Music

5 of Bob Dylan’s All-Time Worst Songs

Bob Dylan receives well-earned praise for his songs. Not all of them can be successful, though. Here are some of his worst songs.

by Emma McKee

Published on March 11, 2023

2 min read

Bob Dylan is one of the most prolific songwriters of all time, but even he has songs that don’t measure up with the rest. Some of them have incomprehensible lyrics, and others are outright mean, especially because they were written about real people. Here are five of Dylan’s worst songs.

Bob Dylan wears a black vest and plays a song on the guitar. — Bob Dylan | Bob King/Redferns

5. ‘Ninety Miles an Hour (Down a Dead End Street)’ is a yawn-worthy Bob Dylan song

Dylan did not write the 1988 song “Ninety Miles an Hour (Down a Dead End Street),” but his rendition was not worth the album space. Though not penned by Dylan, the song is slow and dull, and the lyrics overwork the central metaphor.

While it’s not Dylan’s worst song of all time, “Ninety Miles an Hour (Down a Dead End Street)” is blandly forgettable.

4. ‘T.V. Talkin’ Song’ is overly obvious

One of Dylan’s greatest strengths as a songwriter is his subtlety and wit. “T.V. Talkin’ Song” lacks these qualities. The song is a condemnation of television and technology in general, and its message is obvious to an eye-roll-worthy degree.

Beyond that, the production could be better, leaving the song sounding messy. It appeared on 1990’s Under the Red Sky, one of Dylan’s more disappointing albums, and it feels at home there.

3. ‘Ballad in Plain D’ is a song even Bob Dylan regrets

The 1964 song “Ballad in Plain D” is an over eight-minute-long meditation on Dylan’s relationship with Suze Rotolo. In it, he also details his contentious relationship with Rotolo’s sister, Carla, including a screaming match between the two of them.

“Beneath a bare lightbulb the plaster did pound/ Her sister and I in a screaming battleground,” Dylan sang.

He goes so far as to sing that he “had no respect” for Rotolo’s “parasite” sister. The song is a one-sided account of a breakup that lacks the depth of many of his other songs. Even Dylan ultimately admitted that he regretted writing it.

“That one I look back and I say, ‘I must have been a real schmuck to write that,'” Dylan told Bill Flanagan in the book Written in My Soul. “Of all the songs I’ve written, maybe I could’ve left that one alone.”

2. ‘Ugliest Girl in the World’ is repetitive and mean-spirited

Dylan co-wrote the 1988 song “Ugliest Girl in the World” with Robert Hunter, and, as the title suggests, it is about Dylan being in love with the ugliest girl in the world. Dylan sings about her “ugly” attributes and then asserts that he loves her despite them.

The song is shallow, misogynistic, and mean-spirited. It’s also repetitive and feels beneath Dylan as a songwriter. According to his official website, he has never played the song live, so it’s possible that he agrees.

1. ‘Wiggle Wiggle’ is widely considered one of Bob Dylan’s worst songs

The title itself is enough to turn away a listener, but anyone brave enough to press play on Dylan’s 1990 song “Wiggle Wiggle” is sure to be disappointed. In it, Dylan encourages the listener to “wiggle, wiggle, wiggle like a swarm of bees,” “a bowl of soup,” and “a big fat snake,” among other things.