54 Bob Dylan Trivia Questions Every Music True Fan Must Answer!
Bob Dylan, an enigmatic figure whose influence on music and culture spans over half a century, remains a subject of fascination for fans and historians alike. With a career that has constantly evolved, Dylan’s repertoire includes folk anthems, rock classics, and profound ballads that have earned him the Nobel Prize in Literature. His lyrical prowess and musical innovation have secured his status as a legend, making his life and work a treasure trove for trivia enthusiasts.
Diving into the world of Bob Dylan trivia is like embarking on a journey through the annals of modern music history. Each question and answer unveils a layer of the artist’s expansive narrative, from his early days in the Greenwich Village folk scene to his recent ventures. Dylan’s ability to reinvent himself while maintaining his distinctive voice has left a rich legacy ripe for exploration.
As we peel back the layers of Dylan’s storied career, we uncover fascinating tidbits that offer a glimpse into the man behind the music. Whether you’re a longtime admirer or a curious newcomer, these 54 Bob Dylan trivia questions promise to challenge and enlighten, shedding light on the lesser-known aspects of this iconic artist’s life and work.
Round 1 – Multiple Choice Bob Dylan Questions
- What is Bob Dylan’s birth name?
- A) Robert Zimmerman
- B) Bob Smith
- C) Dylan Thomas
- D) Robert Johnson
- In what year was Bob Dylan born?
- A) 1935
- B) 1941
- C) 1950
- D) 1962
- Which album is considered Bob Dylan’s breakthrough work?
- A) Blonde on Blonde
- B) The Freewheelin’ Bob Dylan
- C) Highway 61 Revisited
- D) Blood on the Tracks
- What instrument is Bob Dylan famous for playing?
- A) Guitar
- B) Piano
- C) Harmonica
- D) Drums
- Which song did Dylan famously go electric with at the Newport Folk Festival in 1965?
- A) “Like a Rolling Stone”
- B) “Blowin’ in the Wind”
- C) “Maggie’s Farm”
- D) “The Times They Are A-Changin'”
- In which city was Bob Dylan born?
- A) Duluth, Minnesota
- B) New York, New York
- C) Nashville, Tennessee
- D) Chicago, Illinois
- For which song did Bob Dylan win a Nobel Prize in Literature?
- A) His entire body of work
- B) “Mr. Tambourine Man”
- C) “All Along the Watchtower”
- D) “Knockin’ on Heaven’s Door”
- What genre is Bob Dylan primarily associated with?
- A) Rock
- B) Folk
- C) Blues
- D) Country
- Which Bob Dylan album was the first to feature electric instruments?
- A) Bringing It All Back Home
- B) Another Side of Bob Dylan
- C) John Wesley Harding
- D) Nashville Skyline
- In which year did Bob Dylan win the Nobel Prize in Literature?
- A) 2010
- B) 2012
- C) 2016
- D) 2018
- What is the title of the documentary directed by Martin Scorsese about Bob Dylan?
- A) No Direction Home
- B) The Last Waltz
- C) Rolling Thunder Revue
- D) Shine a Light
- Which Bob Dylan song became an unofficial anthem of the Civil Rights Movement?
- A) “Blowin’ in the Wind”
- B) “Masters of War”
- C) “A Hard Rain’s A-Gonna Fall”
- D) “Forever Young”
- Bob Dylan’s “Blood on the Tracks” album is often interpreted as being about?
- A) His childhood in Minnesota
- B) The Vietnam War
- C) The breakdown of his marriage
- D) His motorcycle accident
- Which artist famously covered Bob Dylan’s “All Along the Watchtower”?
- A) Eric Clapton
- B) Jimi Hendrix
- C) The Beatles
- D) Neil Young

Round 1 – Answers
- What is Bob Dylan’s birth name?
- Answer: A) Robert Zimmerman
- In what year was Bob Dylan born?
- Answer: B) 1941
- Which album is considered Bob Dylan’s breakthrough work?
- Answer: B) The Freewheelin’ Bob Dylan
- What instrument is Bob Dylan famous for playing?
- Answer: A) Guitar
- Which song did Dylan famously go electric with at the Newport Folk Festival in 1965?
- Answer: C) “Maggie’s Farm”
- In which city was Bob Dylan born?
- Answer: A) Duluth, Minnesota
- For which song did Bob Dylan win a Nobel Prize in Literature?
- Answer: A) His entire body of work
- What genre is Bob Dylan primarily associated with?
- Answer: B) Folk
- Which Bob Dylan album was the first to feature electric instruments?
- Answer: A) Bringing It All Back Home
- In which year did Bob Dylan win the Nobel Prize in Literature?
- Answer: C) 2016
- What is the title of the documentary directed by Martin Scorsese about Bob Dylan?
