Jack Kerouac reading from " On The Road"


Music was the food that fueled Jack Kerouac’s soul, drove his writing and brought him his rare moments of solace. What would a mix tape by Jack Kerouac consist of? By combing his letters, journals and published writings, we have designed a fairly good guess for PKM’s readers (and hearers). We are celebrating the centennial of Jack Kerouac’s birth (March 12) with a week of postings about his life and work. Give these tunes a spin while you read on…

Music was an important—no, vital—part of Jack Kerouac’s life and literature. Indeed, the flow of his sentences was shaped by his love of jazz improvisation, and among the first pieces he ever published were his music columns for the Horace Mann Record, at the prep academy then affiliated with Columbia University where he spent his senior year of high school. Getting out of Lowell, the textile mill town where he was raised, and into New York City at age 17 changed the entire fabric of his life, introducing him to the jazz that was playing all over Harlem in 1939-40 when he arrived.

Jack Kerouac, photo from the writers personal collection

Kerouac was a fairly decent singer, too, or a mimic of jazz singing, as can be hear on a number of recordings of Kerouac reading his prose and poetry and, occasionally, breaking out in song.

Just plumbing his own novels and letters and poems, one could pull together a really fine song-list, maybe call it “Jack Kerouac’s Magical Jukebox.”

Jack Kerouac, photo from the writers personal collection

In On the Road alone, he describes one scene of George Shearing playing jazz piano and another of Slim Gaillard working a crowd (including Jack and Neal) into a frenzy during a performance of “Cement Mixer”. Kerouac was said to have written the final draft of On the Road in 3 weeks on Benzedrine while listening to Max Roach albums.

The following are some of the songs and music that would appear on Jack’s Magical Jukebox

“Deep Purple”-Glenn Miller Orchestra

When he was in high school, Kerouac listened to and loved Miller’s popular “serenades,” “Moonlight Serenade” and “Sunrise Serenade.” But his favorite, according to biographer Gerald Nicosia, was “Deep Purple.” Hearing this tune at the Rex Ballroom in Lowell inspired him to learn to dance so that he wouldn’t have to stand at the back while the band played, like a wall flower. He was, by then, a well-known football star at Lowell High School, awkward and strong, and he danced like a jock. Here’s a version of “Deep Purple” recorded by Miller and his orchestra in 1939, around the time Kerouac would have heard it. Vocal by Ray Eberle.

“I Cover the Waterfront”-Billie Holiday.

When Jack was courting Edie Parker, the couple would often go hear her perform in clubs on 52nd Street in New York or up in Harlem, where, according to biographer Gerald Nicosia, “Lady Day would sit at the tables with customers, and Jack and Edie often talked with her.” This was their favorite of Billie Holiday’s songs. This version of “I Cover the Waterfront” was recorded in 1944, around the time Kerouac and Edie Parker were combing the Harlem clubs.

“On the Sunny Side of the Street”-Lester Young [This version was recorded live in Chicago in 1946].

“Donna Lee”-Charlie Parker

When Parker returned to New York in the Fall of 1947, he was drug-free after a stay at Camarillo State Hospital. He was at the peak of his powers then, further cementing the reputation that had one of New York’s premier clubs, Birdland, named after him, and setting up shop at The Royal Roost on Broadway where Symphony Sid Torin broadcast his live performances on his all-night radio show, which Kerouac listened to religiously. This track was cut during this amazing period when Parker was at the top of his game and Kerouac was catching him regularly in the New York clubs. The band is beyond great: CP, Miles Davis-trumpet, Bud Powell-piano; Tommy Potter-bass; Max Roach-drums.

“Charlie Parker”-Poem read by Jack Kerouac

From the album called Poetry for the Beat Generation, which Kerouac recorded with Steve Allen on piano accompaniment.

