I turn 65 in a few days, and I've seen a lot.
My first record player had no electronics. It plugged into the wall, but the only electric part was the motor. The sound came from a diaphragm on the tonearm that vibrated sort of like a kazoo. The player came with two sets of styli (or needles as we called them) "soft" and "loud" which was the only way to change the volume. My parents never let me use the "loud" needles.
Records were all 78 rpm, except the "story" records were 16rpm.
Since then, 45rpm singles, then 33rpm albums, cassettes for trading music with friends or taping off the radio, then CDs, now digital files without physical media. I never did the 8-track thing, and missed some formats that never caught on e.g. the el-cassette, the mini-disc, the DCC, etc. Tubes were never a thing for me.
For pro use, open reel 1/4" two track, followed by a brief period of VHS HiFi along with an even briefer flirtation with the Sony F1, eventually settling on DAT for live recording until retiring from the pro audio world.
Were there any moments that stood out to you? Anything that blew you away the first time you heard it?
It was all pretty incremental, no real "aha" moments. Buying my first real stereo at 16 was a big deal, moving to DAT from the previous analog formats was a giant step forward, and so was the move from razor blades to DAWs, but as I say, basically incremental.
From a historical perspective, the invention of electrical recording just about 100 years ago was the single biggest step forward in audio quality. Take a listen to a 1924 recording vs a 1927 recording and the difference is remarkable. Everything else is basically just a footnote.