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Sinatra in Fiction: 10 Novels That Reference the Voice

the voiceTomorrow, December 12, 2015, is the 100th anniversary of the birth of Frank Sinatra, a skinny kid from Hoboken, New Jersey, whose life and career “touched almost every aspect of American culture in the twentieth century,” as his biographer, James Kaplan, puts it. Those who wonder if that claim is merely wild hyperbole need only read Kaplan’s magisterial two-volume life of the iconic singer and actor—Frank: The Voice (volume one) and Sinatra: The Chairman (volume two)—to assuage any doubts.

But that wonderful biography, definitive as it is, represents only the tip of the Sinatra iceberg when it comes to what we have planned for you over the next few days. The Booklist Reader is going to celebrate Ol’ Blue Eyes’ centenary with a whole lot of lists, and we’re starting off with something a little different: Sinatra in fiction. As a gauge of the lingering effect of Sinatra on pop-culture consciousness, we offer these 10 novels, written between 1999 and 2015. In some of them, Sinatra (either a version of the real-life figure or a Sinatra-like character) is the focus of the book; in others, makes only a cameo in someone else’s story; but in all of them, the fact that he’s there means that the cultural zeitgeist has not left Frank behind. So if you’re a Sinatra fan, queue these up on your TBR lists, and if you’re not a fan, sit tight: it will be less than 75 years until the Reader does its Adele centenary celebration.

Detroit Is Our Beat: Tales of the Four Horsemen, by Loren D. Estleman (2015)

Genre veteran Estleman spins an engaging hard-boiled crime tale about four Detroit cops who lead the city’s Racket Squad during WWII. One of their cases involves a death threat against Sinatra, who’s in town for a concert. A fine wartime thriller with a soundtrack from the Voice.

frank in blenderFrank Sinatra in a Blender, by Matthew McBride (2012)

Frank himself does not appear in this insanely dark, grotesquely funny noir novel; rather, the titular Sinatra is a cute little Yorkie whose owner—the boozing, pill-popping, chain-saw-packing Nick Valentine—finds himself in serious dutch with some buffoonish but decidedly lethal crooks who aren’t above depositing Frank the Yorkie in Nick’s blender as a way of stressing how much they want Nick to pay what they see as his debts. The fact that certain real-life hard guys back in the day might not have looked askance at depositing the human Frank Sinatra in an outsize blender only adds a little piquant verisimilitude to this black-on-blacker blend of comedy and noir.

Gilligan’s Wake, by Tom Carson (2003)

Imagine the seven characters from Gilligan’s Island cavorting through the twentieth century and, Zelig-like, interacting with the big names of the day. Take, for example, the Professor affecting foreign policy for years to come by forging FDR’s handwriting in Harry Truman’s copy of How to Win Friends and Influence People. Or, more to our point, Ginger frolicking with both Sinatra and Sammy Davis. Carson’s wacky novel bends 75 years or so of political and television history into a technicolor pastiche as thick with satire as pop-culture references.

maf the dogThe Life and Opinions of Maf the Dog and of His Friend Marilyn Monroe, by Andrew O’Hagan (2010)

A theme is emerging here: if you are writing a wacky, absurdist novel about pop culture, you will, perhaps without even intending to, include something about Frank Sinatra in your book. As in Gilligan’s Wake, Ol’ Blue Eyes turns up in this equally offbeat tale about Marilyn Monroe, as narrated by MM’s dog, Mafia Honey, or “Maf,” for short. Maf is, naturally, versed in the classics, and as he and his owner spend time with such notables as Natalie Wood, Frank Sinatra, and JFK, he offers erudite commentary, sometimes in dialogue with other dogs, on such subjects as interior decorating, celebrity, authenticity, religion, and death. A book like this simply couldn’t have been written without an appearance by Frank.

