I have a pair or ports pros. Great quality and super comfy for the price iirc they went out if business not too long ago.

Never could afford PortaPros as a kid, now as an adult I tend to enjoy them quite much.

They where in Mad Men, but never heard of them before:

Bet they were! I only had Realistic headphones like that in the 80s and even those were mind blowing. Also had the first, tiny, Sony Walkman headphones and couldn’t believe how good they were.

I’m no audiophile, but I don’t think much has improved on this front.