So I've been fooling around with some old MP3 players lately and it really makes you appreciate all the amenities we have in more modern media players like VLC.
WinPlay3 is the first realtime MP3 player ever created, developed by the Fraunhoufer Society, the same institute that developed the MP3 format itself. The version I've been experimenting with is the latest release 2.3b5. It's about as bare bones as you can get; you can play, pause and stop a song, skip between them, and put your songs/playlists on repeat and shuffle. That's it. The seek bar is only visual (you can't actually use it to skip to certain parts of a song), there's no software volume control, no album art, no visualizations... nothing. It does have the advantage of being extremely lightweight (the entire program is less than 1 MB in size) and of course, it works. In all fairness, many 90's laptops have a hardware volume control, usually a volume wheel on the front or side of the computer so not having one in the program itself wasn't a huge deal at the time. Also, MP3 players had to start somewhere.
I've also been fooling around with Winamp 2.95 (released in 2003 IIRC but the original release of Winamp 2 dates from 1998) - when it comes to software, it doesn't get much more 90's than this player. It definitely has more features than WinPlay3 (the seek bar actually works, there's a volume control, equalizer, and Winamp can also play a limited number of video file formats) and is extremely customizable. It's undoubtedly a cutting edge piece of software for its time, but still feels dated by modern standards of course. There are a crap-ton of skins and plugins you can use - it's probably easy to make your own skins if you wanted to. I did install a plugin that adds support for album art, which doesn't work quite right most of the time - it the song name has any non-Latin letters it will refuse to display the album cover, and sometimes you have to switch to a song w/o an album cover for it to display the correct one of the current song. All these woes remind me of how far media players have come since the mid to late 90's.
Playback in VLC and other more modern media players sounds a bit cleaner than WinPlay3 and Winamp 2, although both of the latter have a distinct "90's" type background noise that's hard to explain but I like. For songs from the likes of Junko Yagami, Counting Crows and Dire Straits it actually fits really well!