Winamp was the essential party player in the 90’s. Back then there wasn’t much so-called multitasking software around for public use and this was one of rare programs so DJ’s could have two programs opened at once. This program still works today (there isn’t much support for it tho, but you can find many patched versions on-line for the sake of nostalgia – but If you are just looking for a good player – I recommend VLC), you can play any type of file format in Winamp. The whole legacy hype is because old systems and software were working good in the times that world wide web was still more of an idea and not many people used computers to listen to music and they were made with different philosophy.
Before checking compliance for newer operating systems is good the test application in virtual environment. If you plan to play with Winamp, I recommend you install it on virtual computer. Next time I will prepare quick guide how to install operating system in Virtual Box. For any questions regarded to operating system installation feel free to ask.
Windows 2000 running in Virtual box.