- Answer: A) No Direction Home
- Which Bob Dylan song became an unofficial anthem of the Civil Rights Movement?
- Answer: A) “Blowin’ in the Wind”
- Bob Dylan’s “Blood on the Tracks” album is often interpreted as being about?
- Answer: C) The breakdown of his marriage
- Which artist famously covered Bob Dylan’s “All Along the Watchtower”?
- Answer: B) Jimi Hendrix
Round 2 – Multiple Choice Bob Dylan Questions
- What is the name of the book Bob Dylan published in 1971, a collection of his lyrics and writings?
- A) Chronicles: Volume One
- B) Tarantula
- C) The Lyrics: 1961-2012
- D) Writings and Drawings
- Which book by Bob Dylan provides a unique insight into his life and was published in 2004?
- A) Chronicles: Volume One
- B) The Times They Are a-Changin’
- C) Bob Dylan: A Retrospective
- D) The Essential Interviews
- Which iconic artist did NOT cover a Bob Dylan song?
- A) Adele
- B) Johnny Cash
- C) Beyoncé
- D) Jimi Hendrix
- Bob Dylan has been awarded all of the following except?
- A) A Pulitzer Prize
- B) A Nobel Prize in Literature
- C) An Academy Award
- D) A Grammy Lifetime Achievement Award
- Which Bob Dylan album marked his return to traditional folk music in the 1990s?
- A) Time Out of Mind
- B) Oh Mercy
- C) World Gone Wrong
- D) Love and Theft
- Bob Dylan’s “The Times They Are A-Changin'” was released in what year?
- A) 1961
- B) 1963
- C) 1964
- D) 1965
- Which Bob Dylan song was inspired by the Italian film “La Strada”?
- A) “Mr. Tambourine Man”
- B) “A Hard Rain’s A-Gonna Fall”
- C) “I Want You”
- D) “When The Ship Comes In”
- Which city is closely associated with the early career of Bob Dylan, where he was known to perform in coffee houses and folk clubs?
- A) Chicago, Illinois
- B) San Francisco, California
- C) New York City, New York
- D) Austin, Texas
- In 2009, Bob Dylan released an album of Christmas music. What is the title of this album?
- A) Christmas in the Heart
- B) A Very Dylan Christmas
- C) Holiday Blues
- D) Winterlude
- Bob Dylan has used many pseudonyms over the years. Which of the following is NOT one of them?
- A) Jack Frost
- B) Blind Boy Grunt
- C) Elston Gunn
- D) Johnny Rhythm
- Bob Dylan was a member of which supergroup alongside George Harrison, Roy Orbison, Jeff Lynne, and Tom Petty?
- A) The Traveling Wilburys
- B) The Highwaymen
- C) The Band
- D) Crosby, Stills, Nash & Young

Round 2 – Answers
- What is the name of the book Bob Dylan published in 1971, a collection of his lyrics and writings?
- Answer: B) Tarantula
- Which book by Bob Dylan provides a unique insight into his life and was published in 2004?
- Answer: A) Chronicles: Volume One
- Which iconic artist did NOT cover a Bob Dylan song?
- Answer: C) Beyoncé
- Bob Dylan has been awarded all of the following except?
- Answer: A) A Pulitzer Prize
- Which Bob Dylan album marked his return to traditional folk music in the 1990s?
- Answer: C) World Gone Wrong
- Bob Dylan’s “The Times They Are A-Changin'” was released in what year?
- Answer: C) 1964
- Which Bob Dylan song was inspired by the Italian film “La Strada”?
- Answer: A) “Mr. Tambourine Man”
- Which city is closely associated with the early career of Bob Dylan, where he was known to perform in coffee houses and folk clubs?
- Answer: C) New York City, New York
- In 2009, Bob Dylan released an album of Christmas music. What is the title of this album?
- Answer: A) Christmas in the Heart
- Bob Dylan has used many pseudonyms over the years. Which of the following is NOT one of them?
- Answer: D) Johnny Rhythm
- Bob Dylan was a member of which supergroup alongside George Harrison, Roy Orbison, Jeff Lynne, and Tom Petty?
- Answer: A) The Traveling Wilburys
Round 3 – Multiple Choice Bob Dylan Questions
- Which artist has NOT been cited as a major influence on Bob Dylan’s music?
- A) Woody Guthrie
- B) Robert Johnson
- C) Hank Williams
- D) Mozart
- In which film did Bob Dylan play the character Alias?
- A) Pat Garrett & Billy the Kid
- B) Masked and Anonymous
- C) Renaldo and Clara
- D) Hearts of Fire
- What is the title of Bob Dylan’s first published book of art, which includes a collection of his drawings and sketches?
