Weekly Playlist: Bob Dylan Special Edition (1/14/2025)
Photo Courtesy of Bob Dylan Spotify
Bryce Russell 2025 | Art & Entertainment Editor
With the new movie A Complete Unknown starring Timothée Chalamet chronicling Bob Dylan’s rise in the folk music scene of early the 1960s and his turn to electric rock in 1965, I figured I’d focus on one of the greatest songwriters of all time. I’ve been a Bob Dylan fan for a long time, ever since my dad made me listen to “Like a Rolling Stone” back in eighth grade, so for this week’s playlist I’m going to highlight some of his less popular but no less brilliant songs from multiple eras of his career. So, if you saw the movie and wanted to explore some Dylan songs that were not featured in the movie, this playlist is for you.
“Drifter’s Escape” from 1967’s John Wesley Harding
Just as Dylan deviated from his expected path in 1965 by turning to electric rock music after securing his place as the country’s most popular folk musician, Dylan did so again in 1967. After his fabled motorcycle accident (which may or may not have happened, and may or may not have been as serious reports said), Dylan retreated from the spotlight for a time and returned with John Wesley Harding. The album, most well known for featuring “All Along the Watchtower” which would be reinvented by Jimi Hendrix a year later, featured semi-solo acoustic songs more akin to his earlier folk music than the electric music from just two years prior. “Drifter’s Escape” is my favorite off the album, a deceptively simple and short song telling the story of a man’s escape from a courtroom amidst chaos and lightning.
“Boots of Spanish Leather” from 1964’s The Times They Are A-Changin’
This is one that I wish was featured in the new movie. My favorite song from this era of Bob Dylan, it tells the story of a person who leaves their lover behind as they travel to Europe. Dylan introduced it in a concert in 1963 as a “when you can’t get what you want you have to settle for less kind of song.” Inspired from his relationship with Suze Rotolo (who is featured in the movie under a new name Slyvie Russo), I was sure this would make the movie. Featuring gentle fingerstyle guitar picking and more reserved, soft vocals from Dylan compared to other work, “Boots of Spanish Leather” is a perfect song in every single way.
“Wedding Song” from 1974’s Planet Waves
A last ditch attempt at saving his marriage with his wife Sara Lownds, “Wedding Song” is one of Dylan’s most personal songs. Featured on Planet Waves, the only studio album featuring the Band, a band who was linked with Dylan since his famous electric tour in 1966, Planet Waves has a reserved, roots rock sound with songs primarily inspired by his family. “Wedding Song” has become one of my most played Bob Dylan songs recently, with its simple guitar strumming and passionate harmonica. Although a love song, the atmosphere is dark and foreboding, perhaps foretelling his coming separation and divorce.
“She’s Your Lover Now” outtake originally recorded for 1966’s Blonde on Blonde
This is the era of Bob Dylan that first got me hooked. Recorded for Blonde on Blonde, the last album of what became known as the “electric trilogy,” this era was described by Dylan as having a “thin, wild mercury sound,” and though I might not totally understand what exactly that means, the image it generates fits this song perfectly. “She’s Your Lover Now” was left off the album and not officially released until the first volume of the Bootleg Series archival releases. The song features Dylan’s classic cryptic and often bizarre lyrics, but still creating a cohesive narrative of a man singing to both his ex and her current boyfriend. I’ve linked an extra version of this song as well. This slower version is more complete, containing more lyrics and one of my favorite Dylan lines “now your eyes cry wolf while your mouth cries I’m not scared of animals like you.” Both versions are fantastic.
“Black Diamond Bay” from 1976’s Desire
Written, as were all songs on Desire, alongside songwriter Jacques Levy, “Black Diamond Bay” is one of Dylan’s greatest narrative achievements. The song tells the story of the doomed town of Black Diamond Bay and its residents’ troubles which become trivial as the town is destroyed by a volcanic eruption. The final verse is from the perspective of a man watching the events unfold on the evening news, but ultimately not caring because it’s a town halfway across the world and has no bearing on him. I think this is one of Dylan’s most resonant in today’s world, with constant news of tragedies around the world, and how often no one really seems to care, and sometimes it’s hard for yourself to even care. Desire has a distinct feel to it, with beautiful violin work that is unique to this album.
“Make You Feel My Love” from 1997’s Time Out of Mind
Now most connected with Adele due to her cover of it on her debut album 19, “Make You Feel My Love” was released on Dylan’s 1997 comeback album Time Out of Mind. “Make You Feel My Love” is one of Dylan’s best love songs about pining for someone who may not feel the same way about you, and everything you would do to have them love you. The gentle piano and Dylan’s older, grisled voice join together perfectly.
