I didn't actually KNOW any of them, but the Springsteen one triggered immediately..

Hmm, that's a hint of a mustache, maybe it's freddie mercury - yes!
Hmmm, that's a bike, maybe purple rain, yes!
Hmm, that skin tone is 2 light for 2 of them, yes, got it!
WTF is that frilly shit, looks like part of a dress, hmmm, Madonna, yes!

I lucked out for the magic age. My brother, 3 years older, guided most of my choices, and his favorite time frame was 65-70s, and most of those bands were still in active production.

I played name that tune in jail. I'd pace the block, and there were 2 guys arguing over a radio at one end. Hey you, name that tune. I'd spit it out after a bar or 2. For hours and hours. I rarely got it wrong.

Did the same when listening to music with the boy. We'd compete to see how fast/fewest notes needed to figure it out.