"Key West (Philosopher Pirate)"
Song by Bob Dylan
from the album Rough and Rowdy Ways
ReleasedJune 19, 2020
RecordedJanuary-February 2020
StudioSound City Studios
Length9:34
LabelColumbia
Songwriter(s)Bob Dylan
Producer(s)None listed
Audio
"Key West (Philosopher Pirate)" on YouTube
Rough and Rowdy Ways track listing
10 tracks
  1. "I Contain Multitudes"
  2. "False Prophet"
  3. "My Own Version of You"
  4. "I've Made Up My Mind to Give Myself to You"
  5. "Black Rider"
  6. "Goodbye Jimmy Reed"
  7. "Mother of Muses"
  8. "Crossing the Rubicon"
  9. "Key West (Philosopher Pirate)"
  10. "Murder Most Foul"

"Key West (Philosopher Pirate)" is a song written and performed by the American singer-songwriter Bob Dylan and released as the ninth track on his 2020 album Rough and Rowdy Ways. It is a mid-tempo, accordion-driven ballad that has been cited as a high point of the album by many critics.

Background and release

In June 2020, Bob Dylan released the album Rough and Rowdy Ways, his first album of original material since Tempest in 2012. Tempest had been followed by three albums of covers from the Great American Songbook. Meanwhile Dylan had continued to play live on his "Never Ending Tour", and had been awarded the 2016 Nobel Prize in Literature. The tracks for Rough and Rowdy Ways were written by Dylan at his home in Point Dume in late 2019 and early 2020.[1] The songs were recorded at Sound City Studios in Los Angeles in January and February 2020.[1]: 722 

Apart from Dylan, who sang, and played guitar and harmonica,[1] the musicians for the album included guitarists Charlie Sexton and Bob Britt, bass player Tony Garnier and drummer Matt Chamberlain.[1] On "Key West (Philosopher Pirate)", Donny Herron played accordion,[2] and Benmont Tench was on Hammond organ.[3] Some critics have compared the music to Dylan's melancholy 1989 love song "Most of the Time".[4][5] The song lasts for 9 minutes and 34 seconds.[1]: 726 

A bar stool with Bob Dylan's name painted on it in Captain Tony's Saloon

An article in Keys Weekly remarked upon how the song appeared to be written with an "insider's knowledge" of Key West, Florida, as the lyrics reference "landmarks Mallory Square and Bayview Park as well as the island city's Amelia Street and storied history: 'Truman had his [winter] White House there'". The article also quotes Joe Faber, the owner of Captain Tony's Saloon, who said that Dylan used to "come in here, sit and hang out” when the venue was owned by the city's "colorful former mayor" Tony Tarracino. As a result, the bar contains a stool with Dylan's name painted on it.[6]

Historian Douglas Brinkley confirmed that Dylan, who was "very good friends" with Key West resident and fellow songwriter Shel Silverstein, has frequented Key West "off and on throughout his life".[7] Brinkley characterized the song as "an ethereal meditation on immortality set on a drive down Route 1 to the Florida Keys".[2] Dylan has also expressed admiration for the work of longtime Key West resident Jimmy Buffett, covering "A Pirate Looks at Forty" in concert,[8] and citing the songs "Death of an Unpopular Poet" and "He Went to Paris" as his favorite Buffett compositions in an interview.[9]

Critical reception

Rolling Stone ranked "Key West" the second best song of 2020 (behind only Cardi B and Megan Thee Stallion's "WAP")[10] and placed it seventh on a list of "The 25 Best Bob Dylan Songs of the 21st Century".[11] In an article accompanying the latter list, music journalist Rob Sheffield extrapolated from the impressionistic lyrics a narrative about "a grizzled outlaw, hiding out in Florida, hounded by his memories".[11] Hyperallergic's Lucas Fagen wrote that, "in a voice drunk on blood and sunshine, Dylan sings a rapturous, almost operatic ode to the island, going overboard in his praise" but notes that the song "resonates thanks to the specificity and absurdity of its conceit" and calls it "emotionally direct and weirdly moving".[12]

Among the reviewers who have cited it as the high point of Rough and Rowdy Ways are the New Yorker's Amanda Petrusich, who called it "Shakespearean" for its lyrical richness and complexity,[13] and Anne Margaret Daniel at Hot Press, who wrote that "'Key West (Philosopher Pirate)' is what I'd take to my desert island"/[14][15][16][17][18]

Authors Adam Selzer and Michael Glover Smith have drawn thematic parallels between "Key West" and Harold Arlen and Yip Harburg's "Over the Rainbow"[19] and Dylan's own "Murder Most Foul", respectively. Smith also praised Donnie Herron's accordion playing on the track, which he cites as "the aural personification of a gentle Florida breeze, warmly embodying the 'healing virtues of the wind' that Dylan so memorably sings about".[20] Historian Douglas Brinkley, who conducted the only interview with Dylan to coincide with the release of Rough and Rowdy Ways, described the song as "a beautiful piece of art", adding that "Dylan knows it's my favorite on the CD".[21]

