Forget the Rio... Do you remember the MPMan?
Shortly after the MPMan’s launch, Napster came along and helped us to share and organise our music files. Transferring those files to the device was a painfully slow process over a serial connection, but it didn’t matter - music was taking its very first steps towards escaping the physical formats that it had forever been associated with.
"The MPMan was not well received," according to its Wikipedia entry. That's what you get for being first.

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i wish that people would recall the pjbox ... as far as I understand the first HD based mp3 player that was out there .. and it had a pretty cool GUI .. it had 4.7 GB and was like 780 USD back in 1999 (1998 ?) ... i still have it .. live it ... does not work that well anymore :) ... it was kinda brick sized, but it DID fit into the inner pocket of my jacket .. and it was pre-ipod ...
MPMAN F60
http://www.mferrario.it/latente/mpman-mp-f60/
the best one, my first mp3 player: id tag reader, memory expandable, radio and voice recorder. better than any ipod for me. (because has radio ;) )
@2 There are plenty of iPod competitors that include FM radio. For some reason they get made fun of for having it. Apparently no one listens to the radio anymore, at least not until Apple adds it as a feature.
@3
but no one have the style of F60
http://www.flickr.com/photos/e-coli/2526203540
:D
Please do not forget the Creative Labs Nomad Jukebox (Blue) 6GB old, old, old...
Date first available at Amazon.com: September 4, 1973
I have a bathroom scale that looks just like those things.
I had one of the black ones, it had a lovely rubberised coating, reminded me of my old zx speccy. Everyone thought it was a minidisk player, and I seem to remember that I had to leave my old P1 running all night to convert one CD to MP3s
Cant remember if I sold it, or whether is is in a box in the loft - am packing up soon, I hope I find it. Happy Memories
I had one too. I think I probably tossed it after the last move... and I remember that the interface software you needed to use to load it up with songs would only install on Windows 98 ...!
(here I am typing this on a laptop from 2002 that's still running windows 2000)
I had the 32MB MPMan F20 - one of the first on the market here in the UK, too.
I keep finding it in my stash of old electronics every couple of years and looking at it fondly. A full bank of songs would last me an entire paper round run.
Incidentally at the time I got mocked for buying an mp3 player because all the cool kids used MiniDisc. Now who is laughing? Hahaa!
Also another point: It interfaced using the parallel port. Surely the only mp3 player to do so.
I had a Samsung Yepp e32 - circa 2000. It was bought for me by a friend who dealt in audio equipment in Asia.
I could fit almost two full CD's on there at 64kbs! I remember showing it to someone in the pub - "What's an mp3 and where do you put them in?"
Eventually I dropped it once too many times and it stopped connecting to the PC.
@1:
My translucent blue PJB has survived a HD transplant and is still going strong as the primary jukebox for car trips. And its interface has a few tricks my iPod can't match. I paid a fortune for it, but it was worth it on month-long trips with 12+ hour flights.