"Bob Dylan's 115th Dream" (Bringing it All Back Home, 1965)
Herman Melville meets Henny Youngman in this frisky tour of American history. Dylan's deadpan comic timing is perfect: "I ordered some suzette / I said, could you please make that crepe?"
"If You Gotta Go, Go Now" (The Bootleg Series Vol. 1-3, 1991)
Dylan requests a little girlie action, laughing his way into her pants. In the Philharmonic Hall version from Halloween 1964, he has the crowd rolling in the aisles from the intro ("I have my Bob Dylan mask on") to the final come-on: "I'll be sleeping soon, and it'll be too dark for you to find the door."
"Tweeter and the Monkey Man" (Traveling Wilburys-Volume 1, 1988)
When the Traveling Wilburys album came out in 1988, this outrageous self-parody landed on the fan community like a bomb, from the Springsteen jokes to the fact that it beat the crap out of any song he'd put on any of his own albums lately. Rumors that this song inspired the plot of The Big Lebowski have never been confirmed.
"I Want You" (Blonde on Blonde, 1966)
Poor Bob – hounded by the ladies, coaxed into their beds, when all he really wants is to get back to ... what was your name again? The final verse where he fumbles for rhymes – "because he liiied, because he took you for a riiide, uh, because time is on his siiiide" – might be his funniest moment ever.
"Po' Boy" (Love and Theft, 2001)
The poet of his generation turns into a Borscht Belt stand-up, stealing gags from Groucho Marx ("calls down to room service, says send up a room") and busting out a knock-knock joke. Try the veal, folks – it's so good William Zanzinger ordered seconds!