The cheesier the better.
Doobie Brothers on What’s Happenin’? Not really cheesy. Doobie’s were way ahead of Metallica on copyright infringement. And they were nice about it.
And with hat tip to Sampiro from The Jackson Family is at it Again thread:
Married…with Children: “My Dinner With Anthrax”
“I see you’ve invited some killers over!”
Chad and Jeremy (as “The Redcoats” on The Dick Van Dyck Show
Frank Zappa on The Monkees
While it’s not super cheesy, David Bowie on Extras is my favorite. He sings starting at 1:16.
Aimee Mann on BtVS.
“Man, I hate playing vampire towns.”
Roger Daltrey appeared on That 70’s Show, CSI, and Witchblade.
Davy Jones on the Brady Bunch
Portlandia - Aimee Mann is our cleaning lady
Not sure if it counts, but any number of them on The Simpsons.
This is somewhat obscure, and not so cheesy, but the wonderfully rude British comedy The Young Ones had musical guests in almost every show, from Madness to Motorhead. One I’m especially fond of is the fun Amazulu (though they didn’t do my favorite song by them, “Cairo”).
I also liked Rip Rig + Panic’s appearance too, even with a different singer. The usual lead singer for RR+P was Neneh Cherry, (years before she came out with the now-dated but still relevant “Buffalo Stance” and (my favorite by her as a solo artist) “Manchild”) though the singer in that particular clip is Andrea Oliver.
Now I’m going to be remembering and chuckling at Young Ones lines.
"Darling fascist bully boy,
Give me some more money, you bastard."
Joe Walsh appeared in seven episodes of the Drew Carey Show. Once as himself and six times as “Ed,” a guy who Drew hires to play guitar in his band.
This has got to be the winner. I forgot about it, but it is just so bizarre and Aimee plays it so well.
So doesn’t fit the cheesy factor except for the amusing idolization by her employers.
Not as himself, but David Bowie did the voice for Lord Royal Highness in the extended length SpongeBob SquarePants episode “Atlantis SquarePantis”. The character had one green eye and one blue eye, playing off the popular belief that Bowie has two differently colored eyes (not true–his eyes appear different because one pupil is permanently dilated due to an injury).
And Highlander.
I nominate Billy Gibbons (ZZ Top) as Angela’s dad in Bones.
It seems like maybe Walsh is originally from Cleveland, like Drew Carey is; Maybe they know each other that way?
Glenn Frey appeared in the Miami Vice episode titled “Smuggler’s Blues”, named after his song.
My first thought was Cyndi Lauper’s Emmy for Mad About You. And she was a hoot on Bones.
The Dukes of Hazzard had many musical artists as guest stars.