Spectrum Culture included the song on a list of "Bob Dylan's 20 Best Songs of the '10s and Beyond". In an article accompanying the list, critic Kevin Korber praises the "dreamlike" lyrics, in which he sees Dylan looking "beyond the realm in which we currently live... As Dylan approaches his eighties, it’s only fair that he would start thinking of what comes next, and 'Key West' could be the great singer coming to grips with what a paradise in the afterlife could be with only his terrestrial experiences to interpret from. Even so, he seems far from confident in his projections, perhaps understanding that these good times in this Florida resort town could be the best that life has to offer".[22]

The Big Issue placed it at #8 on a 2021 list of the "80 best Bob Dylan songs - that aren't the greatest hits" and called it a "[g]loriously meandering masterpiece from his latest album".[23] Edward Docx included the track in his 2021 list of "80 Bob Dylan songs everyone should know" in The Guardian.[24]

Rolling Stone critic Andy Greene acclaimed "Key West" as "the best song [Dylan has] written in at least the past decade"[25] Associated Press writer Scott Bauer found the song "breathtaking".[26]

Father John Misty named it as one of his favorite Dylan songs when providing a guest-curated playlist for the Jokermen podcast.[27]

Cultural references

The song's opening words, "McKinley hollered, McKinley squalled", refer to the opening of Charlie Poole's 1926 song "White House Blues", which describes the assassination of President William McKinley.[28]: 287 

In the second verse, the song's narrator identifies himself with a trio of famous Beat Generation writers: Allen Ginsberg, Gregory Corso and Jack Kerouac.[28]: 288–289  Ginsberg, who was close friends with Dylan,[29] once wrote a poem titled "Walking at Night in Key West".[30]

Dylan incorporates the titles of other popular songs into the lyrics of "Key West", including "Goin' Down Slow", "Down in the Boondocks", "Try a Little Tenderness", and "Beyond the Sea".[28]: 289–290 

Live performances

"Key West" received its live debut at the Riverside Theater in Milwaukee, Wisconsin on November 2, 2021, the first concert of Dylan's Rough and Rowdy Ways World Wide Tour. In a Rolling Stone review, Greene identified the performance as the "high point" of the show.[25] According to Dylan's official website, he had performed the song in concert 178 times as of December 2023.[31]

Accolades

Accolades for "Key West (Philosopher Pirate)"
Publication Accolade Rank Ref.
Rolling Stone The 50 Best Songs of 2020 2[10]
Rolling Stone The 25 Best Bob Dylan Songs of the 21st Century 7[11]
The Big Issue The 80 Best Bob Dylan Songs That Aren't Greatest Hits 8[32]
Spectrum Culture Bob Dylan's 20 Best Songs of the '10s and Beyond N/A[33]
The Guardian 80 Bob Dylan Songs Everyone Should Know[lower-alpha 1] N/A[24]

Notes

  1. ↑ List, excluding Dylan's best-known songs, by Edward Docx.[24]

