“Jack’s ultimate vision of success was himself and Sinatra as drinking buddies singing songs to each other.” [ i]

Jack Kerouac loved Frank Sinatra. The smooth, free-wheeling Frankie, ah, what is it about Frank? The cool, the voice, the ring-a-ding-ding. The swing, the sway, the broads, the babes. The tough guy, the mob, the cigarette, the Jack . . . Daniels. When Frank stayed at the swanky Waldorf Astoria in New York, he always ordered a bottle of Jack, a salami, and loaf of Italian bread. All that and to be backed by the great Basie band, Sinatra: “Put on your Basie boots. . . .” Jack [singing along]: “Put on your happy boots!” [ii] Frank’s music swing-a-ling-lings as Jack’s writing swings the way of giggling-ping.
So what did Frank and Jack have in common: devoted mothers, Catholicism, music, drink, dames, big talent, bad reputations, blue eyes, and plenty of misunderstanding from the general public and press, and that included fist fights and a broken head, cracked ribs, and smashed photographers’ cameras.
Frank grew up in Hoboken, New Jersey, a rough, redbrick port city—waterfront, warehouses, and piers—opposite New York City, with tremendous maritime traffic and the rough and tumble that goes with it, the son of Italian immigrant parents with a tough-guy mother. (Frank shoulda nailed the “I coulda been” Terry Malone role in On the Waterfront. Frank was born for the role, a natural, home-grown choice. And, yes, Jack, Marlon shoulda played Dean; [have a look at the 1957 letter Jack wrote to Marlon asking him to buy the rights to On the Road and make it a film] that would have been terrific, or why not just have Neal play Dean?) Jack grew up in Lowell, Massachusetts, a redbrick Merrimack River city in a Franco-American family with a tough guy, businessman, gambling father. Frank’s pop was a boxer and fireman. Dolly Sinatra, Frank’s mama worked as a midwife, abortionist, and local political operator. Gabrielle Kerouac worked in shoe factories. Both mothers sang to their sons.
Francis Albert and Jean Louis were sensitive boys and short, Frank stood 5’7” and Jack 5’8.” Both had many wives, including the luscious, foul-mouthed Ava Gardner, an “Embraceable You” dream girl—Frank one more than Jack, so what Frank lost in height he made up for in an extra wife; Frank four, Jack three, but who’s counting?
After a short stint, Frank left high school without graduating; he wanted to sing. Jack left Columbia University without graduating; he wanted to write. The mothers backed up the sons.
Frank sat at a desk as a sports reporter for a very, very short time, until the editor threw him out. Frank was in no way qualified for that position, but his mother muscled him in there. Jack worked as a sports reporter for a short time at the Lowell Sun, but he blew it, and Jack’s dad was furious and convinced his son would end up a bum. Jack seemed to confirm that when he landed in jail for accessory to murder, and his pop refused to post bail.
Frank was the “boy singer” with Tommy Dorsey; Jack had a girlfriend who sang with Dorsey. Frank and Jack both listened to Bing “Crooner” Crosby.
“Jack and his friends tried to sing like Sinatra and act like Italian gangsters,“ [iii] but did Sinatra’s friends and mob Pal Joeys try to write like Jack? Jack dreamed of becoming a jazz musician and Frank’s best friend [iv] and riding in chauffeured limos protected by bodyguards. [v] At parties, Jack would sing in a drunken, sad voice [vi] causing a lover to remark that from the ache she gleaned in his voice, perhaps they loved Frank more than each other. [vii]
These words from “I Concentrate on You” almost echo one of Jack’s favorite Shakespearean quotes, “What freezings have I felt, what dark days seen.” Set to Jobim’s magic, it proves irresistible.
Whenever skies look gray to me
and trouble begins to brew
Whenever the winter winds become too strong
I concentrate on you
Cold, gray skies, winter winds, and trouble, what more could a romantic Lowell boy want?
The Chairman of the Board was buried with a flask of Jack Daniels and fans of the King of the Beats pour wine on his grave. One more for the road, Frank, baby, and on the road, Jack, flash. Yes, they could have worked out some road songs together, something New York. [viii]
i Nicosia, Gerald. Memory Babe. (Berkeley: University of California Press, 1994), p. 566.
ii ibid., p. 693.
iii ibid., p. 209.
iv ibid., p. 354.
v ibid., p. 653.
vi ibid., p. 580.
vii ibid., p. 608.
viii Kerouac, Jack. Desolation Angels. (New York: Coward-McCann, 1965), p. 142.