4 of the Weirdest Songs by Bob Dylan

Bob Dylan has been known for delivering some unexpected pieces of work through the years. Most of that work ended up being chart-topping hits and folk rock staples that made him as famous as he is. However, Dylan did have a few run-ins with bizarre inspiration; and the resulting songs were simply weird. Let’s look at four of the weirdest songs by Bob Dylan!

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1. “Ugliest Girl In The World”

This 1988 song came from a somewhat enigmatic album from Dylan. Down In The Grove was a little bit of a disappointment among some of the fanbase, as was the previous album Knocked Out Loaded. It was a collaborative album. Yet, even multiple hands and voices couldn’t quite lift this album up to Dylan’s other, more notable works—admittedly a tall task. “Ugliest Girl In The World” was written with Robert Hunter (of Grateful Dead fame). The result was a very weird, straight-up rude song about falling in love with a girl with unconventional features.

2. “Polka Dots And Moonbeams”

This newer track from Bob Dylan’s 2016 record Fallen Angels is more than worthy of a spot on our list of his weirdest songs. It’s worth noting that the song is a cover, as is everything on this particular album. Most of the record featured Great American classics, but it also featured a few oddballs. “Polka Dots And Moonbeams” was originally written by Johnny Burke and recorded by Frank Sinatra and follows a similar formula as “Ugliest Girl In The World”; though it’s slightly nicer to the enigmatic woman in question.

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3. “If Dogs Run Free”

“If Dogs Run Free” is a great song in its own right, complete with a hypnotizing piano intro and jazz melody. What makes it odd is the scat singing break that kicks in at an odd time. New Morning was a polarizing album to begin with, and throwing this “experimental” track into the mix just made it odder.

4. “Bob Dylan’s 115th Dream”

This song is definitely story-based, but the frenzy of it all makes it one of Bob Dylan’s weirdest songs of all time. It tells the story of policemen, French women, Christopher Columbus, Captain Arab, a cow, and more. It’s unrestrained and manic, and it feels like more spoken word than song at times.

Photo by Steve Morley

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