Only the Lonely or Come Dance With Me. The idea was an album about traveling, and they wrote "It's Nice To Go Traveling." So they wrote "Come Fly With Me" with him in mind. I think that epitomized that decade and the good life and having a good time. America was just picking up the pieces from World War II, and the decade before that they were in a war, and things were changing in America. That that song caught on and that was one of his most popular albums.

That's another song he continued to do till the end of his career. I think he recorded more Sammy Cahn compositions than anything else. They were almost like his personal songwriters, Cahn and Van Heusen. Before that, Sammy Cahn had written a lot of songs for him with Jule Styne and prior to that, Jimmy Van Heusen had written with Johnny Burke a lot of the Crosby stuff, and Sinatra had covered that stuff at Columbia.

Essentially, Frank put Van Heusen and Cahn together, and they wrote tons of hit songs for Frank. Knowing his personality and knowing him as well as they did, that's why a lot of the songs they wrote just seemed to fit him perfectly; they were written with him in mind.

Songfacts: And he really went to bat for Sammy Cahn at MGM before he really became known as a songwriter.

Charles: Yeah, for Anchors Aweigh. Frank was just new to MGM, and Sammy Cahn tells the story that MGM offered him anybody - Jerome Kern, Johnny Mercer, the cream of the crop - to write the songs for the movie. He said, "I want Sammy Cahn," and they said, "Who?" Then I think one of the producers told Frank no, and it caused a big to-do. In fact, I think Lou Wasserman - who then was a Hollywood icon, he was an agent back then - personally called Sammy Cahn and said, "You've got to talk to Frank and you've got to get him to back down. I'm not sure if MGM will kick him off this picture." The quote is that Frank called up Sammy Cahn and said, "If you're not on the set on Monday, I'm not going to be there."

So Sammy was always indebted to Frank; I think that's a quality that anybody that knew Frank personally or knows about his career, that loyalty was something. And Frank didn't have a lot of clout. He was new to the movie business back then but stood up for Sammy Cahn. I think that's something that Sammy Cahn never forgot. Love to tell that story. I think it tells you all you need to know about Sinatra and loyalty to friends.

Songfacts: There was another story that Sammy Cahn told about "All The Way."

Charles: Oh, about them rehearsing that.

Songfacts: Sammy Cahn had somebody with him who thought, by his reaction, that Frank hated the song.

Charles: Well, Sammy was quite a raconteur. I mean, I've heard Sammy tell the story about that. They wrote that for the movie The Joker's Wild. I think they went up to the Sands Hotel, and Frank was working there. Frank said, "Show it to me during breakfast," and Sammy's joke was, "Who knew breakfast was at 4 o'clock?" Because Frank had just gotten up. So, yeah, there are a lot of great stories.

Songfacts: Another one from a movie is "Luck Be A Lady," which was sung by Marlon Brando in Guys and Dolls.

Charles: Right. Frank always lamented that he didn't have the Marlon Brando role, which he should have had because the songs were more adaptable to Frank. Brando couldn't really sing. Frank would always joke about that. Through the years he would do "Luck Be A Lady" again in concert.

In talking to Billy May about that, when Billy May originally had written the orchestration for Frank, he had done it as it's done in the movie and on Broadway, in the same tempo. Frank was the one that told him, "No, I want it different." That's another song that through the years everybody just associates with Frank and just assumes, if they had never seen Guys and Dolls, that he sang in the movie. He had a nickname for Marlon Brando, he called him Mumbles, but he would always preface the song in concert by saying Brando sang the song in the movie and that he's "Not a great singer, but probably the greatest actor ever."

When you hear "Luck Be A Lady" and how it's done specifically in the play, Frank was the one that told Billy May how to arrange it and changed the tempo a bit so it would be different. Of course, it fits Frank like a glove.

That's another great quality about Frank. You had mentioned that about with Dorsey, but Frank had this innate ability with these arrangers. Axel Stordahl was great for him when he was crooning with that lush thing, but then he got very lucky with Nelson Riddle. But Frank originally, when he first went to Capitol Records, had known and always wanted to work with Billy May. Billy had done some radio charts for him in the '40s on Hit Parade when Axel Stordahl needed somebody to ghost him.