- A) The Drawn Blank Series
- B) Chronicles: Volume One
- C) Mondo Scripto
- D) The Beaten Path
- Which historical figure is NOT mentioned in Bob Dylan’s song “Desolation Row”?
- A) Albert Einstein
- B) Cinderella
- C) William Shakespeare
- D) Julius Caesar
- Bob Dylan’s “Never Ending Tour” began in which year?
- A) 1988
- B) 1990
- C) 1986
- D) 1992
- Which song did Bob Dylan write as a tribute to boxer Davey Moore?
- A) “Who Killed Davey Moore?”
- B) “Hurricane”
- C) “Only a Pawn in Their Game”
- D) “The Lonesome Death of Hattie Carroll”
- What significant event in Bob Dylan’s life occurred in July 1966?
- A) His first album release
- B) His motorcycle accident near Woodstock, NY
- C) Winning his first Grammy Award
- D) His conversion to Christianity
- Which Bob Dylan song from the album “Highway 61 Revisited” was over 6 minutes long and broke the typical length for a radio single?
- A) “Like a Rolling Stone”
- B) “Tangled Up in Blue”
- C) “Desolation Row”
- D) “All Along the Watchtower”
- Which album did Bob Dylan release after his conversion to Christianity?
- A) Slow Train Coming
- B) Blood on the Tracks
- C) Desire
- D) Street-Legal
- What is the title of the song that Bob Dylan wrote as a tribute to John Lennon?
- A) “Roll On John”
- B) “Forever Young”
- C) “Blowin’ in the Wind”
- D) “Song to Woody”
- Which of these Bob Dylan albums is entirely instrumental?
- A) New Morning
- B) Nashville Skyline
- C) Self Portrait
- D) None, as all his albums contain vocal tracks
- What unique feature does Bob Dylan’s “The Freewheelin’ Bob Dylan” album cover have?
- A) It features Dylan alone without any musical instruments.
- B) Dylan is walking down a snowy New York street with his then-girlfriend Suze Rotolo.
- C) It was shot entirely in black and white.
- D) It features a painting by Dylan.
- Bob Dylan’s album “John Wesley Harding” features which famous song that has been covered by numerous artists?
- A) “All Along the Watchtower”
- B) “I’ll Be Your Baby Tonight”
- C) “The Ballad of Frankie Lee and Judas Priest”
- D) “Drifter’s Escape”
- Bob Dylan’s “Chronicles: Volume One” is part of what literary genre?
- A) Fiction
- B) Autobiography
- C) Poetry
- D) Historical Fiction
- Bob Dylan’s voice has been described as?
- A) Operatic
- B) Gravelly
- C) Soprano
- D) Whispery

Round 3 – Answers
- Which artist has NOT been cited as a major influence on Bob Dylan’s music?
- Answer: D) Mozart
- In which film did Bob Dylan play the character Alias?
- Answer: A) Pat Garrett & Billy the Kid
- What is the title of Bob Dylan’s first published book of art, which includes a collection of his drawings and sketches?
- Answer: A) The Drawn Blank Series
- Which historical figure is NOT mentioned in Bob Dylan’s song “Desolation Row”?
- Answer: D) Julius Caesar
- Bob Dylan’s “Never Ending Tour” began in which year?
- Answer: A) 1988
- Which song did Bob Dylan write as a tribute to boxer Davey Moore?
- Answer: A) “Who Killed Davey Moore?”
- What significant event in Bob Dylan’s life occurred in July 1966?
- Answer: B) His motorcycle accident near Woodstock, NY
- Which Bob Dylan song from the album “Highway 61 Revisited” was over 6 minutes long and broke the typical length for a radio single?
- Answer: A) “Like a Rolling Stone”
- Which album did Bob Dylan release after his conversion to Christianity?
- Answer: A) Slow Train Coming
- What is the title of the song that Bob Dylan wrote as a tribute to John Lennon?
- Answer: A) “Roll On John”
- Which of these Bob Dylan albums is entirely instrumental?
- Answer: D) None, as all his albums contain vocal tracks
- What unique feature does Bob Dylan’s “The Freewheelin’ Bob Dylan” album cover have?
- Answer: B) Dylan is walking down a snowy New York street with his then-girlfriend Suze Rotolo.
- Bob Dylan’s album “John Wesley Harding” features which famous song that has been covered by numerous artists?
- Answer: A) “All Along the Watchtower”
- Bob Dylan’s “Chronicles: Volume One” is part of what literary genre?
- Answer: B) Autobiography
- Bob Dylan’s voice has been described as?
- Answer: B) Gravelly
Round 4 – Multiple Choice Bob Dylan Questions
- What is the name of Bob Dylan’s radio program that debuted in May 2006?
