Top Lists: Bob Dylan’s Funniest Songs

Not only is Bob Dylan one of the most visually striking poets of music, he’s also one of the funniest. Though he’s known more for his serious political songs, Dylan also has a sense of humor, highlighted by this list of funny and witty songs. Some of these songs will make you laugh out loud, but they’ll all put a smile on your face.

Here’s Bob Dylan’s funniest (or wittiest) songs.


“I Shall Be Free No. 10”

Try not to laugh the first time you hear Dylan say “He’s a weird monkey. Very funky.”


“Motorpsycho Nitemare”

A funny tale of someone trying to escape a crazy man’s farm. Also, Dylan’s love for Fidel Castro and his beard is revealed.


“Rainy Day Women #12 & 35”

Is there a double meaning to getting stoned? Doesn’t matter, the song is still funny as hell.


“Talking Bear Mountain Picnic Massacre Blues”

I will never go to Talking Bear Mountain after hearing this hilariously disturbing retelling of a strange incident.


“Subterranean Homesick Blues”

The song is more vicious than funny, but you’ll still chuckle when you hear, “Get jailed, jump bail, Join the army if you failed.”


“Talking World War III Blues”

It’s the end of the world and all Bobby wants is to find some company. You’ll feel sorry for him but you’ll laugh at his disposition.


“With God On Our Side”

Not so much funny as it is witty, this is one of Dylan’s most visually striking songs.


I couldn’t find videos on Youtube for “Rainy Day…”, “Subterranean…”, or “Talking…” – I guess that means you’ll have to go out and buy the albums to hear the songs 🙂

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