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So maybe a certain media player has this capability? I'm setting this up for a friend, and although I myself am a Linux user, he mostly uses Windows, so it would be preferred if this could work for Windows.

I think it could be done using playlists. The idea is that I can make a playlist with some playlist-capable media player, then have it somehow start off exactly where it was when it stopped playing last with a bookmark. I know some mp3 players can easily do this, but on the computer, it's a different story, and I'm not sure how it can be accomplished.

Any suggestions would be greatly appreciated!

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Do you just mean start at the same/next track or EXACTLY where it left off? Most media players will remember where in a playlist you were... –  Shinrai Oct 27 '10 at 16:57
I mean exactly where it left off. The same track, and the same moment within the track. –  Hassan Oct 28 '10 at 17:49
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up vote 0 down vote accepted

JetAudio keeps file history similarly to the undo button.

I don't know about bookmarks, but when it re-opens, the track starts at the same timestamp it was at when the app last closed.

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