When you listen to a lot of singers from those days, nowadays the arrangements sound dated. When you hear a lot of Frank's stuff, though, it sounds like it could have been recorded last week, just because he had that ability - and he did. Listening to interviews with Nelson Riddle, Nelson would say that Frank would practically lay out how he wanted the arrangement, and that's why the arrangers would always say that there's not a lot of arrangements over the years that he turned down.

That was one of the questions that almost everybody would ask Nelson Riddle, Billy May, or Don Costa: Did he ever say, "I don't like this arrangement"? Very rarely, because he would kind of map out and tell them what he wanted. In fact, Nelson Riddle has a pretty funny quote where he was saying, "I stayed with Frank so long because I had great secretarial skills and that's because we would sit down months before an album, and he would lay out the album and pick the keys with Bill Miller but then tell me specifically what he wanted in there. When we came to the session, I, taking for granted that he didn't forget - which he didn't - and I had done what he said, and he was very happy with that."

Songfacts: One thing we kind of mentioned, but I skipped over a little bit, as far as one of the ways he's incredibly influential was that some of those albums like In The Wee Small Hours are credited as being the first concept albums. I don't know if a lot of people know that.

Charles: Yeah, Frank is the artist that came up with the idea. Again, this is all about with timing. He was very lucky that they were able to go from the 10-inch to the 12-inch, but he had envisioned that instead of people just making singles, to do a whole album thematically so it would hold people's attention. It's all changed now because everything's digital or on an iPod, and people shuffle it. You have to remember what a revolutionary concept - pardon the pun - it was because I think Frank felt that when people would drop that needle down, there's 15 or 18 or 20 minutes on one side, and it's pretty jarring if you're all over the place with a ballad, then a tempo song. He really came up with the idea of doing these concept albums where they thematically, musically and orchestrally would fit together, and a lot of work went into that.

People hear them now and take it for granted. I've heard people compare Frank to Fred Astaire: when you see somebody like Fred Astaire dancing; it looks so effortless, and you think maybe you could do that. It's like with Frank when you hear him sing, you sing along with him, but if you take his voice away and listen to yourself, it's not that flattering.

I think he worked at his craft and worked on these projects so much that it seems like anybody could do it, but there was a lot of effort put into it. That's why those albums are considered classics today, such as In The Wee Small Hours or Only the Lonely or, as we said, Come Fly With Me. Because they just stand up. They're just real quality. The songs on them, the arrangements and the singing.

Las Vegas in the early-'60s was all about the Rat Pack, a group of entertainers and friends that included core members Dean Martin, Sammy Davis Jr., Joey Bishop and Peter Lawford, with Frank Sinatra at the helm. (The name originally referred to actor Humphrey Bogart's circle of friends that congregated in California's Holmby Hills.) Aside from filming classic movies like Ocean's Eleven in the Sin City, the group unleashed their antics in nightclub acts, with musical numbers and both scripted and spontaneous comedy routines, to packed audiences for two shows a night. Whenever one name was on the marquee at The Sands, you could bet that a few others would show up to crash the party. With just a handful of films and few live recordings in existence today, the Rat Pack's chemistry and genuine camaraderie has made them larger-than-life.
Songfacts: I'd be remiss if I didn't mention the Rat Pack. Did he envision that becoming as huge as it was or was that just designed to be publicity for the Ocean's Eleven type movies that came out?

Charles: I don't really know. I know that Frank with Dean and Sammy, he considered them like brothers and he loved them. I think that's why the act was so successful. But in the career of Frank, really when you look over it with a fine-tooth comb, they didn't do that many performances, and they didn't do hardly any recordings together. There's We Open In Venice with Frank, Sammy, and Dean from the Reprise repertoire, but they got together when they were filming Ocean's Eleven and the act became very successful. They did engagements in 1960, and then they did some dedicated engagements in '63 when they were still making movies, but it really kind of disbanded around '64 or '65.

After they made Robin and the Seven Hoods, they were all on stage again with Joey Bishop, but without Peter Lawford in '65. Then Frank, Dean, and Sammy would do some benefits through the years sporadically, and then Frank in 1988 decided to get the Rat Pack together again.

He never liked the term the "Rat Pack." Originally it was called The Summit at the Sands based on the Krushchev summits, what was going on in the world back then in 1960, but the press dubbed it the Rat Pack.

