Windows Media Player 9 Play Media in a Playlist in Random Order SUMMARY: Shuffle around media playback in Windows Media Player. It's simple to play the media files in your Windows Media Player playlist in a random order. Just press CONTROL-H. If you'd rather not remember this keyboard shortcut, click on the small button at the bottom of the window that looks like two arrows, one pointing up, one pointing down.   Discuss This Tip Print This Tip Get E-Mail When New Tips are Online Return to the Windows Media Player 9 page.

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