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Funny: Bob Dylan
  • "Positively 4th Street" is funny in just how plain BRUTAL it is.
  • Most of the Basement Tapes songs have some funny turns of phrase ("the comic book and me, just us, we caught the bus."), but a couple can be classified as full-on comedy and are absolutely hilarious: a doo-wop parody called "I'm Your Teenage Prayer" and a bit where Dylan and The Band deliberately slaughter a Mexican ballad.
    • They turn the Stylistic Suck Up to Eleven on the Ode to Intoxication "Bourbon Street". Bob cheers on a painfully bad trombone solo (probably played by Rick Danko): "Play it pretty now, boys! Sounds MARVELOUS!...A ton of joy! I can't take it no more!"
  • On The Bootleg Series VI: Live 1964, recorded just as Dylan was trying to break free of the Protest Singer mold, he is very clearly baked to the gills and in a very good mood. For instance, his reaction to an audience member requesting "Mary Had A Little Lamb".
    Oh my GOD. Did I record that? Is that a Protest Song?
  • The travails of the narrator of "Just Like Tom Thumb's Blues" get rather amusing, even if you feel sorry for the poor sap. His Screw This, I'm Outta Here! reaction to end the song caps off the tour de force.
    • Same goes for "Stuck Inside of Mobile With The Memphis Blues Again", except the situations are more surreal. Don't you hate it when you go to send a letter only to find someone stole the post office?
  • "Foot of Pride", for all its Crapsack World-ness, is hysterically funny.
    He looked straight into the sun and said "Revenge is mine!"
    ...But he drinks, and drinks can be fixed.
    Yeah, up on the stage they'll be tryin' to get water out of rocks
    A whore will pass the hat, collect a hundred grand and say "thanks."
    They like take all this money from sin, build big universities to study in
    Sing "Amazing Grace" all the way to the Swiss banks!
  • "Pay In Blood" has some hilariously cruel lines:
    You got the same eyes as your mother does
    If only you could prove who your father was
    • and
    I've been through hell, what good did it do?
    You bastard! I'm supposed to respect you?
  • "Brownsville Girl":
    Even the swap meets around here are getting pretty corrupt
  • "Highlands" is a 16-minute rumination on mortality, morality and failure... in the middle of which, Dylan pops into a diner and gets into a bizarre argument with the waitress, who thinks he's a famous painter and refuses to let him go until he draws her. The section ends with Dylan running out without paying and returning to his Serious Philosophizing.
    Then she says, “I know you’re an artist, draw a picture of me!
    I say, “I would if I could, but I don’t do sketches from memory.”
    “Well,” she says, “I’m right here in front of you, or haven’t you looked?”
    I say, “All right, I know, but I don’t have my drawing book!”
    She gives me a napkin, she says, “You can do it on that”
    I say, “Yes I could, but I don’t know where my pencil is at.”
    She pulls one out from behind her ear
    She says, “All right now, go ahead, draw me, I’m standing right here.”
    I make a few lines and I show it for her to see
    Well, she takes the napkin and throws it back and says, “That don’t look a thing like me!
    I said, “Oh, kind Miss, it most certainly does.”
    She says, “You must be jokin’.” I say, “I wish I was!

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