“Is Your Love in Vain?” from 1978’s Street-Legal
Street-Legal was critically panned when it was released. After the acclaimed Blood on the Tracks from 1975 and Desire from 1976, Street-Legal deviated from Dylan’s sound by bringing in a horn section and a choir of backup singers. In recent years however, it has been looked on more favorably, and I think “Is Your Love in Vain?” is one of the best on the album. If you like this one, I’d also recommend “Changing of the Guards” and “Señor (Tales of Yankee Power)” off this album.
“Spanish Harlem Incident” from 1964’s Another Side of Bob Dylan
1964’s Another Side of Bob Dylan is often overlooked. Falling between his amazing third album The Times They Are A-Changing and the first electric album Bringing It All Back Home, Another Side is not quite as good as those two, but has some very good folk songs on it. “Spanish Harlem Incident” is one of my favorites, describing a narrator who is completely captivated by a girl he sees in Spanish Harlem for only a fleeting second.
“Up To Me” outtake originally recorded for 1975’s Blood on the Tracks
Blood on the Tracks is often considered Bob Dylan’s first “comeback” album. After a string of critically panned or (seemingly) lackluster albums from the late 60s to the early 70s, 1975’s Blood on the Tracks showed that Dylan still had the magic touch. The final album has a full band sound, with overdubs and drums, but this song, “Up To Me,” was only recorded in the solo acoustic style that was the original vision of the album, and sadly didn’t make the cut for the final album.
“Blind Willie McTell” outtake originally recorded for 1983’s Infidels
Infidels was Dylan’s first album after a trio of gospel albums that lasted from 1979 to 1981. Though not necessarily a return to form or a comeback album, it has some bright points. However, the best song, “Blind Willie McTell,” was left off the final album. Named and inspired for Blind Willie McTell (who was name dropped in the new movie), a blind blues guitar picker who recorded music from the late 1920s and through the 1930s, it is a reflection on the origin of American music (particularly the blues), and history of race in the history of the United States.
“Just Like Tom Thumb’s Blues” from 1965’s Highway 61 Revisited
I think “Just Like Tom Thumb’s Blues” has Dylan’s best opening line: “When you’re lost in the rain in Juarez, when it’s Easter time, too.” That sets the stage for one of Bob Dylan’s absurdist masterpieces. If you watched the movie, this is the album that contains “Like a Rolling Stone,” marking a turning point not just in the music of Bob Dylan but in American music in general. The song has no chorus, and recounts the narrator’s experience in Juarez filled with drugs, alcohol, poverty, and various escapades before deciding to return to New York City.
“I’ve Made Up My Mind to Give Myself to You” from 2020’s Rough and Rowdy Ways
This song was released on what I keep calling Dylan’s “new record,” although at this point it’s 5 years old now. His first album of original material since 2012’s Tempest, it became Dylan’s first album to top any Billboard chart, and featured some of his strongest writing of the 21st century. “I’ve Made Up My Mind…” is one of my favorite songs from the album, and Dylan’s aged voice meshes great with the almost big band aspect of the song, reminiscent of music by artists like Frank Sinatra.
“Summer Days” from 2001’s Love and Theft
This song is a straight up rockabilly song in the style of some of Dylan’s heroes like Buddy Holly and Chuck Berry. Coming off of Love and Theft, the follow up to his 1997 comeback album Time Out of Mind, “Summer Days” and the rest of Love and Theft was more upbeat, but showed that Time Out of Mind wasn’t just a fluke, and that Bob Dylan was back (if he ever left).
“On the Road Again” from 1965’s Bringing It All Back Home
Bringing It All Back Home was the first album of Dylan’s electric period. Split in two halves, the first side of the album featured an electric band while the back side featured solo acoustic material. “On the Road Again” is on the first half, and is a blazing blues song, with unhinged lyrics and harmonica. The lyrics are absolutely bizarre, but that is why it’s so fun.
“Every Grain of Sand” from 1981’s Shot of Love
“Every Grain of Sand” is the standout track from 1981’s Shot of Love, which was Dylan’s final album of a three album run of Christian Gospel music. The song, probably the best from that era, is a beautiful reflection on God and humanity.
“Under the Red Sky” from 1991’s Under the Red Sky
“Under the Red Sky” is the standout title track from Dylan’s 1991 album. Featuring George Harrison of the Beatles on guitar, this song is one of the few songs from the album of the same name that I come back to. While not the best album, the song shows that even in periods in Dylan’s history that dip below his best work, he can still make some brilliant tracks.
“Can You Please Crawl Out Your Window?” released in 1965 as a non-album singleI think this is my favorite Bob Dylan song. Recorded during the sessions that spawned Highway 61 Revisited, it wasn’t put on the album but was released as a single in 1965. Along with “Positively 4th Street” and “Like a Rolling Stone,” “Can You Please Crawl Out Your Window?” is about similar subject material (and maybe the same specific person) and has Dylan addressing the hypocrisy of people and the folk scene around him. I also really enjoy this demo version.