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50 free Bob Dylan trivia questions with answers — music quiz, new questions added Aug 2026.
39 free Bob Dylan trivia questions with answers. Bob Dylan trivia can go in several directions at once, and this quiz takes most of them. The 50 questions start with the biography — the birth name, the iron-mining town, the trip to a New Jersey hospital to meet Woody Guthrie — and move through the records that changed popular music. There are questions on the songs themselves: where the melody of 'Blowin' in the Wind' came from, why radio refused to play a six-minute single, whose improvised organ part Dylan pushed to the front of the mix, and which album closes with eleven acoustic minutes. Later rounds cover the motorcycle crash, the basement recordings, the gospel years, the Traveling Wilburys and the 2016 Nobel Prize. Every answer was checked against a primary reference before publication, so the chart positions, dates and album details are accurate rather than approximate. Difficulty runs from questions any radio listener will get to a few that require a serious record collection.
30 of 50 questions with answers and explanations. Play the quiz
Q 01What name was Bob Dylan given at birth?
Robert Allen Zimmerman
He was born at St Mary's Hospital in Duluth in May 1941. He took his stage name legally some years later.
Q 02In which northern state was Bob Dylan born?
Minnesota
The town was Duluth, on Lake Superior. The family moved inland when he was six.
Q 03In which iron-mining town did Dylan spend most of his childhood?
Hibbing
The family moved there after his father contracted polio. It was his mother's home town.
Q 04Which musician did Dylan travel to New York to visit in January 1961?
Woody Guthrie
His idol was in a psychiatric hospital in New Jersey by then. Dylan's early style is a direct copy of his.
Q 05From which traditional song did the melody of 'Blowin' in the Wind' partly derive?
No More Auction Block
Pete Seeger identified the source and Dylan later confirmed it. The spiritual is connected to 'We Shall Overcome'.
Q 06In which year did Dylan write 'Blowin' in the Wind'?
1962
It appeared on The Freewheelin' Bob Dylan the following year. A folk trio's cover version made it a hit.
Q 07Whose cover of the same song became a huge hit weeks after Dylan's own version?
Peter, Paul and Mary
They released it three weeks after The Freewheelin' Bob Dylan came out. It spent five weeks at the top of the Middle-Road chart.
Q 08At which 1965 event did Dylan play his first electric set since high school?
The Newport Folk Festival
Mike Bloomfield played guitar and Al Kooper the organ. The reaction split the folk world in two.
Q 09How high did 'Like a Rolling Stone' reach on the US chart in 1965?
Number two
It ran to six minutes and thirteen seconds, which radio stations initially refused to play. Public demand forced them to relent.
Q 10Why did radio stations initially refuse to play 'Like a Rolling Stone'?
It was over six minutes long
Nothing that long had been a pop single before. Listener demand eventually forced it onto air in full.
Q 11What did Dylan insist on when he heard the playback of 'Like a Rolling Stone'?
Turning the organ up in the mix
The producer objected that Al Kooper was not even an organ player. The improvised part is now the most famous thing on the record.
Q 12Where did Rolling Stone magazine place 'Like a Rolling Stone' in its 2004 and 2010 greatest songs lists?
Number one
It topped both editions of the list. The 2021 revision moved it down.
Q 13Which album did Dylan release on 30 August 1965, with rock musicians backing every track?
Highway 61 Revisited
Q 21Which album did Dylan record in September 1974, with songs about ruptured relationships?
Blood on the Tracks
It received mixed reviews on release early the next year. It is now routinely called his best album.
Q 22What did Dylan do in the late 1970s that surprised his audience?
He became a born-again Christian
He took a three-month discipleship course with the Association of Vineyard Churches. Three gospel albums followed.
Q 23Which guitarist played on Slow Train Coming in 1979?
Mark Knopfler
Jerry Wexler produced the album. It won Dylan a Grammy for Best Male Rock Vocal Performance.
It closes with the eleven-minute acoustic exception 'Desolation Row'. Rolling Stone later placed it fourth on its greatest albums list.
Q 14Which track closes that 1965 album as its sole acoustic song?
Desolation Row
It runs to eleven minutes with classical guitar flourishes. Everything else on the record is electric.
Q 15Where did Rolling Stone rank that album in its 2003 500 Greatest Albums list?
Fourth
The magazine called it one of those albums that changed everything; the 2020 revision moved it to 18th. The route it is named after runs past Dylan's birthplace.
Q 16What happened to Dylan on 29 July 1966?
He crashed his motorcycle
It happened near his home in Woodstock, New York, on a Triumph Tiger 100. He withdrew from public life for months afterwards.
Q 17What make of motorcycle was Dylan riding at the time?
A Triumph
The model was a Tiger 100. He said he broke several vertebrae in his neck.
Q 18Roughly how many songs did Dylan record in seclusion during 1967?
Over 100
They were taped at his Woodstock home and in the basement of a house called Big Pink. A selection was finally released in 1975.
Q 19What was the nearby house where those 1967 sessions were taped called?
Big Pink
The Hawks, later known as The Band, lived there. Columbia released a selection as The Basement Tapes.
Q 20In which year did Columbia release The Basement Tapes?
1975
The recordings had circulated as bootlegs for years before that. A full box set followed decades later.
Q 24Which song won Dylan a Grammy for Best Male Rock Vocal Performance?
Gotta Serve Somebody
It opens his first gospel album. Two more Christian records followed in 1980 and 1981.
Q 25Which supergroup did Dylan join in 1988?
The Traveling Wilburys
George Harrison, Jeff Lynne, Roy Orbison and Tom Petty made up the rest. They pretended to be half-brothers.
Q 26What pseudonym did Dylan use in that supergroup?
Lucky Wilbury
Harrison was Nelson, Lynne was Otis, Orbison was Lefty and Petty was Charlie T Junior. The joke was that they were all brothers.
Q 27Which member of the 1988 supergroup died that December?
Roy Orbison
He had a heart attack weeks after the first album came out. The others carried on as a quartet.
Q 28Which Grammy did that supergroup win in 1990?
Best Rock Performance by a Duo or Group
The debut album was both a critical and a commercial success. Five established stars won a group award between them.
Q 29How was Dylan's 2016 Nobel citation worded?
For new poetic expressions in song
The citation praised new poetic expressions within the great American song tradition. He had already received a Pulitzer special citation in 2008.
Q 30What was the wording of Dylan's Nobel citation?
For creating new poetic expressions in song
The committee framed it as work in the great American song tradition. He did not attend the ceremony.