pfr, I watched a Tim Minchin concert on Amazon and was pretty much done half way through. I did like him as Atticus Fetch on "Californication".
Bill Bailey I only know from Black Books, very funny but not musical.
Now Flight of the Conchords, I love those guys and never tire of them. "Issues" is classic and when Britt in the guise of The Rhymenoceros raps "Ain't no party like my nana's tea party" I just about spit my coffee.

As to the premise of this thread, I'm reminded of a guy who was really popular when I was young, Jim Croce. Songs like "Don't Mess Around with Jim" and "Roller Derby Queen" have long since lost there charm and if I never hear "Leroy Brown" again it'll be too soon. On the other hand songs like "Time in a Bottle" and "It Doesn't Have to Be This Way" are moving and timeless.