The Diamond Rio was amazing because it was seen by IT companies and the record labels as an illegal product. It spawned a lawsuit "Recording Industry Ass'n of America v. Diamond Multimedia Systems, Inc.". Without DMM winning this lawsuit (against all odds), there would be no MP3 players worldwide, there would be no iPod, there would be no iPhone, there would be no Apple as we know it today.

I had one of these badboys, which I filled with music from DC++ (those were the days.)

https://en.wikipedia.org/wiki/Archos_Jukebox_series

I wish I still had it so I could laugh at how big and heavy it is, with its 20gb spinning disk and those big blue rubber bumpers. Learned a lot putting different homebrew firmwares on it.

Also big shoutout to the Cowon iAudio series. Those things did sterling service for years. Just thinking of the brightly coloured menus is sending me back to my teenage days.

The Archos Jukebox was the player that introduced me to Rockbox[0]. Great player for the time, but as you said it was huge. I think I even put in a larger drive at some point.

These days I run rockbox on an iPod. The hardware is better but rockbox is still IMHO the best interface for a portable music player.

[0] http://www.rockbox.org

Oh man, I actually forgot I owned that. How could I forget? Those bumpers were so big and blue.

Not as old, but I still have my Sansa c250:

https://en.wikipedia.org/wiki/Sansa_c200_series

It's my most portable FM radio. I'd rather use the FM chip on my smartphone, I know it's there, but the manufacturer could not be bothered to enable it. So I keep my little Sansa around. Only had to replace the Li-Ion battery once.

Rockbox makes it even nicer:

https://www.rockbox.org/

That's the first one I had, a 128MB version I think. Great for riding a bike with because you could operate it without looking.

My Cowon iAudio 7 is still going strong, and I don't know what I'll do when it dies. I like having a standalone music player that plays ogg-vorbis, and presents as a mass storage device.

https://en.wikipedia.org/wiki/IAUDIO#iAUDIO_7

I got a free Rio 500 from the website PointClick during the height of .com insanity. That thing was easily one of the greatest consumer electronics products of all time.

Does anyone know the inside story of what ever happened to that product line? I read that Diamond sold the assets, but didn't find anything beyond that. (Though I would note that their earlier model, the PMP300, looks suspiciously like the first iPod.)

The Rio IP and engineers went to Sigmatel [1], who essentially turned the firmware for the Rio Karma into a reference firmware for their MP3 player SoCs. The Trekstor Vibez [2] was probably the most well-known player that used that platform.

By the way, the Karma firmware was really ahead of other players of the time, supporting perfect gapless playback, Vorbis and FLAC support, and on the fly playlist editing. The iPod never got on the fly playlist editing, which I really missed when I moved over to using one from a Karma.

[1] http://www.theregister.co.uk/2005/07/27/sigmatel_rio_deal/ [2] https://en.wikipedia.org/wiki/TrekStor_Vibez

The Rio 500 was the first MP3 player I ever used. I thought it was incredible :)

The Volt was the first MP3 player I ever owned. I loved that device. 700 MB of music, and I could burn as many CDs as I wanted... That thing was great.

Yes a rio. Those were great. And you could just mount 'em in linux without having to go through the dreadful apple software. Way better.

I was a college freshman going from home dial up BBS's to a major university's internet speeds. Ripped a bunch of CD's to that Diamond Rio and loved running instead of using my tape player to make running playlists. I remember some type of way to reencode the mp3's in Windows on the fly to fit more on the tiny storage. I think Apple getting their connection into aftermarket car radios at the time was a big factor in a universal standard which made having an iPod almost necessary for people driving. My standout MP3 players were the Diamond Rio and Creative Muvo 4GB. The smaller iPod mini was really nice for running though.