Mostly you’re right, but Weird Al’s polka medleys are a lot closer to the kind of thing Spike Jones did.
I think a lot of people are taking this in a different direction than the OP intended. From the OP’s example, I don’t think he’s looking for comedy acts—people who made funny music—so much as for serious musicians who were/are funny, who had good senses of humor than didn’t necessarily come out in their music.
I didn’t know that Jim Morrison was funny, but I did know that all four Beatles, and especially Lennon, were (from their interviews, writings, etc.).
Weird Al is just channeling Frank Jacobs.
Yeah. Jim could be funny in some interviews, and was very funny sometimes in concert, shouting funny things to the crowd.
Jim Stafford, folks. Guy’s a total loon; I love him.
Pete Townshend has told some hilarious stories in between songs at solo gigs.
Ace Frehley from Kiss. It’s a really specific type of humor, but if you watch any old interviews with him, his laugh alone is hysterical - Joker-level insane. The fact that Gene Simmons and Paul Stanley seem like they can’t stand him makes it even better.
I’d second the vote for Mojo Nixon (and Skid Roper, even though he never said anything).
Perhaps surprisingly, I’ll suggest Richard Thompson. For many years, both as a member of Fairport Convention and as a solo act, he never said anything on stage and wrote “doom and gloom” songs almost exclusively. In recent years, he’s shown a terrific deadpan humor, both in on-stage banter and in his often humorous and totally original songs. His cover of “Oooops! I Did It Again” is hilarious.
Frank Zappa
John Lennon?
Run for Your Life? Jealous Guy? He is about as funny as a Moe Howard poke in the eye.
Oscar Levant.
With the passing of Bob Einstein, one has to think of the Smothers Brothers in this category.
I love “Hunting Tigers Out in Indiah” and have had “The Equestrian Statue” stuck in my head for days.
Spanning the ‘intentionally humorous songs’ and ‘funny stories in person/concert’ categories is Arlo Guthrie.
And, definitely in the ‘funny songs’ category is Tom Lehrer of course.
I think Rick Wakeman matches the spirit of the OP.
Check out his acceptance speech when Yes were inducted into the R&R Hall of Fame: https://www.youtube.com/watch?v=85PT2YgN780
Victor Borge was one of the funniest people of all time, period.
Both David Bromberg and Dan Hicks had many hilarious lyrics and songs, in addition to other styles.
Well played, well played.
I think Borge was the undisputed master of the comedic pause. It’s what always struck me when watching him. That deadpan delivery combined with perfect pauses before the punchlines. If you can find it, look up video for the joke about his uncle who invented a soft drink called “4-Up”. Wonderful pause.
Another example is the one liner he would begin by showing the audience his watch: “My grandfather gave me this watch on his deathbed [pause]… for twenty bucks.”