Most Important Dylan Songs By Half-Decade

Knowing that I am a self-described “neurotic Bob Dylan devotee,” my co-editor Nicholas Austin Ferrell suggested that I do some sort of list of Bob Dylan songs by decade. I liked the idea, and I decided to work on a list of what I think are the most important Bob Dylan songs by decade. Once I sat down to work on the list, however, I realized that I should go by five-year intervals instead of ten because there are so many Dylan songs worth noting.

Before continuing, this list is of course my opinion, and I may leave out some great Dylan songs that you think should have been included. Furthermore, because this is my list of most important Dylan songs by decade, it is not necessarily a list of my favorite Dylan songs – in many instances I had to eschew my favorites for what I think is more “important” to his catalogue of songs.

If you have thoughts or disagreements, I welcome feedback in our Guestbook.

1960-1965: “Blowin’ in the Wind”

I admit “Blowin’ in the Wind” is not my favorite Bob Dylan song. Of the protest era Dylan, I prefer “The Times Are a’ Changing” – or something like “The Ballad of Hollis Brown,” or a deep cut like “John Brown.”    But it is too culturally significant to omit here. “Bowin’ In The Wind” is an essential part of the American music canon and an anthem of the civil rights movement.    It’s famous, and it’s important – I’d argue it helped folk music go mainstream.

“It’s Alright Ma (I’m Only Bleeding)”

Because Dylan was so prolific in the early 60s, I decided to add a second song for the most important Dylan songs from 1960-1965.  Although “It’s Alright Ma (I’m Only Bleeding) isn’t electric, it reflects the marked transition between Dylan’s folk persona and his electric persona. Like “Mr. Tambourine Man” and similar works, it was an obvious departure from Dylan’s preceding topical songs, both music and lyrics. The sheer psychedelic nature of this song is on par with Dylan’s writing style in the coming years. The song shows Allen Ginsburg’s influence on Dylan, and I’d argue that this was the stepping stone between Woody Guthrie inspired Dylan and 60s revolution Dylan. 

Dylan himself also describes “It’s Alright Ma (I’m Only Bleeding) as one of his most important songs, containing a type of magic that he doesn’t know how he captured.    Listen to it, or just read it – the song is freaking mind blowing from a poetic standpoint.

1965-1970: “Like A Rolling Stone”

This is the song that folks screamed “Judas,” at him for. His keyboard player in the documentary “No Direction Home” recounts how fans would boo them, sing along with the song, and then continue to boo them after. While there are many masterpieces on both “Highway 61 Revisited,” and later “Blonde on Blonde,” that are in this style and genre, “Like a Rolling Stone” is the most famous song. The song reached No. 2 on the US Billboard chart, right under The Beatles’ “Help.” Much like “Blowing in the Wind,” this song is part of the American lexicon.

“Desolation Row”

“Desolation Row,” the closing track of “Highway 61 Revisited,” merits honorable mention as one of Dylan’s most important songs from 1970-1975. It’s an eleven minute and twenty one second song that cryptically weaves in characters from pop culture, history, and mythology. The song includes famous figures, both real and fictional, including, among others, Albert Einstein, Robin Hood, T.S. Elliot, Cinderella, the Phantom of the Opera, and Ophelia. These characters make appearances and then exit the stage never to return – but each contributes to the song’s larger picture.  It’s a marker for Dylan, the beginning of a stylistic change. It also puts Dylan’s ability to craft long and compelling songs on display for the first time.

1970-1975: “Tangled Up In Blue”

The late 60s were rough for Dylan. Let us just say that he went through some stuff.    Dylan left the electric years behind and went country with albums “John Wesley Harding” (1967) and “Nashville Skyline” (1969). There was a departure from the psychedelic writing that pervaded “Highway 61 Revisited” and “Blonde on Blonde.” But then, after a painful divorce from his first wife, Dylan created “Blood on the Tracks,” a true masterpiece featuring solo acoustic songs, as well as acoustic-driven material recorded with local musicians from Dylan’s home state of Minnesota.

While I adore every track on “Blood on the Tracks” and could listen to this album until everyone around me goes insane – the title track “Tangled Up In Blue” is the most important. The song contains hints of the old psychedelic Dylan as he recounts a cryptic story of love loss, pain, and growth. “Tangled Up In Blue,” and the entire “Blood on the Tracks” album, are two of Dylan’s golden achievements.

1975-1980: “Hurricane”

Close after “Blood on the Tracks,” Mr. Dylan released “Desire,” an album also driven by an acoustic sound – this time featuring fiddle and a different kind of energy.    The song “Hurricane,” about the wrongful arrest of “Hurricane Rubin Carter,” shows a rare return to topical material for Dylan. The song actually played a role in freeing the boxer, and (while albeit not as much as the earlier mentioned “Like a Rolling Stone” and “Blowing In The Wind”) it became part of American pop culture. The surrounding tour, known as “The Rolling Thunder Revue” has recently been documented by Martin Scorsese in a documentary.

“Changing of the Guards”

After “Desire” things started to change for Dylan and his career. Dylan converted to Christianity and produced a series of poorer quality recordings, marking a downturn of sorts in his storied career. However, Dylan’s “Street Legal” album developed a strong following, of which I am a member. “Changing of the Guards” stands as Dylan’s most important song from the late 1970s. The writing recaptures the essence of Dylan’s psychedelic 60s phase, and the particular type of high energy with which he delivers the material isn’t something we have seen again. While this is not a list of my favorite Dylan works, “Street Legal” is like a strange ship in the night in a sea of poorly produced Dylan albums in the late 1970s.

