John Lennon
Jim Morrison
Roy Clark. He had such talent that he could play difficult pieces with ease all the while adding comedic touches and making funny faces. Of course he was the grinnin’ part of pickin’ and grinnin’.
How are you defining “funny”? Funny in interviews? Funny lyrics? Laughing-out-loud funny, or smirk funny?
I think “Weird Al” Yankovic is funny. And Frank Zappa. But in very different ways.
My vote for the funniest, though, is Jon Lajoie.
Mason Williams
Banjo-playing Steve Martin has to be at the top of the list.
And the Blues Brothers and their band.
Peter Schickele/ P. D. Q. Bach – I suspect a lot of his musical jokes went un-noticed by the general public, so he played P.D.Q. Bach pretty broadly, so people would get the joke. He was a graduate of Julliard.
He also wrote non-comic stuff. He did the score for the movie Silent Running. He also wrote over 100 pieces of various types of music.
There’s also Spike Jones, and a few other older musical comedians whose names escape me right now.
Aha! Here’s one! Anna Russell and her deadpan dissections of opera – Anna Russell - Wikipedia
He stole his act from the Hoosier Hotshots. And, in turn, got it stolen by Weird Al.
Homer and Jethro were the country version.
Bette Midler.
You might want to give more context, or link to a site about the Hotshots (like this obvious one – Hoosier Hot Shots - Wikipedia )
I don’t know anything about the Hotshots, but saying that Weird Al stole Spike Jones act suggests to me that you’re not familiar with either Jones or Yankovic, or maybe both. Although both did their own original comic songs, Jones’ schtick was really weird renditions of pop tunes (“Cocktails for Two”), while Weird Al did parodies of current pop songs using the original music (or sometimes hijacking the melodies of pop songs to parody cultural movements). The acts aren’t the same at all.
Loudon Wainwright III is very funny in concert and has some great funny songs withe depth to them.
The Bonzo Dog Band is the gold standard of funny music in the rock era. Basically, they’re the Monty Python of music. Or, rather, Monty Python is the Bonzo Dog Band of sketch comedy – the Pythons were heavily influenced by them.
Some examples:
The Intro and the Outro
Look Out, There’s a Monster Coming (cameo by Terry Jones)
Death Cab for Cutie (introduced by Michael Palin). They also performed this on the Beatles Magical Mystery Tour.
Doctor Jazz
There’s also Martin Mull, who put out several very funny albums in the early 70s, with songs like “Licks Off of Records.”
Not quite as well known is Blotto, with “I Wanna Be a Lifeguard,” “We are the Nowtones,” and “Metal Head.”
I am quite familiar with them all, thank you. A distinction between a weird rendition and a parody seems like a fine one, even without considering that both did both.
They were mostly a local act from Boston’s North Shore, but The Fools will always have a place in my heart with “Life Sucks, Then You Die”, “Psycho Chicken”, and “Big Big Big”.
Mojo Nixon and Skid Roper’s “Elvis Is Everywhere” deserves a mention, too.
No mention of Kinky Friedman yet? The man’s songs and detective books are a laugh out loud treasure.
Not at all. Weird al didn’t do weird renditions, AFAIK – he changed the words to make his points, but retained the melody and rhyme scheme (and, if he did a video, the basic structure). Spike Jones’ weird renditions kept the words, but went ape with the music. That you think these are identical, or even close, baffles me.
Shel Silverstein is best known as a writer, but he recorded some of his stuff, too. I trust you all know his style.
Perhaps you need to listen to more of both. A good idea in any case.
Define it any way you want, variety is good. I really love funny in an interview setting.
Bret McKenzie and Jemaine Clement (Flight of the Conchords)