Portable audio quality since the 80s.

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Photo By Binarysequence (Own work) [CC BY-SA 4.0 (http://creativecommons.org/licenses/by-sa/4.0)], via Wikimedia Commons

Gear centered audiophiles rave about portable audio players all the time, most follow reviews sites in the quest for the audio quality grail. Often young enthusiasts search for audio quality like its some illusive thing that only the newest most expensive players will deliver, but sound quality is not a new thing.
In-fact brands marketed portable audio quality since the start of the 80s.

Sony was the first one with the TPS-L2 Walkman at the beginning of the 80s, the now iconic blue and silver metal cased Walkman was the first of many in the successful line of cassette players the Japanese brand would ship around the world.
I never had the chance to hear the TPS-L2 player but would own a WM-FX421 (1998)  and have access to a WM-EX622 (1995) a friend had.
Both cassette players had good quality if my memory serves me right.
Later I would have a Discman D-171 (1995?) and a MZ-R35 MiniDisc Walkman (1998) in both cases the audio quality was on par with the digital audio players sold at stores these days.
In 2001 I would have access to a friends Creative Labs Nomad Jukebox also known in Europe as the Creative Digital Audio Player an amazing MP3 player at the time and also during that year I would hear a Apple Ipod for the first time.
Many other portable players I had the chance to hear are not listed, mostly because I don’t remember the models or because they are rather new like the Sony Playstation Portable Slim, Philips Opus 16Gb and Creative Zen Stone I own.

Sure I can’t confirm objectively my claims but all of these players had the sound quality you can find almost 15 years later in a typical off the shelf DAP or cellphone.
Quality did improve in the high-end gear that is now capable of driving very high impedance headphones at ease. Also High-resolution music is now the new trend because sound quality sells even if sometimes you might not actually hear it without very good headphones or a little help from an old musician.
The main difference to the gear of the old days is in the size of the tech, my MZ-R35 played a physical medium making it a fairly complex mechanical DAP.
Today’s tech in comparison is cheaper, thinner and physical medium free.
With solid state cards reaching hundreds of GBs in size, audiophiles are now free to take their full collections on the go without the need for carrying CD cases but with all the bits and bytes intact.

More than 3 decades ago Sony gave the masses Hi-Fi sound in a way the world never seen before, later Apple would revolutionize the way people interacted with their players and music collections and now the omnipresent smartphones are the new DAPs of the masses, the standalone DAP is now a niche product made for the ones who are still on the quest for the holly grail of portable audio.
Quality is now the rule not the exception.