Mark, what impressed me most about your post is that you remembered all those songs 'on the fly' ...

I've recently had requests for Red River Valley and Clementine, and what I've done is play them in the original style and then in 'updated' styles like these:
https://youtu.be/76OSOg5E_HE

https://youtu.be/gKxjvlEQvaQ

I've done the same thing with Little Star, playing the 1958 #1 hit version by The Elegants, 5 guys I knew in my Staten Island high school days
https://youtu.be/l8F4vdF-bJc