Cyndi Lauper is mentioned in the OP.
If this is an "enjoyable romp (!) through the history of music" then perhaps each episode won't just focus on one person as per Life on the Road.
LOL! That reminds me of Randy Newman. He always used to do little introductions to his songs which were even funnier than the songs themselves. I think it was in 1992 when he played "I just want you to hurt (like I do)", and said he wanted it to be this big charity thing like "We are the world", with good celebrities, where he would get a chance to sing, "without Cyndi Lauper ripping away the microphone all the time".
The cd is called 12 songs twice, very recommendable!