I will add this one, my Tekna T2100 circa 78 or so. Not my oldest obviously but old enough.
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My usual regulator is 30 years old, a ScubaPro Mark V from 1979. Older than I am, ha! It was one of the many pieces of my father's vintage dive gear (including my cherished JetFins) that he bestowed upon me when I got certified.
Here's a pic of me using it on a photoshoot at a local theme park:
My only complaint is that it's a little heavy and (as you can see) tends to sag and pull on my jaw. Eventually I'm going to buy a lighter-weight reg for primary use, but this will always be one of my favorites (even if it is a pain in the neck to find a place to service it!)
I also have an old funky Dacor, which I believe is a few years older than this one. But I don't trust it and wouldn't actually use it. It makes for a nice conversation piece, though.
Edit to add: It's also worth noting that I have the original owner's manual and warranty/service card (in my father's name) for the ScubaPro reg, too! Heck, I even have an old ScubaPro sticker that came with it, too! (My family never throws anything out, apparently.. ha!)