Winamp is probably the most popular music player for Windows. I really like it, particularly version 5 of it which is much nicer to use than any of the previous versions.
But what came before Winamp? Well, surprisingly enough, DOSAmp – a music player for DOS, the precursor to Windows. It wasn’t a particularly nice program – you ran it from the command line with the file you wanted to play as the parameter. It only played back MP3s – whereas Winamp, through plugins, can play every format you can think of and many more you can’t. And it used the PlayAMP decoder so sound quality wasn’t all that hot even then. But the download was only just over 100KB, much less than Winamp or any other modern music player.
I managed to run it on this machine using DOSBox, but couldn’t get any files to actually playback without it failing. If you have a proper DOS environment you may have more success – you can download it from ReallyRareWares and see for yourself. It hasn’t been updated for the best part of 7 years and is no longer supported, but it’s a nice bit of nostalgia, I guess.
Update: For some reason, the DOSAmp screenshot isn’t showing up in my copy of Firefox (0.9.1). It appears in every other browser I’ve tried – Mozilla included – and the page validates so it would appear it’s a bug in Firefox’s rendering. Odd.
Update II: Never mind. I have some crude ad-blocking and it thought it was an advert.