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50 free Jack Kerouac trivia questions with answers — literature quiz, new questions added Aug 2026.
This Jack Kerouac trivia quiz covers the King of the Beats from a French-speaking childhood in Lowell to a Florida hospital in 1969. The easy questions handle his hometown, the friends who founded the Beat Generation with him, the roll of paper he fed into his typewriter, and the man behind Dean Moriarty. From there it moves into the books: who is who in On the Road, the poet fictionalised as Japhy Ryder, the fire lookout summer, the cabin at Big Sur and the ten days it took to write about it. The harder end is for people who own more than one Kerouac paperback: the football injury at Columbia, the eight-day Navy career, the murder that got him arrested, the critic whose review made him famous, the Colts owner who bought the scroll, the Zen teachers whose criticism stung, and the keyboardist who said his band owed its existence to On the Road. Every answer was checked against encyclopaedia entries on Kerouac, his novels, Neal Cassady and the Beat Generation, and the supporting sentence is stored with each question. If you enjoy this one, our Beat Generation, American literature and 1950s quizzes are natural next stops.
30 of 50 questions with answers and explanations. Play the quiz
Q 01In which Massachusetts mill town was Jack Kerouac born in 1922?
Lowell
He learned English only at six and kept a marked accent into his late teens.
Q 02Kerouac's family spoke which language at home during his childhood?
French
His parents were French-Canadian, and the family called him 'Ti Jean'.
Q 03Which two writers are named alongside Kerouac as pioneers of the Beat Generation?
William S. Burroughs and Allen Ginsberg
The core group, with Lucien Carr and a Times Square hustler, met around Columbia University in 1944.
Q 04Kerouac's older brother Gerard, later the subject of Visions of Gerard, died of what at the age of nine?
Rheumatic fever
Four-year-old Jack later said Gerard followed him through life as a guardian angel.
Q 05Kerouac won a scholarship to Columbia University for his talent in which sport?
Football
He was a high-school running back; Boston College and Notre Dame also made offers.
Q 06What ended Kerouac's promising first season on the Columbia team?
He broke a leg
In his second year he feuded with coach Lou Little, who kept him on the bench, and he eventually dropped out.
Q 07In 1943 Kerouac was discharged from the Navy Reserve after eight days of active duty with what diagnosis?
Schizoid personality
He said he had asked for an aspirin for a headache and been sent to the sick list; the report called his character 'indifferent'.
Q 08Kerouac wrote his first novel, The Sea Is My Brother, while serving as what in 1942?
A Merchant Mariner
He served on the SS Dorchester before its maiden voyage; the ship was later torpedoed. The novel appeared only in 2011.
Q 09In 1944 Kerouac was arrested as a material witness after his friend Lucien Carr killed whom?
David Kammerer
Kerouac disposed of the knife and buried the victim's glasses; he and Burroughs later wrote a novel about it, And the Hippos Were Boiled in Their Tanks.
Q 10Why did Kerouac marry Edie Parker in August 1944, with two detectives as witnesses?
Her parents paid his bail
His own father had refused to pay; the marriage was annulled in 1948.
Q 11Under what first name was Kerouac credited on his first novel, The Town and the City?
John
Editor Robert Giroux cut about 400 pages from the Thomas Wolfe-influenced manuscript, and it sold poorly.
Q 12Kerouac famously typed the first draft of On the Road onto what?
A 120-foot roll of taped-together paper
He cut tracing paper into strips so he would never have to stop to reload the typewriter.
Q 13How long did Kerouac take to type the final scroll draft of On the Road in April 1951?
About three weeks
His wife kept him supplied with benzedrine, cigarettes, pea soup and coffee.
Q 21Who bought the original On the Road scroll at auction in 2001 for $2.43 million?
Jim Irsay
The Indianapolis Colts owner sent it on tour to museums in the US, Ireland and Britain; it sold again in 2026 for $12.1 million.
Q 22Which director bought the film rights to On the Road in 1980 for $95,000?
Francis Ford Coppola
He cycled through several screenwriters and drafted a version with his son Roman before the film was finally made three decades later.
Q 23Who directed the 2012 film of On the Road, which competed for the Palme d'Or at Cannes?
Walter Salles
Coppola chose him after seeing The Motorcycle Diaries; Sam Riley played Sal.
Q 14Which friend, the model for Dean Moriarty, did most of the driving on the trips behind On the Road?
Neal Cassady
Kerouac himself had no driver's licence; he learned to drive at 34 and never got a formal one.
Q 15Under what name does Kerouac appear as the narrator of On the Road?
Sal Paradise
In later books his alter ego is usually called Jack Duluoz; his publishers would not let him reuse the same names.
Q 16Which publisher finally brought out On the Road in 1957 after years of rejection?
Viking Press
Kerouac was in a small house in Orlando, Florida, waiting for its release when the New York Times review made him famous overnight.
Q 17Which New York Times critic's 1957 review proclaimed Kerouac the voice of a new generation?
Gilbert Millstein
Within nine months Kerouac no longer felt safe in public and was beaten up outside the San Remo Cafe in Greenwich Village.
Q 18In On the Road, the character Old Bull Lee, visited in Algiers, Louisiana, is based on which writer?
William S. Burroughs
Ginsberg appears as Carlo Marx, whom Sal meets in Denver.
Q 19The narrator of On the Road leaves his aunt's New Jersey house in July 1947 with how much money?
$50
He hitchhikes and rides buses to Denver, where Dean and Carlo Marx are waiting.
Q 20Where does Sal fall ill with dysentery and get abandoned by Dean near the end of On the Road?
Mexico City
'When I got better I realized what a rat he was,' Sal reflects, before forgiving 'the impossible complexity of his life'.
Q 24Who played Dean Moriarty in the 2012 film of On the Road?
Garrett Hedlund
Sam Riley took the role of the narrator, and Kristen Stewart was among the cast.
Q 25Kerouac credited which Times Square hustler with first using the word 'beat' in conversation with him?
Herbert Huncke
Huncke meant someone broke and without prospects; Kerouac added the senses of 'upbeat' and 'beatific'.
Q 26What did Kerouac insist he was, showing a reporter a papal portrait he had painted?
A Catholic
He showed the reporter a painting of Pope Paul VI and said he had painted it himself.
Q 27Kerouac's The Dharma Bums centres on his friendship with which poet, fictionalised as Japhy Ryder?
Gary Snyder
Snyder introduced Kerouac to Buddhism; the book includes their climb of Matterhorn Peak in California.
Q 28In The Dharma Bums, 'Alvah Goldbook' reads a poem called 'Wail'. What was the real poem?
Howl
Kerouac claims he got things going by collecting coins for three gallon jugs of California Burgundy.
Q 29Kerouac spent summer 1956 as a fire lookout on which mountain in Washington's North Cascades?
Desolation Peak
He found it desperately lonely: 'Many's the time I thought I'd die of boredom or jump off the mountain,' he wrote in Desolation Angels.
Q 30How long did Kerouac take to write The Dharma Bums in Orlando in late 1957?
About 12 days
He typed it between 26 November and 7 December onto a ten-foot length of teleprinter paper.