Helly's WinAmp Control,

HWC is a program to take control of winamp and make it easier to control and manage playlists. You can easily create playlists and play them through winamp. You can create a playlist and put it on shuffle and it will shuffle through the list until you stop it. Only playing a song twice until the entire list has been played. While playing a list you can also insert a song of your choice from any other list and it will be played after the current song after which the program will return to the active playlist and continue playing the songs in it.

I personally still use this program when playing songs on my PC.

For screenshots you can check the screenshot page.