Make Believe, by Ed Ifkovic (2012)

Ifkovic’s historical mystery series stars a most unlikely real-life character turned sleuth: writer Edna Ferber. In this episode, set in the early 1950s, Edna is in Hollywood to oversee the filming of her novel Show Boat, starring Ava Gardner. The Frank-Ava romance is in full flower at this time, so naturally Ifkovic makes room for both stars in a story that is ostensibly about the murder of a blacklisted screenwriter. But when Ava and Frank make an appearance, all heads turn in their direction.

narrows gateNarrows Gate, by Jim Fusilli (2011)

This tragically too-little-known novel by the rock and pop music critic for the Wall Street Journal is set in Narrows Gate, New Jersey (read Hoboken), in the years before and after World War II. An old-school historical epic, it stars three neighborhood friends whose lives go in wildly divergent directions. One of those friends, Billy “Bebe” Marsala, is a mama’s boy with a velvet voice who goes on to become a heart-throb crooner. Though the obvious connection to Sinatra isn’t acknowledged, Bebe’s life and career follow Sinatra’s closely, except for the shocking ending, which, though based on a real-life incident, takes a sudden and decisive fictional turn. This is a great buddy book and a terrific Mob novel, with shades of Puzo, of course, but above all, it’s must reading for Sinatra devotees.

Painted Horses, by Malcolm Brooks (2012)

The cameo in this moving story of an archaeologist, Catherine LeMay, in the 1950s comes not from Sinatra himself but from one of his albums. Most of the book takes place in New Mexico, but it opens with the young LeMay traveling to England to serve as an intern on a dig. Hoping for adventures both professional and romantic, she carries with her Sinatra’s classic Capitol album Songs for Swingin’ Lovers. Think about that. Like flower children packing their copies on Siddhartha on trips to India, the ‘50s adventurer carries Sinatra, as inspiration or to have handy just in case, if the mood is right. Nothing happens in London, by the way, but later in the novel, the heroine has an on-again, off-again romance that evokes some Ava-Frank-caliber passion.

sinatralandSinatraland, by Sam Kashner (1999)

Remember King of Comedy, the Scorsese film in which wannabe stand-up comic Rupert Pupkin (played by Robert De Niro) is so obsessed with appearing on the Tonight Show that he kidnaps the Carson-like host (played by Jerry Lewis) and stages the program in his basement? Excruciating and at the same time hysterical—just like this brilliant epistolary novel in which a nondescript window-shade salesman in Hoboken, Finkie Finkelstein, is equally obsessed with Frank Sinatra and writes his idol letters stretching over decades, commenting on various triumphs in Frank’s career and contrasting them with his own failings. Yes, it’s a sad, pathetic commentary on celebrity culture, but it’s also so funny it hurts, as the hapless Finkie continues in his determined attempt to mimic Frank (Finkie’s daughter is burdened with the name Nancy Ava). This just could be the best epistolary novel since Ring Lardner’s You Know Me Al.

Spy in a Little Black Dress, by Maxine Kenneth (2012)

The premise sounds silly—Jacqueline Bouvier as a CIA agent in the early ‘50s—but this light, breezy tale (the second in the series) is actually good fun for those willing to suspend a healthy chunk of credulity. Here Jackie, on assignment in Cuba in 1952, meets Fidel Castro (advising him to grow a beard to look older) and is rescued by Ernest Hemingway. Along the way, Sinatra makes an appearance, and Jackie advises him to try for a certain role in From Here to Eternity. The latter bit doesn’t jibe with historical accounts of how Frank landed the coveted part of Maggio, but it’s a tantalizing notion, especially in light of the fact that later, after she became First Lady, Jackie was no fan of Frank and his influence on her husband.

rat pack seriesYou’re Nobody ‘til Somebody Kills You, by Robert J. Randisi (2009)

Randisi’s Rat Pack series takes us back to the Vegas glory years of Frank, Dino, Sammy, et al. Naturally, the fun-loving boys get in trouble from time to time, and when that happens, they need a little help from a friend who knows his way around town. That friend, as Randisi tells it, is Eddie Gianelli, pit boss at the Sands and the go-to guy for Rat Packers in pickles. This time it’s Dean who enlists Eddie’s aid, but the star with a problem is Marilyn Monroe, who thinks she’s being followed, and a nervous MM is likely to grab the pill bottle a little too frequently. There’s also a nice subplot about Frank’s teenager-like pique when his dream BFF, JFK, won’t come over to play (and goes to Bing’s house instead!). Randisi’s light touch and sense of nice-‘n’-easy swing keeps the plot moving in sprightly four-four time. Read this series in the company of a brown-colored beverage and just a cube or two of ice.





About the Author:

After more than 30 years at Booklist, editor and publisher Bill Ott continues to edit the crime fiction section of the magazine and still delights in discovering new hard-boiled writers. Follow him on Twitter at @Booklist_Bill.

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