I guess I am one of the few who will mix Cab Calloway, Mozart, Bob Wills, Phantom of the Opera and Perry Como on my CD player, and spend the rest of the day in Hog Heaven!
I also do that, but I group songs by year. In the folder for 1950 on my 1950's flash drive, for example, you will hear Jo Stafford singing a soulful love song, Charline Arthur and Kitty Kallen singing dance tunes, Hank Willims, Tex Williams and Arthur Smith threatening Stalin with nuclear war, Ernst Busch praising Stalin, and a Soviet chorus celebrating the Sino-Soviet Treaty of Friendship and Alliance.
You’re not alone.
With Apple Music + Sirius XM, I find most of my listening starts at the 70s & goes back to the 40s.