1980-1985: “Dark Eyes”

Despite the poor production and arguably not grade-A material from albums like “Shot of Love” and “Empire Burlesque,” the album “Dark Eyes” is from, “Dark Eyes” is a gem for those who can get past the relatively subpar recordings. “Dark Eyes,” the final track on “Empire Burlesque,” is a solo acoustic track on an electric album. The song is a short and cryptic little poem which has been covered by other musicians, including Sam Beam of Iron & Wine.

1985-1990: “Ring Them Bells”

After some lean years in the late 1970s and early 1980s, Dylan returned with a vengeance with a new phase. His album, “Oh Mercy,” marked this change – the writing, the feel, and his voice began to mature into what we know today. While Dylan has departed from his Christian period, much of his material to this day has strong Christian undertones and overtones. However, instead of proselytizing, the Christian themes in Dylan’s later works have served as poetic inspirations. No song better captures Dylan’s transformation in the early 90s than “Ring Them Bells.”

1990-2000: “Love Sick”

The 1997 release of “Time Out of Mind” was a public resurrection for Dylan, and was received as the “Dylan-is-back” album.” The title track “Love Sick,” was performed at the Grammy’s (where a deranged fan infamously wrote “soy bomb” on his naked chest and wandered on to the stage). Dylan himself describes the song as one of his timeless songs. Songs of love loss and pain are timeless. “Time Out of Mind” as a whole is one of my many favorite Dylan albums.

2000-2005: “High Water (for Charlie Patton)”

While many fans describe Dylan’s new phase as a trinity of albums – “Time Out of Mind,” “Love & Theft,” and “Modern Times,” Dylan has offered his own two cents on the matter, stating that if one most define it as such – his new phase began with his 2001 album, “Love & Theft.” Unsurprisingly, Dylan is right. The conjurer of ancient spirits Dylan phase, producing material heavily inspired by songs rooted in the folk and blues tradition, begins here. 

I choose “High Water,” as the “important song” for “Love & Theft” because it is easy to trace its roots. Dylan draws on the work of early blues legend “Charlie Patton,” reviving and reinterpreting the material. This becomes how Dylan has continued to create to the present and while it has also made him the center of plagiarism scandals, I return to my folk musician argument: it’s the job of a folk musician to keep the tradition alive.

2005-2010: “Thunder on the Mountain”

“Modern Times” was Dylan’s first #1 Billboard album since “Desire” in 1967. It also made Dylan the oldest artist to top the Billboard chart. “Modern Times” continues Dylan’s deep dive into folk and blues, but is decidedly more “electric” than it’s predecessor, “Love & Theft,” and is a culmination of Dylan’s “new” sound – a sort of earthy-rockabilly band.    “Thunder on the Mountain” is the title track, so I chose it to represent the album. All the songs on the album are, to say the least, quite good.

2010-2015: “Tempist”

Dylan continued his theme with 2012 release of “Tempest,” which features a thirteen minute and fifty-four second ballad by the same name about the Titanic sinking. Dylan answered why he wrote a song about the Titanic by saying something to the effect that every folk musician needs a song about the Titanic sinking.    At his root, Dylan is, and always was, a folk singer. “Tempest” is particularly clever in that Dylan chose to weave fact and fiction together – making the cast of the famous movie “Titanic” present in the song.   The song includes references to the Leonardo DiCaprio, not the character he played in the movie “Titanic,” but “Leo” himself. Dylan astutely alluded to the fact that the movie about the Titanic sinking had become part of the lore.

2015-2010: “Murder Most Foul”

After Tempest, Dylan released a series of Frank Sinatra albums.    While these albums are great, and interesting from a musical perspective (taking a full brass band arrangement and breaking it down for a five-piece electric band) they are all eclipsed by the 2020 release of “Rough and Rowdy Ways.”

In “Rough and Rowdy Ways,” Dylan took what he synthesized from Sinatra and applied it to his own writing. He conjures recent characters – instead of resurrecting Charlie Patton, Blind Willie McTell, or civil war poet Allen Timrod, Dylan calls on Jimmy Rodgers, Jimmy Reed, and John F. Kennedy – whose assassination receives a sixteen minute and fifty-four second epic. Much like Desolation Row, we see characters come and go, all helping to paint a larger picture of life following J.F.K’s murder. These characters are people my father remembers, rather than spirits from the archives of history.   

The song is real, the song is present and relevant – and a return to Dylan’s topographical roots.    “Murder Most Foul” topped the billboard chart in its genre and has been received as a modern masterpiece. While all of Dylan’s recent original work (Time Out of Mind through Rough and Rowdy Ways) is all part of the same ilk and very good – “Rough and Rowdy Ways,” Mr. Dylan’s 39th studio album, is cut from a slightly different cloth, and I understand why folks are connecting with it more so than the others.

Conclusion

This concludes my list of the most important Dylan songs by five-year periods. While all of these songs are “important” both in the context of Dylan’s own career and also in the greater folk music context, they are all quite good. Give Dylan a listen – you won’t be disappointed.