BobFest: 12 Funniest Dylan Songs

This is twelve more on top of the five that Rolling Stone picked, which includes the awesome "Bob Dylan's 115th Dream." Some of Dylan's songs can be unintentionally humorous, like, say, "Sweetheart Like You." Others have humorous undertones even if the main idea is on another level; I think "4th Time Around" is pretty funny if you get right down to it. But all of these are funny on purpose, even the first one:

All The Tired Horses (Self Portrait)

This one also belongs on the list of "Bob Dylan's Worst Songs" – but just because it's terrible doesn't mean it's not a joke. There a sense in which the entire Self Portrait album is one big cruel joke - Bob has more or less copped to the fact that he made it really bad on purpose, in order to scare off some of his more rabid fans. Like that worked.

Clothes Line Saga (Basement Tapes)

Always one of my favorites, the laconic tale of a nice lad whose laundry duties are interrupted by news of the vice-president's sudden descent into madness.

It's All Good (Together Through Time)
From his most recent studio album, the cynical Elder Bob smiles through his sneer as he employs a contemporary cliche in service of his kvetching.

Leopard Skin Pillbox Hat (Blonde on Blonde)
You know, it balances on your head just like a mattress balances on a bottle of wine.

Lo and Behold (Basement Tapes)
A lot of the Basement Tapes released so far are pretty damn goofy, but none of them are goofier than this one. Makes me wanna take my kids camping and sing it 'round the fire.

See Ya Later Allen Ginsberg (Basement Tapes outtake)

A lot of the unreleased Basement Tapes are even goofier. Dylan and the Band crack themselves up ad-libbing a takeoff on the Bill Haley chestnut "See Ya Later Alligator." Also recommended is the absurdist take on "Teenage Prayer."

Sittin on a Barbed Wire Fence (Bootleg Series Vol. 1-3)

Recorded in 1965, released in 1998. This Highway 61 outtake is ripe for a blistering cover version - even though you're gonna think this song is a cliff. 

Talkin' Bear Mountain Picnic Massacre Blues (Bootleg Series Vol. 1-3)
Now we come to the "Talkin'" songs, each funnier than the last one. In this epic tale, Bob takes the family on vacation and ends up in the middle of the Hatfields and McCoys.

Talkin' Hava Negiliah Blues (Bootleg Series Vol. 1-3)
This is just a tossed-off improv, but it's the intro that makes it: "Here's a foreign song I learned in Utah"

Talkin' John Birch Paranoid Blues (Bootleg Series Vol. 1-3)

Now we all agree with Hitler’s views

Although he killed six million Jews

It don’t matter too much that he was a Fascist

At least you can’t say he was a Communist!

That’s to say like if you got a cold you take a shot of malaria

Hmmm.. I wonder why they wouldn't let him perform it on the Ed Sullivan Show?

Talkin' World War III Blues (The Freewheelin' Bob Dylan)
Kind of like the flip side of "A Hard Rain's A-Gonna Fall." Who knew the Cuban Missile Crisis was such a lark?

TV Talkin' Song (Under the Red Sky)
Dylan wanders through Hyde Park in London and hears a preacher ranting about the evils of television: "It will scramble up your head and drag your brain about/Sometimes you gotta do like Elvis did and shoot the damn thing out."

Full lyrics over at Bob's place.