In 1988, Frank revived it and convinced Dean Martin to go back on the road. Dean had lost his son in a plane accident, and Frank thought, to pick up his spirits, let's do a tour. So they devised a worldwide tour, called Together Again. Unfortunately, Dean only did the first six dates and then bowed out of the tour because he just was not in the shape or mindset to play arenas. He had never played arenas. At that point, Frank was playing huge arenas and theaters and Dean was just used to playing the showroom in Las Vegas. It just got to be too much.

Frank and Sammy then continued the first leg of the tour and when the tour resumed, they slotted in Liza Minnelli, and the tour became known as The Ultimate Event. For all intents and purposes, 1988 was the last time they performed together. After '63, they really didn't do much. There's just not a lot. The myth of the Rat Pack is greater than the amount of work they actually did.

Songfacts: It seems like there should be so much more just based on the memorabilia you see all the time and the references.

Charles: Well, I don't know how you would equate that today. I mean, these guys were huge superstars. Sammy was a Broadway star, Frank had him in the movies. Dean was a huge star, just coming off the comedy team of Martin & Lewis. They were the top draws around the country in cabarets and concert halls, and especially in nightclubs, when there were nightclubs.

The closest I ever thought it came was when Elton John and Billy Joel did a tour about a decade ago, but they were not in the pinnacle of their careers. These guys were all huge at that point. Today, nobody's fame lasts as long as it has for these other superstars. You can't have a career like that.

I think it was the aura of getting these huge superstars together. Plus, the Copa Room sat less than 1,000 people, so you had to be very lucky to get in and see them. It's where everybody wanted to be. I think it helped Las Vegas and just that aura of the Rat Pack, that fun and camaraderie and hanging out. Everybody tries to emulate it, but nobody has captured that magic.

Songfacts: Two of the biggest songs Frank Sinatra is remembered for are "Strangers In The Night" and "My Way." The stories are that he hated both of these songs, but did he really hate them that much?

Charles: It's very clear, he would say on stage that he did not like "Strangers In The Night." You sound like you've done your homework, but you'll read Jimmy Bowen is the one that sort of hipped Frank to the song and had a quick arrangement of it done. They did the recording session, and then Jimmy actually pressed some acetates and sent them out to disc jockeys. He actually paid stewardesses in certain cities to take these acetates on a plane, then drop them off at a city to disc jockeys because he was aware that Jack Jones had recorded the song and he wanted Frank to get airplay on it.

It got a great response. That was recorded April 11th, '66, and within a month he was back in the studio with Nelson Riddle. So when you listen to the album Strangers In The Night, except for the title track, which Ernie Freeman did the arrangement, everything else in the Strangers In The Night album is done by Nelson Riddle.

They built an album around a successful single, but Jimmy's whole concept of that was, "Let's do this song as a single," and it just took off. Then they did an album on it.

Yes, he said it many times, he was not a fan of the song, but this is that innate ability of Frank knowing what the audience wanted. He would do that again in concert, it would come in and out of his repertoire and a lot of times he would joke with the lyrics. He would say, "I hate this song, I detest this song," but he would do it because the people wanted to hear it.

Songfacts: From what I've read, he seemed to think "My Way" was just too self-indulgent.

Charles: That was one of the songs people thought he had written, and he would say sometimes he thought it was too on the nose, and he thought people associated that with him. The story is that Paul Anka had heard the song, which was originally a French song, and all he did was adapt it, put new lyrics to it, and got it up to Frank. Paul Anka had an association with Don Costa, and in the '60s Don worked a lot with Frank. When Anka started out, Don was his arranger and helped him.

Through the influence of Don Costa and Anka, they got Frank the song. I guess Bill Miller or somebody played it for him up at Caesar's when they got the music, or he listened to a demo of it. Then December 30th of '68 he went in again; that's another song where he went in, and it was done as a single. Then because of the success of it, they built an album around it.

I think also that is the one song that people would always yell for and clamor for, and he would joke about it, too. I don't think he hated it as much as he disliked it. I don't think he hated any of these songs. I just think he may have gotten tired of people yelling for it and singing of it. It's a fan favorite, but I wouldn't say it was a Sinatra favorite.

Songfacts: That was one of the songs Bill Miller couldn't play on because he hurt his hand during the recording. He cut his hand on broken glass.

Charles: Yeah, Lou Levy worked with Frank on "My Way." Lou was a great accompanist. He worked with Peggy Lee, Ella Fitzgerald for years, and he even came back and worked with Frank in the late '80s. Frank used to hire him to play at parties at his house. Lou was a great jazz pianist. At that session Bill didn't play. Bill conducted the orchestra.

