The Super-Impossible Brain-Busting Bob Dylan Trivia Quiz

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We killed most of a workday compiling this quiz. Now you can kill most of a workday taking it.

Special thanks to Bob Dylan: The Essential Interviews, YouTube, BobDylan.com and The Bob Dylan Encyclopedia, all indispensable resources for the questions and answers in this quiz!


1. At the University of Minnesota, Dylan lived in which fraternity house?

a) Pi Kappa Alpha

b) Alpha Epsilon Pi

c) Sigma Alpha Mu

d) Delta Chi


2. In a 1965 interview, Dylan claimed to be which of the following?

a) A lion tamer

b) A sword swallower

c) A trapeze artist

d) A clown


3. As a producer, Dylan uses which pseudonym?

a) Jack Frost

b) Johnny Apple

c) Jimmy Cricket

d) Jeremy Piven


4. Dylan once said, “He’s a righteous man, a very philosophic man—he’s not your typical bank robber or mercy slayer.” About whom was he speaking?

a) Rubin “Hurricane” Carter

b) Johnny “Guitar” Watson

c) George “The Animal” Steele

c) Jimmy “Superfly” Snuka


5. Who is A.J. Weberman?

a) Dylan’s childhood rabbi

b) The photographer who snapped the cover photo on Time Out Of Mind

c) An obsessive Dylanologist famous for pawing through Bob’s garbage

d) Dylan’s dentist


6. Greil Marcus famously reviewed Dylan’s Self Portrait album with which of the following questions?

a) Has Dylan gone mad?

b) Can I have a refund?

c) Why, Bob, why?

d) What is this shit?


7. Match these Dylan albums to their year of release: Empire Burlesque, Good As I Been To You, Knocked Out Loaded, Down In The Groove

a) 1985

b) 1986

c) 1988

d) 1992


8. Which 1980s film star appears in the video for Dylan’s “Unbelievable”?

a) Charlie Sheen

b) Molly Ringwald

c) Ally Sheedy

d) Michael J. Fox


9. Which two luminaries fight in Dylan’s “Desolation Row”?

a) Sonny Liston and Muhammad Ali

b) Marlon Brando and James Dean

c) Woody Guthrie and Pete Seeger

d) Ezra Pound and T.S. Eliot


10. To whom does Dylan dedicate the song “High Water” on his Love and Theft album?

a) Charley Patton

b) Robert Johnson

c) Son House

d) Blind Willie McTell


11. How many Dylan song titles start with the letter “V”?

a) 0

b) 1

c) 2

d) 3


12. Bob Dylan collaborated with which hip-hop pioneer on a 1986 song called “Street Rock”?

a) Grandmaster Flash

b) Kurtis Blow

c) Afrika Bambaataa

d) LL Cool J


13. New York Sessions is the title of a famous bootleg featuring alternate takes from which classic album?

a) The Freewheelin’ Bob Dylan

b) Highway 61 Revisited

c) Blonde On Blonde

d) Blood On The Tracks


14) Which vocalist takes his turn immediately after Dylan in “We Are The World”?

a) Ray Charles

b) Stevie Wonder

c) Bruce Springsteen

d) Paul Simon


15) Which Dylan song did Billboard describe as a “slick ditty” and “a sailor’s lament, sung softly and tenderly”?

a) “The Times They Are A-Changin’”

b) “Girl From The North Country”

c) “With God On Our Side”

d) “Blowin’ In The Wind”


16) Dylan’s 2008 release Tell Tale Signs was which volume of his Bootleg Series?

a) 4

b) 8

c) 12

d) 16


17) What is Dylan’s astrological sign?

a) Leo

b) Scorpio

c) Capricorn

d) Gemini


18) Dylan once described his “real message” as, “Keep a good head and always carry a…”?

a) Rabbit’s foot

b) Light bulb

c) Handbag

d) Grudge


19) What was written on the bare chest of the interpretive dancer who crashed Dylan’s 1998 Grammy performance?

a) Soy Bomb

b) Tofu Missile

c) Ginkgo Gun

d) Fiber Buster


20) In the epic story-song “Lily, Rosemary and the Jack of Hearts,” which character owns a diamond mine?

a) Lily

b) Rosemary

c) The Jack of Hearts

d) Big Jim


Answers on the next page!


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