4/11/16: From the latest iTunes version 126.96.36.199 you can no longer import the iTunes library/playlists into winamp.
12/07/14: I have uploaded a batch script that can be run to automatically clear all playlist files. Simply run the batch file each time before you open Winamp or whenever you need to clear out your old playlist files.
Playlist Cleanup Script
If your a big Winamp fan like me but are forced to use iTunes after purchasing an iPhone then this may be the solution to your problems.
I came to the point that on getting my iPhone I would now need to use iTunes for my music playback. I looked into several different options but with Winamp not being able to sync directly to the iPhone and no future development planned for it I was stuck.
I finally came up with a way but whilst this way is a bit manual I found it works as best I can to still playback audio using my favourite media player Winamp whilst just using iTunes for all the music organising and sync for my iPhone.
First off I’ll explain and guide you through what the best way I’ve found involves/doing.
Before starting this guide please make a backup of your Winamp Media Library Directory located at:(C:\Users\%YOURUSERNAME%\AppData\Roaming\Winamp\Plugins\ml\playlists)
iTunes will become your big database of music/playlists etc so if you haven’t already, export your playlists from Winamp and import them into iTunes.
[Optional] When in iTunes you should have similar options to like I have below. You can get to this page by going to “Edit > Preferences”.
The next step – Assuming you have now setup your iTunes with all your playlists and media imported into it.
Goto your Winamp media library/playlists directory.
As you can see below there are quite a few playlist files (I’ll explain why later on).
Now with Winamp closed, delete all the files ending with .m3u8 and playlists.xml.
Now start Winamp again with this folder still open and you should notice no playlists appear in Winamp anymore, but the main thing is the playlists.xml file has recreated itself with a blank configuration.
You now want to right click on the newly created playlists.xml file and goto properties and tick “Read Only” as seen below.
With this done you have setup both the iTunes and Winamp parts successfully.
Now is the part where I explain the manual tasks and what is needed by you to make this work.
The first time you start Winamp you will be greeted with a
blank media library and no playlists – This is good and will now happen each time you open Winamp.
Now all you have to do to get your media into Winamp from iTunes is goto “Library > Import iTunes Playlists”. Your Winamp should freeze momentarily whilst it imports everything, this should take a maximum of 1 minute so be patient!. You should now have all your iTunes data in Winamp to playback as you wish.
Each time you close Winamp and reopen it you will be greeted with the same blank media library window with no playlists and will have to manually click “Library > Import iTunes Playlists”. This is to ensure that if you update your media library within iTunes with new music you can successfully import it all to Winamp once you close and reopen it without duplicating playlists.
Now comes the part which involves you doing maintenance.
Each time you close Winamp the playlist files from when you last imported them from iTunes are still in the folder:
and should have similar filenames to: i_180354.m3u8. There may also be ones like: plf9040.m3u8.
New playlist files will be generated each time you import with random file names. After awhile these add up. At the present time I haven’t found an application to automate this task but once and awhile you should manually delete these files to avoid them adding up too much. I have only encountered Winamp crashing once but cannot confirm it was because of the playlist files but there were 400+ at the time.
For the last step I am sure you could write a batch file that automatically clears all playlist files with the extension “.m3u8” in that folder once a week for example. If I can find a suitable script I will update this post.