Spinal Tap
Noel “Paul” Stookey of Peter, Paul, and Mary was funny enough for the record company to give his patteran entire side of a live album.
“…and four six-packs.”
“We’ll take it!”
Kevin Griffin from Better than Ezra is hilarious in his acoustic solo act.
Also, Jim Kerr from Simple Minds. Usually old age jokes.
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Also AC/DC, perhaps not surprisingly, have always been funny in their Howard Stern interviews as well as Ringo Starr.
Henry Rollins does a standup act (I know he prefers “spoken word”) that’s very funny too.
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I was not a fan of Mac Miller’s music, but he was a very funny guy. RIP
He’s quite funny on the 1964 Town Hall Concert official bootleg.
People were shouting out requests. One shouted “Mary had a Little Lamb.”
Dylan: Is that a protest song?
Plus quite a few of his songs were funny, like Talkin’ John Birch Society Blues, I Shall be Free (original and # 10) and Talkin’ World War III Blues.
By 1966, not so funny.
Him.
Keith Moon. Without question.
Which brings to mind Tom Paxton. How could a man whose biggest hit was Thank You Republic Airlines and whose first song ever written was The Marvelous Toy not be considered Funny?
Weird Al? Tenacious D? Flight of the Conchords?
Yep. They are my favorite. My wife and I often break out singing one of their songs.
It’s business
It’s business time
When I’m down to my socks it’s time for business
That’s why they’re called business socks, oh
Leo Kottke - Long funny rambling anecdotes between songs to fill time spent retuning guitar to different setups.
Ian Anderson - Very witty and quippy in interviews.
David Lee Roth - Infectiously manic and happy.
Cab Calloway - Hepcat-slang infused love for his art.
Jimmy pop from the bloodhound gang.
We’ve gotten this far down and no one has mentioned Tim Minchin?
No love for Carrie Brownstein? I mean, I get that Portlandia isn’t a universal taste, but she starred in a well-known comedy series that ran for eight seasons.
Jazz singer and guitarist John Pizzarelli is very funny, both on stage and on his radio show.
It surprised the heck out of me, but punk icon and actor Henry Rollins is a very funny speaker. He is more of a story teller than a stand-up comedian and most of his youtube stuff can be found by searching his name and “spoken word.” (Having trouble linking on my phone.)
Louis Jordan. Not a comedian as such, but for example, “There Ain’t Nobody Here But Us Chickens.”
David Lee Roth is an interesting guy, even if many of his answers are the same and pre-planned, he was very creative and just an interesting guy to see in an interview. I checked out his radio show, but not much, didn’t grab me like I expected it to, but I’m sure I can find something, maybe the right topic.