Mismatched Songs for Mismatched Performers?

[Reasley]

Mismatched Songs for Mismatched Performers?

I was just replying to another thread and wanted to start a new thread on the topic of mismatched songs/mismatched performers. Here's what I mean. Let's do the thread like this:

Demographic of Performer:
Song:
Song Artist:
Venue:
Demographic of Audience:
Why Not?

I'll start:

DoP: 60ish Babyboomer male
Song: Handyman
Artist: James Taylor covered it
Venue: Wine bar, restaurant, wedding reception
Why not?: Listen to the lyrics: "Hey, girls, gather 'round . . . I'm your handyman"

Related, I've often thought that it would be hilarious to "rewrite" the lyrics of "Thinking Out Loud" for babyboomer performances, e.g.:

"Darlin', I'll be lovin' you 'til I'm 93 . . ."