Bob Dylan emerged from the smoky Greenwich Village clubs of the early 1960s to help revive American folk music, and then became a spokesman for a generation. Dylan’s songs such as “Blowin’ in the Wind” and “The Times They Are a-Changin” became civil rights and antiwar totems, and he has continued to evolve, sometimes confounding the critics with his changes of direction, for the balance of his six-decade career.
We tend to think of Dylan as primarily an album-oriented artist; 37 of the 39 studio albums he’s made since 1962 have appeared in the Billboard 200. However, the Minnesota native has had 23 songs chart in the Billboard Hot 100, four of which cracked the top 10. The first of these was the generation-defining “Like A Rolling Stone,” which reached No. 2 on the Billboard Hot 100 in 1965. Equaling that chart success was “Rainy Day Women #12 & 35” one year later. In total, Dylan has sold more than 125 million records worldwide. (These are Bob Dylan’s best albums, according to Billboard.)
To determine Bob Dylan’s biggest hits, 24/7 Tempo reviewed performance data on the Billboard Hot 100 charts. Songs were ranked based on an inverse score wherein a week at No. 1 is worth 100 points, a week at No. 2 worth 99 points, and so on, up to a week at No. 100 worth one point. Chart data is current through the week of Oct. 15, 2022.
The accolades have been many in Dylan’s storied career. He’s won 10 Grammy Awards, the Academy Award in 2000 for Best Original Song (“Things Have Changed” from the movie “Wonder Boys”), a special citation Pulitzer Prize in 2008, the Nobel Prize in literature in 2016, and the Presidential Medal of Freedom.
Dylan may be a counterculture icon, but that hasn’t stopped him from making money. Earlier this year, Sony Music Entertainment announced it had bought his entire recorded music catalog, including 39 studio albums and 16 bootlegs. The deal is estimated to have been worth as much as $200 million. The sale followed an agreement in 2020 in which Dylan sold his songwriting catalog to Universal Music Publishing Group for a reported $300 million, among the highest prices ever paid for a musician or group’s songwriting rights. (Here’s a list of the 25 most valuable song catalogs.)
Click here to see Bob Dylan’s all-time biggest hits
23. I Threw It All Away
> Entered Hot 100: May 17, 1969
> Peak position on Hot 100: #85 (for 1 week)
> Total weeks on Hot 100: 5
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22. Leopard-Skin Pill-Box Hat
> Entered Hot 100: May 20, 1967
> Peak position on Hot 100: #81 (for 2 weeks)
> Total weeks on Hot 100: 4
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21. Most Likely You Go Your Way (And I’ll Go Mine) (with The Band)
> Entered Hot 100: Aug. 10, 1974
> Peak position on Hot 100: #66 (for 1 week)
> Total weeks on Hot 100: 5
20. Can You Please Crawl Out Your Window?
> Entered Hot 100: Jan. 1, 1966
> Peak position on Hot 100: #58 (for 1 week)
> Total weeks on Hot 100: 6
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19. Mozambique
> Entered Hot 100: March 13, 1976
> Peak position on Hot 100: #54 (for 1 week)
> Total weeks on Hot 100: 5
18. Sweetheart Like You
> Entered Hot 100: Dec. 17, 1983
> Peak position on Hot 100: #55 (for 1 week)
> Total weeks on Hot 100: 9
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17. A Fool Such As I
> Entered Hot 100: Dec. 15, 1973
> Peak position on Hot 100: #55 (for 2 weeks)
> Total weeks on Hot 100: 7
16. Tonight I’ll Be Staying Here With You
> Entered Hot 100: Nov. 1, 1969
> Peak position on Hot 100: #50 (for 1 week)
> Total weeks on Hot 100: 7
15. On a Night Like This
> Entered Hot 100: Feb. 23, 1974
> Peak position on Hot 100: #44 (for 1 week)
> Total weeks on Hot 100: 6
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14. Just Like a Woman
> Entered Hot 100: Sept. 10, 1966
> Peak position on Hot 100: #33 (for 1 week)
> Total weeks on Hot 100: 6
13. Wigwam
> Entered Hot 100: July 25, 1970
> Peak position on Hot 100: #41 (for 2 weeks)
> Total weeks on Hot 100: 7
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12. Subterranean Homesick Blues
> Entered Hot 100: April 3, 1965
> Peak position on Hot 100: #39 (for 1 week)
> Total weeks on Hot 100: 8
11. Tangled Up in Blue
> Entered Hot 100: March 8, 1975
> Peak position on Hot 100: #31 (for 2 weeks)
> Total weeks on Hot 100: 7
10. Watching the River Flow
> Entered Hot 100: June 26, 1971
> Peak position on Hot 100: #41 (for 1 week)
> Total weeks on Hot 100: 8
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9. George Jackson
> Entered Hot 100: Dec. 4, 1971
> Peak position on Hot 100: #33 (for 1 week)
> Total weeks on Hot 100: 8
8. I Want You
> Entered Hot 100: July 2, 1966
> Peak position on Hot 100: #20 (for 2 weeks)
> Total weeks on Hot 100: 7
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7. Hurricane (Part 1)
> Entered Hot 100: Nov. 29, 1975
> Peak position on Hot 100: #33 (for 2 weeks)
> Total weeks on Hot 100: 11
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6. Gotta Serve Somebody
> Entered Hot 100: Sept. 8, 1979
> Peak position on Hot 100: #24 (for 2 weeks)
> Total weeks on Hot 100: 12
5. Positively 4th Street
> Entered Hot 100: Oct. 2, 1965
> Peak position on Hot 100: #7 (for 1 week)
> Total weeks on Hot 100: 9
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4. Rainy Day Women #12 & 35
> Entered Hot 100: April 16, 1966
> Peak position on Hot 100: #2 (for 1 week)
> Total weeks on Hot 100: 10
3. Like a Rolling Stone
> Entered Hot 100: July 24, 1965
> Peak position on Hot 100: #2 (for 2 weeks)
> Total weeks on Hot 100: 12
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2. Lay Lady Lay
> Entered Hot 100: July 12, 1969
> Peak position on Hot 100: #7 (for 2 weeks)
> Total weeks on Hot 100: 14
1. Knockin’ on Heaven’s Door
> Entered Hot 100: Sept. 1, 1973
> Peak position on Hot 100: #12 (for 2 weeks)
> Total weeks on Hot 100: 16
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