I'll accept two correct answers for my Cab Calloway photo, but man, it might take a while for the correct answer that was my first thought to be posted.
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Scatman!Cryptic hint: "Cab Man"
You still won't get it.
Edit to add another photo of the same person in the first photo. But the first image is the one that is intended to invoke the idea of a certain song.
View attachment 2774096
Yes - Roundabout
Sitting on the Edge of the World - Fogerty
Sitting on the Edge of the World - Fogerty
View attachment 2774113
The easiest one: