DOING THE MATH
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OK, assuming it's true that the impending tsunami of retiring boomers will create new musical opportunities, the next question is "How do I know which songs to prepare?"

I've noticed that most peoples' musical taste is formed in high school, and they tend to retain a special affection for songs that were popular the year they graduated.

Except for special cases like government workers who often get early retirement packages, the vast majority of Boomers will retire between ages 62 and 65

That means the group retiring this year probably graduated from high school between 1964 and 1967

Searching the web for the top 100 pop songs for those years, we find:

http://www.musicoutfitters.com/topsongs/1964.htm
http://www.musicoutfitters.com/topsongs/1965.htm
http://www.musicoutfitters.com/topsongs/1966.htm
http://www.musicoutfitters.com/topsongs/1967.htm

If you pick your first batch of songs from these 4 lists, you'll probably be in the ballpark and able to offer songs that the current group of retirees wants to hear.
Then each year, get the next list and learn another batch of songs from it. That way, you'll always stay current with the fresh crop of retired boomers.


(A lot of these songs may already be on your song list since if you're reading this you're probably at or approaching retirement age too)

https://www.dropbox.com/sh/ey71h8ep047758h/AAC12jNM0Hz9Q8zsh5iDeqNHa?dl=0