Sinatra: The Chairman is the second volume of James Kaplan’s epic biography of Frank Sinatra, following 2010’s Frank: The Voice. It’s a comprehensive look at the second half of Sinatra’s life, exploring his works as a musician and actor, and giving a rich sense of the complexities and contradictions that drove him forward. It begins in the aftermath of Sinatra’s Academy Award win for his work in “From Here to Eternity,” and proceeds through the decades, giving a full sense of his methods and the turmoil that he both contended with and created.
We spoke with Kaplan about the process by which these volumes were created, the challenges of researching events from the middle of the 20th century, the underrated moments of Sinatra’s vast career, and more.
Biographile: You’ve now released two volumes of a biography of Frank Sinatra. What initially drew you to him as a subject?
James Kaplan: Well, there’s a circumstantial answer to that question and there’s a deeper answer to that question. The circumstantial answer is that I had done a book with Jerry Lewis. I wrote his memoir, Dean and Me: A Love Story, back in 2005. Jerry talked a lot about Sinatra. A lot. I did a lot of thinking about Sinatra as I was interviewing Jerry Lewis for his book. That was part of it.
The next thing that happened was, as I was finishing the book, Jerry — who used to run the Muscular Dystrophy Telethon — invited me to the Telethon in 2004, which was in LA. While I was out there, I went out to dinner with a bunch of the musicians who were working on the show. We had a very fun and boozy dinner, and everybody was in fine spirits. Sinatra came up, and I felt as though, great, here comes some great Sinatra gossip from these guys whose inhibitions are down. Instead, their voices lowered and they talked about what a musical genius he was.
Right around the same time, a new biography of Sinatra came out, and it was kind of the same thing that had been done before: the gossip, the Mob, the women, the fistfights. The review in the New York Times said, “the definitive biography of Sinatra has yet to be written.” I had been trying to think of a next book to do. I wanted to do a big book about a big subject. I grew up in the 1950s and 1960s, and Sinatra was really part of the fabric of my life back then. He was in the air, on the air — you heard him on the radio, you heard him when you walked into a store and you heard a Sinatra song playing. He was playing all the time. But beyond Sinatra himself — I should say that the dinner with those musicians gave me the idea that it could be very interesting and new to write about Sinatra as a musical genius, as opposed to Sinatra as a figure of fun or a figure of gossip or a guy who got into a lot of fistfights and had a lot of love affairs and hung out with mobsters.
I wanted to write a big book about that genius, but I also wanted to write a big book about the American century. Sinatra was born in 1915 in Hoboken, New Jersey, when there were still cobblestones and horses on the street. The night he died, May 14, 1998, was the finale of “Seinfeld.” So there you have quite a stretch of American history, and quite a lot to write about. Sinatra’s was a life that touched on almost aspect of American life throughout that very long lifetime and long career.
BIOG: Before reading your book, I hadn’t realized that Sinatra and Quincy Jones had worked together. Was there anything else that you learned about his work as a musician that surprised you?
JK: Sinatra is a constant revelation. The thing that I learned in the first book, and that continued to astonish me in the second, was how incredibly hard Sinatra worked on his singing and his recording. It meant everything to him. Even though it sounded utterly natural, it wasn’t. He would go into training before recording an album, cut down on the cigarettes, cut down on his drinking, try to get a little more sleep. Whenever he learned a new song, he studied the lyrics as if he was reading a poem. He knew those lyrics cold before he even sung a note of music. That helped him give the feeling that he really lived inside that song when he sang it. His breath control is legendary; that was something that he worked on. He used to swim laps underwater in a swimming pool. That was a big musical revelation to me in the first book, and it continued to be in the second book.
In the second book, the astonishing thing is how he continuously reinvents himself from great album to great album. In the Capitol years, and then in the years of his own record label, Reprise. There are so many great albums. Sinatra did a couple of amazing and gigantic things, as far as American popular music was concerned. In the early 1950s, on his late albums for Columbia and his early albums for Capitol, he really introduced the idea of the standard — the works of Gershwin and Rodgers and Hart and Irving Berlin and Cole Porter; so many great songs and great songwriters. It seems like such a given these days, but it wasn’t a given back then. Sinatra revered those songwriters, and brought those great songs to the fore by insisting on putting them on his albums. He made great art out of them.
The other great invention of his was the concept album. There wasn’t really quite such a thing before Sinatra came along and decided to give each of his albums a distinctive mood and theme. From album to album, especially throughout the Capitol years, he was creating a new invention every time out. It was thrilling every time.
BIOG: You also talk about his awareness of contemporary composition, which I found very interesting.
JK: Not only contemporary composition. He had amazing ears. He had vast musical knowledge, and vast musical appreciation. Classical music — the work of Ravel, the work of Ralph Vaughan Williams, even such an esoteric composer as Reinhold Glière, Debussy… He loved the French Impressionists. He listened very deeply and very widely. He knew instantly whether anything was worth listening to or not. I should also add along with that that he had a huge appreciation, from the very beginning of his career, practically when he was a teenager, of the giants of American jazz. He used to frequent the nightclubs on 52nd Street in Manhattan, and learned from an early age what great, great musicians Billie Holliday, Lester Young, Teddy Wilson, all these regal figures of American popular music [and] jazz were.
