The Worst Bob Dylan Song from Each Decade

Bob Dylan is so prolific that he must have some “worst” songs. 

Let’s face it. With over 500 tunes to his credit, they can’t all be great. Right?

Today, we’re looking at this iconic storyteller’s worst songs from each decade. 

Let’s dive in!

About Bob Dylan

Bob Dylan was born Robert Allen Zimmerman on May 24, 1941, in Duluth, Minnesota. His early musical influences came from listening to country and blues music on radio stations out of Shreveport, Louisiana. As a teenager, he began listening to rock and roll.

Dylan’s music covers a vast array of musical genres. His most significant contribution to the music scene is the passion and opinion found in the lyrics of his American folk songs. Bob’s writing certainly reflects his personal experiences in life and commentary on political, social, and cultural movements. 

He’s also a 2016 Nobel Laureate in literature. The committee expressed his award as “… for having created new poetic expressions within the great American song tradition.”

At the age of 81, Dylan still performs his unforgettable style on the Never Ending Tour, now called the “Rough and Rowdy Ways World Wide Tour, 2021-2024”. 

While Bob Dylan arguably has a number of misses, these are the ones we chose from his six-decade career. Why nothing from this decade? We’re only two years in! Come back to us in another eight years.

The 1960s – Ballad in Plain D

About the Song: Bob Dylan wrote a Ballad in Plain D after a breakup with Suze Rotolo. The song recounts a final argument between Suze, her sister Carla, and Bob. It seems full of self-pity, with no successful resolution to his angst.

Dylan is known for expressing his personal experiences through his art. And it appears Rotolo wasn’t offended by the lyrics, reflecting the song may be Dylan working through the upsetting time.

The song is painful, eight minutes and 18 seconds long. Bob himself regrets writing it. He told Bill Flanagan in 1985, “… of all the songs I’ve written, maybe I could have left that alone.” 

Worst Lyric: The song has 13 verses. He shows how much he didn’t like Suze’s sister with this worst line, “For her parasite sister, I had no respect.” We must agree with Bob on this one. You probably should have left this alone.

First Appearance: Dylan released Ballad in Plain D as part of his 1964 album titled Another Side of Bob Dylan by Columbia Records.

The 1970s – Joey

About the Song: Dylan wrote Joey in collaboration with Jacques Levy, a New York theatre director and songwriter. The piece recounts the life and death of mobster Joey Gallo, who was gunned down on his birthday in Little Italy (New York City.)

Critics of the song felt it was too sympathetic to a man with a violent history, accused of at least two murders and convicted of several felonies. Controversial, some people felt Joey glorified violence and romanticized gang culture.

Dylan responded to this accusation in 2009 by saying that Jacques wrote the words, and he merely sang them. 

Worst Lyric: Joey lasts 11 minutes, and the worst lyrics are in the chorus. Since Gallo was a mobster, why would you sing, “What made them want to come and blow you away?”

First Appearance: Between 1987 and 2012, Dylan played this song 82 times, according to his website. Joey is part of Dylan’s 1976 album, Desire with Columbia Records. 

The 1980s – Ninety Miles an Hour (Down a Dead End Street)

About the Song: Hal Blair and Don Robinson wrote the lyrics for Ninety Miles an Hour. The pair is best known for their songs written for Elvis Presley and his 1960s movies.

The piece is a basic lament of forbidden love between two people committed to others. Several artists have covered the song, including John Denver, Tommy Womack, and The Blackeyed Susans.

Most critics agree that Bob Dylan’s version with the original lyrics is slow and unrehearsed. Ninety Miles an Hour implies a tempo Dylan never reaches. The cleverest part of the song is the title and chorus, “Ninety miles an hour (down a dead end street).” Dylan’s delivery makes it regrettable. 

Worst Lyric: The worst lyrics for us are, “… now I have no choice,” and “It’s too late to listen to that warning voice.” We disagree. You always have the choice to listen. 

First Appearance: The first release of Ninety Miles an Hour was by performer Hank Snow in 1963 on the RCA Victor label. It’s on Dylan’s album Down In The Groove, released in May 1988 by Columbia Records.

The 1990s – Wiggle Wiggle

About the Song: The song’s title, Wiggle Wiggle, makes us wince. We thought this might be part of a Dylan pinned children’s book, but it was another slip. Wiggle Wiggle misses the mark compared to his well-known brilliance in songs like Desolation Row and Abandoned Love.

Wiggle Wiggle is the opening song on Dylan’s album Under the Red Sky. Perhaps he conceived this as a line dance to be played well into a wedding reception’s evening. It’s a tired tune that’s uninspired. 

Worst Lyric: Critics found the line, “Wiggle wiggle wiggle like a bowl of soup,” proof Dylan was off his game. The worst lyric for us was simply, “Wiggle wiggle wiggle,” used annoyingly over 50 times. 

First Appearance: Columbia Records released Wiggle Wiggle and the album Under the Red Sky on September 10, 1990.

The 2000s – Sugar Baby

About the Song: Bob Dylan’s inspiration for Sugar Baby is from the Gene Austin and Nathaniel Shilkret classic The Lonesome Road. Dylan borrows the melody and arrangements while including new lyrics and an additional chorus.

Dylan aficionado Tony Attwood (Untold Dylan) laments this rendition of the classic. He finds the song too sad with lyrics like, “Some of these memories you can learn to live with and some of them you can’t.” YouTubers, however, love the tune for this very reason.

Worst Lyric: We agree the song is rather slow and sad. The worst lyrics for us are found in Dylan’s chorus.

“Sugar Baby, get on down the line
You ain’t got no sense, no how
You went years without me
Might as well keep going now”

First Appearance: Sugar Baby is track 12 on Love and Theft, released in 2001. 

The 2010s – Roll On John

About the Song: Bob Dylan wrote and performed Roll On John as a tribute to Beatles legend John Lennon.

The two performers met in 1964. Many believe the song’s origins are from Dylan’s tour of Lennon’s childhood home in Liverpool, England.

Critics like how Dylan tells the story of Lennon’s life through references to his upbringing and Beatles lyrics. A five-star review by Will Hermes (Rolling Stone) named Roll On John as one of the most powerful cuts on the album. However, USA Today ranked 359 Dylan songs and listed this one as 337. Ouch. 

Worst Lyric: “Sailin’ through the trade winds bound for the South, Rags on your back just like any other slave.” Is he trying to compare Lennon’s life with that of enslaved African people? Not cool, Bob.

First Appearance: Two songs have the same title, the first performed in 1962. The John Lennon tribute, Roll On John, is the final track from Dylan’s 2012 album Tempest on the Columbia label. 

Which Song is Bob Dylan’s Worst?

Rolling Stone, USA Today, and Time listed Wiggle Wiggle in the top ten least favorite Dylan songs. This one and Joey are the worst Bob Dylan songs, in our opinion. Bob Dylan’s loyal fan base may disagree. 

Dylan’s folk-style storytelling and personal life expression may not work for every lyric. The musician himself reflects on some of his works from the eighties, saying his talent was not under control.

Be honest. What do you think is Dylan’s worst song?