References

  1. 1 2 3 4 5 Margotin, Philippe; Guesdon, Jean-Michel (2022). Bob Dylan All the Songs: The Story Behind Every Track (Expanded ed.). New York: Black Dog & Leventhal. ISBN 978-0-7624-7573-5.
  2. 1 2 Brinkley, Douglas (June 12, 2020). "Bob Dylan Has a Lot on His Mind". The New York Times. Archived from the original on December 8, 2020. Retrieved July 6, 2023.
  3. ↑ "The Heartbreakers' Benmont Tench Talks Touring and Recording with Bob Dylan". Archived from the original on May 13, 2022. Retrieved February 5, 2022.
  4. ↑ Fagen, Lucas (July 18, 2020). "Bob Dylan's Collage Artistry". Hyperallergic. Archived from the original on January 15, 2021. Retrieved February 5, 2021.
  5. ↑ "Bob Dylan Contradicts Himself". glidemagazine.com. June 23, 2020. Archived from the original on February 9, 2021. Retrieved February 5, 2021.
  6. ↑ Contributed (July 13, 2020). "Bob Dylan Immortalizes Key West on Latest Release". Florida Keys Weekly Newspapers. Archived from the original on January 16, 2021. Retrieved December 31, 2020.
  7. ↑ "Bob Dylan Unveils Poetic Song About Key West". Florida Keys Newsroom. Archived from the original on February 9, 2021. Retrieved February 4, 2021.
  8. ↑ Greene, Andy (July 5, 2016). "Flashback: Bob Dylan, Joan Baez Cover Jimmy Buffet in 1982". Rolling Stone. Retrieved February 4, 2021.
  9. ↑ Sterling, Colin (May 16, 2009). "Bob Dylan Exclusive Interview: Reveals His Favorite Songwriters, Thoughts On His Own Cult Figure Status". HuffPost. Archived from the original on September 8, 2021. Retrieved September 8, 2021.
  10. 1 2 Bernstein, Jonathan; Blistein, Jon; Dolan, Jon; Ehrlich, Brenna; Freeman, Jon; Grow, Kory; Hoard, Christian; Leight, Elias; Martoccio, Angie; Shaffer, Claire; Sheffield, Rob; Blake, Emily (December 7, 2020). "The 50 Best Songs of 2020". Rolling Stone. Retrieved December 9, 2020.
  11. 1 2 3 Dolan, Jon; Doyle, Patrick; Greene, Andy; Hiatt, Brian; Martoccio, Angie; Sheffield, Rob; Shteamer, Hank; Vozick-Levinson, Simon (June 18, 2020). "The 25 Best Bob Dylan Songs of the 21st Century". Rolling Stone. Retrieved December 9, 2020.
  12. ↑ Fagen, Lucas (July 18, 2020). "Bob Dylan's Collage Artistry". Hyperallergic. Archived from the original on January 15, 2021. Retrieved December 31, 2020.
  13. ↑ Petrusich, Amanda. "Bob Dylan's "Rough and Rowdy Ways" Hits Hard". The New Yorker. Retrieved December 31, 2020.
  14. ↑ Daniel, Anne Margaret. "The Verdict on Rough and Rowdy Ways by Bob Dylan: A Record We Need Right Now". Hotpress. Archived from the original on June 12, 2020. Retrieved April 4, 2021.
  15. ↑ staff/ben-yakas (December 29, 2020). "The Best Albums Of 2020". Gothamist. Archived from the original on December 31, 2020. Retrieved December 31, 2020.
  16. ↑ "Rough And Rowdy Ways is one of Bob Dylan's greatest albums". British GQ. June 23, 2020. Archived from the original on January 18, 2021. Retrieved December 31, 2020.
  17. ↑ Sheffield, Rob (December 17, 2020). "Year in Review: Rob Sheffield's Top 25 Songs of 2020". Rolling Stone. Retrieved December 31, 2020.
  18. ↑ "Danny McElhinney lists his artists of the year with his 2020 music review". Extra.ie. December 27, 2020. Archived from the original on December 27, 2020. Retrieved December 31, 2020.
  19. ↑ Selzer, Adam. "Dylan's 'Key West (Philosopher Pirate)': The Last Stop Before Kokomo". Adam Selzer's Blog. Archived from the original on January 18, 2021. Retrieved December 3, 2020.
  20. ↑ Smith, Michael Glover (December 1, 2020). "The Best of 2020: Dylan's "Key West (Philosopher Pirate)"". White City Cinema (blog). Archived from the original on January 28, 2021. Retrieved December 30, 2020.
  21. ↑ Brinkley, Douglas (July 8, 2020). "New Bob Dylan Song is Ode to 'Enchanted' Key West". Keys Voices. Archived from the original on January 21, 2021. Retrieved December 3, 2020.
  22. ↑ Korber, Kevin (February 19, 2021). "Bob Dylan's 20 Best Songs of the '10s and Beyond: 'Key West (Philosopher Pirate)'". Spectrum Culture. Archived from the original on February 26, 2021. Retrieved March 4, 2021.
  23. ↑ MacKenzie, Steven (May 17, 2021). "The 80 best Bob Dylan songs – that aren't the greatest hits". The Big Issue. Archived from the original on May 17, 2021. Retrieved May 18, 2021.
  24. 1 2 3 Docx, Edward (May 22, 2021). "Beyond Mr Tambourine Man: 80 Bob Dylan songs everyone should know". the Guardian. Archived from the original on May 22, 2021. Retrieved May 22, 2021.
  25. 1 2 Greene, Andy (November 3, 2021). "Bob Dylan Launches New Era of Never Ending Tour at Captivating Milwaukee Opener". Rolling Stone. Retrieved November 4, 2021.
  26. ↑ Bauer, Scott (June 17, 2020). "Dylan, Young release masterful albums". p. A2.
  27. ↑ Laffer, Evan (September 12, 2023). "Mindset Tapes". Jokermen Podcast Patreon. Retrieved September 12, 2023.
  28. 1 2 3 Gray, Michael (2021). "Rough and Rowdy Ways". Outtakes On Bob Dylan: Selected Writings 1967-2021. Pontefract: Route Publishing. pp. 252–297. ISBN 978-1-901927-86-3.
  29. ↑ "The friendship between Bob Dylan and Allen Ginsberg". faroutmagazine.co.uk. May 12, 2021. Retrieved September 13, 2023.
  30. ↑ Planer, Lindsay. "Holy Soul Jelly Roll: Poems & Songs". AllMusic. Archived from the original on July 7, 2023. Retrieved July 6, 2023.
  31. ↑ "Key West (Philosopher Pirate)". Bob Dylan's official website. Retrieved August 30, 2023.
  32. ↑ "The 80 best Bob Dylan songs – that aren't the greatest hits". The Big Issue. May 17, 2021. Archived from the original on May 17, 2021. Retrieved May 19, 2021.
  33. ↑ "Bob Dylan's 20 Best Songs of the '10s and Beyond". Spectrum Culture. February 19, 2021. Archived from the original on February 26, 2021. Retrieved March 17, 2021.
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