“I Didn’t Know What Time It Was”-George Shearing

In the first bloom of their brother-like friendship, Kerouac and Neal Cassady explored the city on their own. He describes one time, thinly fictionalized in On the Road as having been witnessed by Sal and Dean, when they went to hear George Shearing, the blind British jazz pianist, play at Birdland. Kerouac describes how the distinguished pianist “with the stiff white collar” and “a delicate English-summer’s-night air about him” was transformed into beat bopping “ecstatic” maniac by their egging him on. “He brought his hair back, his combed hair dissolved,” Kerouac wrote. “He began to sweat”. Dean shouted, “There he is! That’s him! Old God! Old God Shearing!” And when Shearing left the stage, Dean pointed to his vacated piano bench. “God’s empty chair,” he said. This version was released in 1949

“Cement Mixer (Puti Puti)”-Slim Gaillard

Gaillard started out as part of a duo called Slim and Slam that had hits in the 1940s like “Flat Foot Floogie (with a Floy Floy)” and “The Groove Juice Special (Opera in Vout)”. He combined an ability to scat and improvise and operated on the fringes of pre-rock ‘n’ roll R&B and jazz. Jack immortalized Slim in On the Road, creating one of the novel’s greatest set pieces by describing a Gaillard performance that Sal and Dean attended. Dean insisted to Sal that Slim “knows time” and that he is “God.” After the set, Dean buys Slim a drink and then sits across from him, tongue-tied and awestruck. “Every time Slim said ‘Orooni’, Dean said, ‘Yes!’ I sat there with these two madmen. Nothing happened. To Slim Gaillard the whole worl was just one big orooni.” This was the original recording of “Cement Mixer”, released in 1946, around the time Kerouac and Cassady saw him at the gig described in On the Road. Gaillard recorded this many times over the years.

“The Naz”-Lord Buckley

According to David Amram, who was friends with both Kerouac and Lord Buckley, Jack could “quote the comic’s routines from memory.” He was particularly smitten with Buckley’s retelling of the life of Jesus of Nazareth in his routine known as “The Naz.” Recorded live at the Ivar Theatre in Hollywood.

“Why Try to Change Me Now?”-Frank Sinatra

As a teenager, he they young Sinatra was his popular musical idol, and when he left home to attend Columbia University he briefly joined a frat (Phi Gamma Delta) where, according to Nicosia, “with tears in his eyes he would drink beer and listen to Frank Sinatra records full blast.” That early love of Sinatra carried over to the late 1950s when he was involved with Helen Weaver. He found he could win her over, after an argument, by singing Sinatra songs to her. This one was his favorite. This version was recorded and released in 1952, the version Kerouac would most likely to have heard, and preferred.

“Yesterdays,”-Lenny Tristano-

In a letter to Allen Ginsberg in Jan. 1948, Kerouac describes a New Year’s Eve party in New York where the revelers recorded themselves making “mad jazz records…During the course of the night I discovered a new mode of singing that is greater than Sarah Vaughan…This mode of singing combines Lenny Tristano with Vaughan.” He describes going to see Tristano, a blind jazz pianist, and overhearing a group of hipsters proclaiming him “more profound than Stravinsky.” Kerouac calls that “a gross understatement…He is very close to Beethoven, as all the musicians agree. On opening night Tristano’s audience included us, and Leonard Feather the Esquire critic, and Pet Ruggolo, [Stan] Kenton’s arranger, and Neil Hefti and dozens of other great musicians. The guy is standing the music world on its ear.” This version of “Yesterdays” was recorded in 1949.

Ramblin’ Jack Elliott-“Hobo’s Lullaby”

He met another guy named Jack at Helen Parker’s house. This Jack (Ramblin’ Jack Elliott) was sporting a cowboy hat and carrying a beat up guitar. When Kerouac told Elliott, “I like the language of bums,” the folksinger pulled out his guitar and sang a bunch of Woody Guthrie songs, including this one. Kerouac was suitably impressed enough to spend several hours over the course of three days reading the entirety of On The Road’s manuscript to Elliott.

Jack Kerouac tuning in some favorite songs