Winamp was the essential party player in the 90’s. Still works today, you can play any type of file format in Winamp. The whole legacy hype is because old systems and software were working and they were made with different philosophy.
Before checking compliance for newer operating systems is good the test application in virtual environment. 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 Virtualbox.