- A) The Dylan Hour
- B) Theme Time Radio Hour
- C) Bob Dylan’s Blues
- D) Highway 61 Revisited Radio
- What controversial electric guitar did Bob Dylan use at the 1965 Newport Folk Festival?
- A) Gibson Les Paul
- B) Fender Stratocaster
- C) Fender Telecaster
- D) Gibson SG
- Which Bob Dylan album contains the song “Visions of Johanna”?
- A) Blonde on Blonde
- B) Highway 61 Revisited
- C) Blood on the Tracks
- D) Desire
- Bob Dylan was awarded the Medal of Freedom in which year?
- A) 2010
- B) 2012
- C) 2014
- D) 2016
- Which song from the album “Nashville Skyline” saw Bob Dylan duetting with Johnny Cash?
- A) “Girl from the North Country”
- B) “Lay Lady Lay”
- C) “Country Pie”
- D) “I Threw It All Away”
- Which Bob Dylan song was inspired by his wife, Sara Lownds?
- A) “Sara”
- B) “Lay Lady Lay”
- C) “Sad Eyed Lady of the Lowlands”
- D) “Love Minus Zero/No Limit”
- Bob Dylan’s soundtrack for which film won him an Academy Award?
- A) Pat Garrett & Billy the Kid
- B) Wonder Boys
- C) I’m Not There
- D) The Hurricane
- Which song did Bob Dylan write in response to the assassination of Medgar Evers?
- A) “The Times They Are A-Changin'”
- B) “Only a Pawn in Their Game”
- C) “Blowin’ in the Wind”
- D) “A Hard Rain’s A-Gonna Fall”
- Bob Dylan’s “Modern Times” achieved significant chart success. What is its notable achievement on the Billboard 200?
- A) It was his first double album to reach No. 1.
- B) It was his first album in the 21st century to reach No. 1.
- C) It marked his return to No. 1 after more than 30 years.
- D) It was the highest-selling album of his career.
- Bob Dylan’s artwork has been exhibited in major galleries around the world. What is one medium he commonly uses?
- A) Sculpture
- B) Watercolor
- C) Digital Art
- D) Acrylic Paint
- Which Bob Dylan album is known for its exploration of religious themes following his conversion to Christianity?
- A) “Slow Train Coming”
- B) “Saved”
- C) “Shot of Love”
- D) “Infidels”
- Bob Dylan’s famous “Don’t Look Back” documentary was filmed during which tour?
- A) 1965 UK tour
- B) 1966 European tour
- C) 1974 American tour
- D) 1975 Rolling Thunder Revue
- What is the name of Bob Dylan’s book that combines his lyrics with his own hand-drawn art?
- A) “Chronicles: Volume One”
- B) “Tarantula”
- C) “Mondo Scripto”
- D) “The Lyrics: Since 1962”
- In which year did Bob Dylan release “Rough and Rowdy Ways,” his first album of original songs in eight years?
- A) 2018
- B) 2020
- C) 2022
- D) 2016
Round 4 – Answers
- What is the name of Bob Dylan’s radio program that debuted in May 2006?
- Answer: B) Theme Time Radio Hour
- What controversial electric guitar did Bob Dylan use at the 1965 Newport Folk Festival?
- Answer: B) Fender Stratocaster
- Which Bob Dylan album contains the song “Visions of Johanna”?
- Answer: A) Blonde on Blonde
- Bob Dylan was awarded the Medal of Freedom in which year?
- Answer: B) 2012
- Which song from the album “Nashville Skyline” saw Bob Dylan duetting with Johnny Cash?
- Answer: A) “Girl from the North Country”
- Which Bob Dylan song was inspired by his wife, Sara Lownds?
- Answer: A) “Sara”
- Bob Dylan’s soundtrack for which film won him an Academy Award?
- Answer: B) Wonder Boys
- Which song did Bob Dylan write in response to the assassination of Medgar Evers?
- Answer: B) “Only a Pawn in Their Game”
- Bob Dylan’s “Modern Times” achieved significant chart success. What is its notable achievement on the Billboard 200?
- Answer: C) It marked his return to No. 1 after more than 30 years.
- Bob Dylan’s artwork has been exhibited in major galleries around the world. What is one medium he commonly uses?
- Answer: B) Watercolor
- Which Bob Dylan album is known for its exploration of religious themes following his conversion to Christianity?
- Answer: B) “Saved”
- Bob Dylan’s famous “Don’t Look Back” documentary was filmed during which tour?
- Answer: A) 1965 UK tour
- What is the name of Bob Dylan’s book that combines his lyrics with his own hand-drawn art?
- Answer: C) “Mondo Scripto”
- In which year did Bob Dylan release “Rough and Rowdy Ways,” his first album of original songs in eight years?
- Answer: B) 2020