BIOG: When you were looking back at his albums, were there any that you found that seemed underrated or which hadn’t really gotten their due?
JK: People tend to pick the usual suspects when they talk about Sinatra’s great albums. They talk about In the Wee Small Hours, which is a titanic album. It’s impossibly great. But I would say that there are quieter albums that he did in the 1950s. Albums like Come Fly With Me and Come Dance With Me, people love those, and justifiably so; they’re great albums. The great Billy May albums, the brassy albums, the swing albums, and the Basie albums for Reprise: Sinatra-Basie: An Historical Musical First and It Might As Well Be Swing. There are so many great ones… Some of the quieter ones: Sinatra and Strings, All Alone, both Reprise albums; and earlier, Close to You, Where Are You, No One Cares, the suicide album. These albums all get talked about from time to time, but the higher-profile ones get more ink.
BIOG: Sinatra: The Chairman includes interviews with contemporaries of Sinatra and their children, along with accounts from memoirs and newspapers. What was your research process like for the book?
JK: Well, I began this gigantic process as an ignoramus. I knew next to nothing about Sinatra. All I knew was that I wanted to write about him. I knew something about his music. I began to have to listen to everything. Everything. Everything. Not only all of the albums, but many of the outtakes from his studio sessions. I had to read everything about him–the biographies, the music books, biographies of people who touched his life. And, of course, I had to begin to interview. The research: there was music; that was one component. There were books; that’s another component. To a huge extent, I tapped newspaper archives in both volumes. Gossip columns were very important to both volumes. The newspaper archives were key to my research. And then interviews.
A big difference with the two volumes was that, in writing about the very early part of his career, of necessity, I had fewer people I could interview than when it came to the latter part his career. I was extraordinarily lucky, in the first volume, to be able to catch, before they left us, people like Bill Miller, who was Sinatra’s longtime pianist, accompanist, and the great keyboard player on “One for My Baby (and One More for the Road).” That arrangement is Bill Miller’s. I was able to talk to Connie Haines, who sang alongside Sinatra in Tommy Dorsey’s band. When I got to volume two, which begins in 1954 and goes until 1998, I had a myriad of people that I was able to interview so the process was somewhat different.
BIOG: Did you know from the outset that this was going to be a two-volume project?
JK: No. My initial contract for the book said, “A life of Frank Sinatra. 352 pages.” I did two years of research — reading, listening, interviewing for the first volume before I began writing anything. It just became very clear to me very early on that I had taken on…not only this giant figure with a sixty-year career, but I had taken on the American century, the 20th century. It’s a huge amount to take on. About halfway into the first volume, it became clear to me that I had bit off a lot. Not necessarily more than I could chew, but more than I could chew in one book. When I came to a natural break, which was his Oscar for “From Here to Eternity” in March of 1954, it seemed like such a good inflection point. It seemed like a point where he was just beginning to come back from the terrible career tailspin he had after World War II. But all of the great Capitol music and Reprise music and his career as a movie star–all of that was really in front of him. The one very important person who I was able to talk to before they died was Jo Stafford, the wonderful singer who also sang alongside Sinatra in the Tommy Dorsey Band.
BIOG: This book is very factually rich, but there are also certain moments where multiple versions of certain events, where a definitive record doesn’t exist, are described. How did you settle on that approach?
JK: This is the core problem of biography. Certainty is, ultimately, impossible. If you think about your day yesterday, anything that you did that involved anybody else would involve multiple viewpoints and multiple interpretations. Your memory might be faulty, even one day later. To construct a cogent narrative, you have to take on as many perspectives as possible, and then ultimately, based on your intuition and on your reading and on your knowledge, make your best guess. I don’t mean to make it sound haphazard, but writing biography is a subjective art. It is the craft of a writer who is looking at as much evidence as possible and deciding how to tell a story. Yes, there are ambiguous situations. I try in both volumes, when there’s less certainty — when there’s ambiguity, I try to indicate that. I try to tell a story with some authority, and I really tried very, very hard to triangulate. That is, I tried to read everything written about every incident in Sinatra’s life to try to figure out who made mistakes before, to not make those mistakes again. To try to get it as right as possible.
BIOG: You worked with Jerry Lewis on a book, and you now have these two volumes about the life of Frank Sinatra. Are there any other figures from that era who you could see yourself writing something about?
JK: I don’t think so. I think I’d like to do something different next time around. I think it’s very hard to follow Frank Sinatra. Jerry Lewis — Jerry is the last dinosaur, really. He is the last gigantic figure from that age who still walks the earth, God bless him. Sinatra is such a great figure, such an artistically great figure and such a culturally significant figure, he’s a very hard act to follow. I don’t think that I would want to go back to that same period, that same milieu, and look at other figures. Nick Tosches has already done a wonderful book about Dean Martin. Dean Martin has always been fascinating to me, but I think that Nick Tosches really did it. I’d like to go someplace else, maybe another era, for my next book.