Sony's Walkman MP3 players come with one particularly inconvenient feature—you can only delete files from the Walkman by using a program on your computer. The downside of this is that if you want to free up space on your MP3 player to make room for a song from a friend, you can't do it unless you have your computer with you. The upside is that you can't accidentally delete a song from the player while you're on the go. Microsoft's Windows Media Player even makes the process fairly simple.
Step 1
Connect your Walkman to your computer. Open Windows Media Player.
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Step 2
Click on the "Switch to Library" button in the upper righthand corner of the screen, if the "Now Playing" view is visible.
Step 3
Find your device in the list of connected devices on the left side of the screen. Click the arrow next to your device.
Step 4
Click the type of media (music, video, etc.) you want to delete. In the middle "Details" pane, right-click on the song or video you want to get rid of, then click "Delete."