The Worst Bob Dylan Songs, According to His Own Fans

Even Legends Have Missteps

When it comes to songwriting legends, Bob Dylan’s name almost always tops the list. Since emerging in the 1960s as a voice of protest and poetic reflection, Dylan has reinvented himself countless times — from folk icon to electric rocker to gospel storyteller. His career spans more than six decades, filled with celebrated albums and timeless songs that reshaped modern music.

Still, even Dylan’s most loyal fans admit he’s not immune to the occasional misfire. On the online forum r/bobdylan, a dedicated community of Dylan enthusiasts recently debated which songs they consider his worst. The results were surprisingly unanimous — and at times, brutally honest.

“If Dogs Run Free” – New Morning (1970)

Many listeners praise this 1970 New Morning track for its experimental charm. The lyrics are thoughtful, and the laid-back jazz arrangement — complete with acoustic guitar and a walking bassline — gives it an easy, late-night feel.

But for some fans, it’s not the composition that misses the mark — it’s the delivery. “The backing vocals ruin it imo,” wrote the original poster. The song features a wildly unrestrained female scat vocal layered over Dylan’s spoken-word performance, creating a mix that many find hard to take seriously. What might have been a mellow jazz experiment instead turned into a quirky novelty that divides fans to this day.

“Ugliest Girl in the World” – Down in the Groove (1988)

This track from Down in the Groove feels like a parody of a Bob Dylan song. With tongue-in-cheek lyrics about falling for “the ugliest girl in the world,” it’s hard to tell whether Dylan was in on the joke or not. His delivery — a nasal drawl over slick, overproduced blues-rock — doesn’t help its cause.

One Redditor summed it up harshly: “Terrible lyrics, awful production and mix, uninspired singing and music… absolutely nothing good to say about it.” The song’s cartoonish tone and awkward humor left many fans scratching their heads, wondering how it ever made the final cut.

“Wiggle Wiggle” – Under the Red Sky (1990)

Then there’s “Wiggle Wiggle,” a track that manages to be both infamous and oddly beloved. Some fans jokingly defend it, saying, “If by worst we mean best, then I’d say Wiggle Wiggle.” The lyrics — “Wiggle ’til it whispers, wiggle ’til it hums / Wiggle ’til it answers, wiggle ’til it cums” — raised eyebrows, especially coming from the man once called “The Voice of a Generation.”

Still, there’s a certain charm to its rockabilly rhythm and tongue-in-cheek delivery. Featuring Slash on lead guitar, it sounds like Dylan having a bit of fun — maybe too much fun. As one YouTube commenter dryly noted, “This man won a Nobel Prize.” And somehow, that just makes “Wiggle Wiggle” even funnier.