Songfacts: Do you think that there's a song that would better represent Frank Sinatra than the ones that he's remembered for?

Charles: I think he's remembered for so many songs. If the question is should he be remembered for the hits, like "Strangers In The Night" and "My Way," I think that's a disservice to him. I think it's great to have hit songs, but I do think that if you delve deeper into the catalogue, you will hear better recordings. For instance, if you wanted an uptempo, "I've Got You Under My Skin" or "Come Fly With Me." Or if you wanted a ballad, "In The Wee Small Hours" or "Guess I'll Hang My Tears Out To Dry."

So it depends on how you frame that question. If you're saying his greatest successes and you're going to base it on record sales, like "My Way" or "Strangers In The Night," yeah, I think if people delve deeper, there's probably a lot better representation of what Frank Sinatra is and was and why he is so important to music and still relevant. But I don't think anybody would discount having songs that connect with the public, but he's got such an immense catalogue that it's hard to pigeonhole certain songs.

Songfacts: As a fan, it can be frustrating when somebody only associates him with the big ones, like, "Oh, Frank Sinatra, oh, yeah, he sang 'Strangers In The Night.'"

Charles: That's when you tell them go buy Only the Lonely or give them a copy of Wee Small Hours. It's good that he's known for certain things and people still know him, but with any artist that had a career like his, there's a lot more if you scratch the surface.

If you're a new fan, there's so much to discover. There's just such a great catalogue of material and almost all of it, 99 percent of it, has been released on CD, digitally or vinyl. It's not like other artists. A lot of Frank's stuff is still in print, so you can still go out and listen to it, and it's there for everybody and for future generations.

Songfacts: And of course his films are out there, too. We didn't get to talk about that very much, but he definitely had a great film career, as well.

Charles: Yeah. He starred in a lot of films, starred or co-starred or even had cameos in over 60 films. He was nominated many times and has won three Academy Awards: one for The House I Live In, one for From Here To Eternity [Best Supporting Actor, 1953] and the Jean Hersholt Humanitarian Award. Anybody today would be considered a superstar just with his film career.

So when I say to people they don't understand the enormity of this guy's career, it's hard to believe how he did all of it. If you took his movie career success standalone, today that would be equivalent to somebody who's considered a huge superstar. He had a multifaceted career, and thank God he did. It was great.

Songfacts: You'd be hard pressed to read of anybody of importance in the 20th century and not hear a mention of Frank Sinatra somewhere. He was connected to so many people, in and out of entertainment.

Charles: That's a good point. I don't think there's anybody in the world who hasn't heard the voice or heard the name, and he's so connected. I think besides the quality of what he did, that's one of the reasons he lives on. It's not just nostalgia. People's parents or grandparents had listened to it. They heard it or were exposed to it in the house, like I was. A lot of the 20th century, he was played on the radio. There was exposure on the radio or on television, so people were able to hear him.

He is the defining voice of the 20th century, there's no question about it. People think of America, and they think of him. He's the quintessential American singer and he did tour the world. I think he was an international superstar besides the music because of the movies. It's an enormous career. I don't think it will ever be equaled in terms of the quality of the recordings that he has done over the years.

It's amazing that even the last recordings he did, the duets, how well they sold. That has spawned, up until today, Barbra Streisand doing the superstar duets and Tony Bennett making a whole second half of his career out of it. I think Tony, in the last 15 years, if he's done eight or nine albums, 70 percent of them are duets. Frank started that trend of the superstar duets in the '90s and it continues to this day. He always was the leader, and it's nice to see that he still is.

November 14, 2014. Find all the latest Sinatra news at
Photo courtesy Frank Sinatra Enterprises

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Comments: 3

  • Jim S from West Chester, PaGreat read! Greater talent. I’m 81 and I remember most of it and enjoyed (still enjoying) all of it, that I remember. He brought immeasurable pleasure over many decades.
  • Rob Balton from Dingmans Ferry PaThank you! This was wonderful!
  • Larry Uelk from Moline, IlGreat story about Sinatra! I saw him at his lat appearance in St. Louis. Been a fan all my life. Vis a vis Night and Day: Sergio Mendes had a great version as well with Brazil 66.
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