Christine Lavin is a ‘folk comedy’ singer- I went to one of her live shows a few decades ago and, along with Weird Al, added her to my “I need a laugh” selection of music.
I do have proper playlists so my comedy doesn’t get mixed up with my heavy metal or Christmas music, but for the long drive I just picked ‘shuffle the whole lot’ and skipped any that didn’t seem fitting when they popped up. The Doris Day and a few others are nods to Mrs. Ubergeek, who is partial to show tunes and that kind of thing. I skipped a bunch of those (sorry, honey!), but a couple of the Doris Day songs I enjoyed enough to let play through.
One of those Doris Day tunes was a bit of time travel cultural shock: “A Guy is a Guy”. Yikes- I had to listen to that to make sure it was as completely inappropriate in a modern context as it seemed at first to be. Definitely would not fly today: but it has a nice beat and you can sing along! Eeesh….