These days, you can take full university classes on Bob Dylan.
“This course examines Bob Dylan the creative genius and enduring and continuing musical, literary, and general cultural phenomenon, in the context of popular and higher literary culture of the last 60 years,” the syllabus for a 2025 class at Harvard reads. “Traces the evolution of his songs and lyrics from their early folk, blues, rock, gospel, and protest roots, through the transition from acoustic to electric, in studio and performative contexts, also through the many persona evolutions and reinventions that have characterized and continue to characterize his career in songwriting, performance, literature, film and painting. Lectures, listening to, viewing, and discussing a broad representation of Dylan’s output.”
But you don’t need to go to an Ivy League school to know a lot about Dylan. Below, we’ve collected 50 questions involving the songwriter pulled right from the archives of Jeopardy! They start out on the easier side and progressively get more challenging from there. How many can you correctly answer?
1. THE ROLE OF A LIFETIME for $200: Timothee Chalamet transformed himself into Bob Dylan for this film and received an Oscar nomination.
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ANSWER: A Complete Unknown
2. CANADA ROCKS for $200: Toronto-born Robbie Robertson was part of the Bob Dylan backup group that made it big on their own using this name.
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ANSWER: The Band
3. THINK TWICE for $200: Bob Dylan wrote “Don’t Think Twice, It’s All Right,” but this “Puff (The Magic Dragon)” trio made it a top 10 hit.
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ANSWER: Peter, Paul & Mary
4. MUSICAL INSTRUMENTS for $200: Bob Dylan often plays one of these, also called a mouth organ.
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ANSWER: Harmonica
5. BOB DYLAN CHRONICLES for $200: “In the jingle jangle morning I’ll come followin’ you.“
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ANSWER: “Mr. Tambourine Man”
Listen to Bob Dylan’s ‘Mr. Tambourine Man’
6. IN A FESTIVAL MOOD for $200: In July 1965 Bob Dylan was booed at the Newport Festival of this, for abandoning that type of music.
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ANSWER: Folk music
7. BOB DYLAN for $200: In 1998 a man with “Soy Bomb” marked on his chest interrupted Bob’s performance at this awards show.
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ANSWER: The Grammys
8. BOB DYLAN SONGS for $200: Bob sang “Knockin’ on Heaven’s Door” on the movie soundtrack “Pat Garrett and” this outlaw.
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ANSWER: Billy the Kid
9. STARTS WITH “Z” for $200: Bob Dylan before he became Dylan.
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ANSWER: Zimmerman
10. GONE WITH THE WINDS for $200: According to Bob Dylan, it’s what’s “Blowin’ in the Wind.”
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ANSWER: The answer
READ MORE: Bob Dylan ‘Bootleg Series’ Albums Ranked Worst to Best
11. THE SINGING “B” for $400: They flew to the top of the charts in 1965 with a cover of Bob Dylan’s “Mr. Tambourine Man.”
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ANSWER: The Byrds
12. THE COLLEGE’S ALUMNI for $400: Bob Dylan, Jessica Lange, Hubert Humphrey.
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ANSWER: The University of Minnesota
13. DYLAN for $400: Born Robert Allen Zimmerman, Bob took his stage name from this man born in Swansea, Wales in 1914.
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ANSWER: Dylan Thomas
14. I’VE TRAVELED EACH & EVERY HIGHWAY for $400: This highway that Bob Dylan “revisited” begins in Thunder Bay, Ontario.
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ANSWER: Highway 61
15. SAY WHAT, BOB? for $400: In Bob Dylan’s “It’s Alright, Ma,” “The child’s balloon eclipses both the Sun and” this; that’s one big balloon, Bob!
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ANSWER: The moon
Listen to Bob Dylan’s ‘It’s Alright, Ma (I’m Only Bleeding)’
16. BOB DYLAN CHRONICLES for $400: “Come mothers and fathers throughout the land and don’t criticize what you can’t understand.”
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ANSWER: “The Times They Are A-Changin'”
17. ROCK WITH YOU for $400: Jakob Dylan, the son of Bob Dylan, is the frontman for this group.
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ANSWER: The Wallflowers
18. NOT THE STATE CAPITAL for $600: Bob Dylan Way winds 1.8 miles through the downtown of this Minnesota port city, Dylan’s birthplace.
