An old geezer once asked me to play some Dylan. Wrong generation, mate. Your classics are not necessarily mine.
The oldest song I play is Every Breath You Take. Most of my set is stuff from the 90s. Losing My Religion, High And Dry. I might even throw in the odd Wonderwall or Don't Look Back In Anger to please the masses.
I had this group of lads once, stopped and sang along. Wanted me to do an Oasis medley. I didn't mind doing it. It was a laugh. You don't get many laughs as a busker.
Sometimes you might see a married couple and you get eye contact with the woman. On her way to M&S or Sainsbury's, the old man in tow. At that moment you feel like you're singing just to her. That's a sweet feeling, that connection. A sweet feeling.