In June 2024, I bought two books about Frank Sinatra from my semi-local Barnes & Noble store: Sinatra and Me: In the Wee Small Hours by Tony Oppedisano and Sinatra: The Chairman by James Kaplan. As of writing this (late March 2026), both continue to rot on my bookshelf, their pages covered in dust and pristine spines free from any sort of crease. Here’s why:
Given that Sinatra and Me is an intimate account of the crooner’s last couple of years, I opted to read Sinatra: The Chairman first. I figured that, before I focused on the crooner’s death, I should know something or two about his life first. But the thing is, I thought Sinatra: The Chairman was an all-encompassing biography of Ol’ Blue Eyes. Well, it is, but isn’t at the same time.
See, it wasn't until I read the first couple pages of The Chairman before I realized that it was the second volume of a two-part series. Sinatra: The Chairman starts in 1954, just after Frankie won an Oscar for his performance in the film From Here to Eternity (1953). (Wait, should I have added a spoiler warning just then? Can you even spoil history books? Eh, oh well…) Meanwhile, Frank: The Voice (published five years before) begins, more reasonably, with the beginning of Francis Albert Sinatra himself. Not wanting to make another two-hour trek to Barnes & Noble again, I just downloaded The Voice onto my NOOK e-Reader and dug in.
Frank: The Voice was the best written biography I’ve ever read. Like Capote (or how I’ve heard his writing style described before—yes, I know I’m an illiterate bastard, I’m working on it), James Kaplan writes nonfiction in a beautiful, novel-like way that makes you forget that you’re reading something as intellectual and academic as a biography.
He lit both their cigarettes with a gold lighter, then paid the check. He took her hand (she kept stealing glances at his hands; they were beautiful) and led her to his car. She resisted for a moment, then she didn’t. Just a little while. (Chapter 22)
Even when things are written a bit more impersonally, Kaplan still manages to write in a captivating style. Something I’m a big fan of is his expert weaving of pop-culture through the narration, like with...
On balance, the worst that can be said about his three-part New Yorker profile (subsequently expanded into the slight but charming book The Voice) is that it was written in the amused, breezy tone so common to that magazine in those days, the verbal equivalent of Eustace Tilley deigning to glance through his lorgnette at a butterfly. (Chapter 21)
Hell, even the footnotes are a treat to read. Not only does the unessential-yet-still-appreciated information aid in a more well-rounded understanding of Frank’s universe, they’re also a great vacuum for Kaplan to quickly inject his sharp sense of humor: “The Brooklyn gangster born Giuseppe Doto had thus renamed himself, in the belief that he was as handsome as the Greek god [Adonis]. He was not” (20.1).
However, as great of a writer Kaplan is, he can’t fix how repetitive someone’s life can be—making the same mistakes over and over again and either not learning from their mistakes or not giving a damn. I wish I kept a tally for every “Frank and his wife go through a spat and then get back together” (whether it be Nancy Barbato, his first, or Ava Gardner, his second).
Another issue with The Voice is that Frank knew A LOT of people, and things kinda get on the level of War and Peace with just how many players there are in total. Agents, fellow celebrities, band leaders, musicians, relatives—you could fill several Rolodexes if you’re trying to keep up with them all! Last names are frequently repeated for the reader’s convenience, but if you’re not paying close enough attention to who’s-who, then you’ll have a hard time telling the difference between Jimmy Dorsey, Jimmy Tarantino, Jimmy Van Husen, and Jimmy Durante. (Well, maybe not the last guy—he’s that guy from the 1960’s Frosty the Snowman special.)
An “Well, yeah, of course” issue with this book? Frank was a fuckin’ asshole! A complicated asshole, but an asshole nonetheless. (Things will only get worse with The Chairman, where he starts to elbow up with Richard Nixon and Ronald Reagan. He’s a bad influence, that Bing Crosby boy!)
Overall, Frank: The Voice is a fantastic book that’s only flaws are due to its source material. It’s excellently written, intricately researched, and nice-’n’-thick to boot—it’s exactly eight-hundred pages and took me two years to finish the whole thing, hence why it might be a bit until I pick up The Chairman. However, I will definitely check out Kaplan’s other books as well: Dean and Me: (A Love Story) and 3 Shades of Blue: Miles Davis, John Coltrane, Bill Evans, and the Lost Empire of Cool. Now, c’mon, James—write a Sammy Davis Jr. book and complete the Rat Pack trifecta!
[This review was originally posted on 3/21/2026 via my Patreon. Subscribe for just $1.50 a month and get early access to not only my book/movie/TV/album reviews, but to my artwork, comics, and creative writing, too!]
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