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ANSWER: Duluth
19. GIMME AN “F” for $600: In 1985 Bob Dylan went to Philadelphia for Live Aid and to Champaign, Illinois for the first of these benefits.
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ANSWER: Farm Aid
20. “J.P.” for $600: This leather-clad metal band took its name from a Bob Dylan song.
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ANSWER: Judas Priest
READ MORE: Bob Dylan Album Opening Songs Ranked
21. POP CULTURE ON THE AUCTION BLOCK for $800: How does it feel to have an unidentified bidder snag a handwritten draft of Bob Dylan’s lyrics to this song for $2 million?
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ANSWER: “Like a Rolling Stone”
22. BOB DYLAN LYRICS for $800: “May your heart always be joyful, may your song always be sung, and may you stay” this.
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ANSWER: “Forever Young”
23. SONGS OF THE ’60s for $800: Bob Dylan numbered them 12 and 35.
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ANSWER: “Rainy Day Women”
24. BIRTHPLACES for $800: Famous sons of this Minnesota city where Bob Dylan grew up are Vincent Bugliosi and Roger Maris.
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ANSWER: Hibbing
25. A LONELY WORD for $1000: Meaning grief or sadness, it precedes “Row” in a song by Bob Dylan and “Angels” in a book by Jack Kerouac.
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ANSWER: Desolation
Listen to Bob Dylan’s ‘Desolation Row’
26.”M.G.” for $1000: He’s the graphic design legend who created the Bob Dylan poster seen here.
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ANSWER: Milton Glaser
27. INSPIRED SONGS for $1000: This mobster who was slain in Umberto’s Clam House is the subject of Bob Dylan’s song “Joey.”
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ANSWER: Joe Gallo
28. FOLK SINGERS for $1000: Leitch is the last name of this Scottish-born singer featured in the Bob Dylan documentary Don’t Look Back.
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ANSWER: Donovan
29. 20th CENTURY SONG, 21st CENTURY AD for $1200: This lodging service founded in 2007 built an ad around Bob Dylan’s “Shelter From the Storm.”
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ANSWER: Airbnb
30. A COUNTRY BUT NOT A COUNTRY for $1200: The late Echo Helstrom is thought to have inspired Bob Dylan’s song and jukebox musical title “Girl From” here.
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ANSWER: The North Country
31. DYLAN $1200: Richard Gere, Heath Ledger and Cate Blanchett played incarnations of Bob in this unusual biopic.
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ANSWER: I’m Not There
READ MORE: How Robert Zimmerman Became Bob Dylan
32. LAND OF THE “FREE” for $1600: Moving independently, like Bob Dylan in the title of a 1963 album.
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ANSWER: Freewheeling
33. EXTRAORDINARY RENDITIONS for $1600: Bob Dylan said singing his own “All Along the Watchtower” feels like a tribute to this man who did an amazing cover.
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ANSWER: Jimi Hendrix
34. BOB DYLAN for $1600: City Bob made news by not being in December 10, 2016.
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ANSWER: Stockholm
35. WORKING WITH A BEATLE for $1600: “Handle with Care!” Along with George, this ’80s group featured Jeff Lynne, Roy Orbison, Tom Petty and Bob Dylan.
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ANSWER: The Traveling Wilburys
36. AMERICAN AUTHORS for $2000: She dedicated her short story Where Are You Going, Where Have You Been? to Bob Dylan.
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ANSWER: Joyce Carol Oates
37. PLACES IN SONG for $2000: Bob Dylan: “Stuck Inside of ____ With the ____ Blues Again” (Two different cities, please.)
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ANSWER: Mobile and Memphis
Listen to Bob Dylan’s ‘Stuck Inside of Mobile With the Memphis Blues Again’
38. WRAP MUSIC for $2000: In a Bob Dylan song title, this four-word declaration of finality precedes “Baby Blue.”
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ANSWER: “It’s All Over Now”
39. BOB DYLAN for $2000: Folk artist who sang “Diamonds and Rust” about her fling with Bob.
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ANSWER: Joan Baez
40. “WONDER” LAND for $2000: Bob Dylan won an Oscar for the song “Things Have Changed” from this 2000 film.
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ANSWER: Wonder Boys
Bob Dylan Albums Ranked
Through ups and downs, and more comebacks than just about anyone in rock history, the singer-songwriter’s catalog has something for just about everyone.
Gallery Credit: Michael Gallucci
