Bob Dylan, “Talking Bear Mountain Picnic Massacre Blues”
With his current dour demeanor, it’s easy to forget how funny Dylan can be. He and his make-believe family go on one doozy of a picnic in this Bootleg Series howler. The talking blues format was borrowed, but the jokes are all Dylan’s.
Choice line: “It wasn’t much of a picnic … didn’t come close to a mountain … and I hate bears!”
See also: “Talking World War III Blues,” “I Shall Be Free,” “Bob Dylan’s 115th Dream”
Johnny Cash, “A Boy Named Sue”
Humorist and children’s author Shel Silverstein wrote the words to this one, but only Johnny Cash could weave the tale. He really sells the drama of this poor kid whose father named him Sue, just to be a dick.
Choice line: “My name is Sue, how do you do! Now you gonna die!”
See also: “Flushed From The Toilet Of My Heart,” “One Piece At A Time”
Simon and Garfunkel, “A Simple Desultory Philharmonic”
Paul Simon imitates his main rival in this high brow send-up of mid-Sixties culture, filled with in jokes and bold faced names. “I must have dropped my harmonica, Albert” is a reference to you know who.
Choice line: “I’ve been Roy Hayleed and Art Garfunkeled.”
See also: “Punky’s Dilemma,” “At The Zoo”
Arlo Guthrie, “Alice’s Restaurant”
Arlo Guthrie’s most famous tune takes up one whole side of an album. Thanksgiving dinner with the relatives can drag on forever, but this epic story-song, which clocks in at 18:34, is entertaining the whole way through.
Choice line: “Yes, sir, Officer Obie, I cannot tell a lie, I put that envelope under that garbage.”
See also: “Motorcycle Song”
Jimi Hendrix – “Taking Care Of No Business”
“All I got to my name is a beat-up guitar and three broken strings,” groans Hendrix in this vaudeville-style drunkard’s lament. While he wasn’t a fan of his own vocals, half the humor is in his houndog delivery.
Choice line: “I’m so broke, I can’t even pay attention.”
Country Joe and the Fish, “Fixin’ To Die Rag”
Give me an F! This anti-war Woodstock anthem is a sly takedown of the “conflict” in Vietnam; proving a spoonful of sugar goes a long way in the protest department.
Choice line: “Be the first one on your block to have your boy come home in a box.”
“Weird Al” Yankovic, “Eat It”
For many kids in the ‘80s, “Weird Al” was their favorite comedian. “Eat It,’ his high-calorie parody of Michael Jackson’s mega-hit “Beat It,” helped propel the king of polka-rock to global superstardom.
Choice line: “Get yourself an egg and beat it.”
See also: “Amish Paradise,” “Smells Like Nirvana”
Beck had us laughing from the moment he burst onto the scene, covered in metaphorical cheese wiz. Like much of his early work, the rap-blues rock hybrid “Loser” is a junk-collector’s collage of surrealistic imagery.
Choice line: “In the time of chimpanzees, I was a monkey.”
See also: “Satan Gave Me A Taco,” “Debra”
Dan Bern, “Talking Woody, Bob, Bruce & Dan Blues”
Folk singer Dan Bern sets out to visit an ailing Bruce Springsteen, as Dylan once famously did with Woody Guthrie. The only problem – The Boss is still in perfect health.
See also: The Walk Hard Soundtrack
Choice line: “Go forth and be the voice of your generation.”
Lonely Island, “Lazy Sunday”
Lonely Island started a social revolution with the video for “Lazy Sunday,” Andy Samberg and Chris Parnell’s hardcore, gangsta rap paean to going to the movies and eating cupcakes.
See also: “I’m On A Boat,” “Ras Trent”
Choice line: “Google Maps is the best. True that. Double true!!!”
Tenacious D, “Tribute”
“This is not the Greatest Song in the World, this is just a tribute.” A metal-riffic update on “Devil Went Down To Georgia” that’s heavy on the hysterics.
Choice line: He asked us, “Be you angels?” “Nay. We are but men.”
See also: “Wonderboy,” “Master Exploder”
Flight Of The Conchords, “Business Time”
There’s no such thing as an unfunny Flight of the Conchords song, but we’re partial to “Business Time,” an audio aphrodisiac that celebrates the fact that Wednesday is “hump day” without ever spelling it out.
Choice line: “Two minutes in heaven is better than one minute in heaven.”
See also: “Bowie,” “Foux du Fafa”
LCD Soundsystem, “Losing My Edge”
With LCD Soundsystem, you come for the beats, and stay for the surprisingly brilliant lyrics. What happens when the coolest kid on the block grows up to be a middle-aged man? He loses his all his indie cred.
Choice line: “I heard you have a compilation of every good song ever done by anybody.”
See also: “Drunk Girls”
Hayes Carll, “She Left Me For Jesus”
Channeling sardonic songwriters like John Prine and Randy Newman, Hayes Carll spins a wry and dusty tale of failing to measure up to the new man in his woman’s life: Jesus! He threatens violence, but we don’t see that working out too well.
Choice line: “The last time we made love, she even called out his name.”
See also: “Another Like You”
What are some of your favorite funny songs? Let us know in the comments.