Not with the build in AutoPlaylists criteria. Not sure if an addon is able to do this.

There is a workaround in MediaMonkey if you don't have that many weight values. You can create an AutoPlaylist for each weight criteria and use Show at Most x files to limit the amount of files on each weight Playlist. Then you have an AutoPlaylist reference all these weighted AutoPlaylist to combine all the files.

For example
Weighted Playlist (rule Playlist = Playlist 1, Playlist 2, Playlist 3)
Playlist 1 (rule Weight = 1, Show at Most 100 files)
Playlist 2 (rule Weight = 2, Show at Most 75 files)
Playlist 3 (rule Weight = 3, Show at Most 50 files)

The Weight rule would be whatever field and criteria you use to define weight (could be rating, could be a Custom field). As you see your Playlist will now contain 100 files with weight 1, 75 with weight 2 and 50 with weight 3. You can either play this AutoPlaylist or feed it into Auto-DJ so it randomly selects from this playlist.

Hi,
First let me thank you for actually answering posts - how refreshing. I've had some other answered.

Here's my question (maybe a request) - I want to be able replay some mp3s more than others in a playlist as it shuffles the songs. Is there a way to indicate a "weight" for each song in the playlist, where the higher the weight, the more probable it would get replayed ?????

I am learning a language - so I have mp3s for different words/sentences..... and I want to replay the ones I am having the most problem learning more than the ones I know better. I hate to put the same mp3 file, renamed to "trick" Media Monkey in a playlist multiple times, just to get it played multiple times.

Thanks!!
VmusicV