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Okay, fist, you need to make sure the player is good (boots up, goes to menu, etc.). next, you need to put all of the songs into media player, then SYNCH them to the player. If you can't do that, try putting all of the songs into a folder called "music" and then put them into a subfolder called "albums." it should work shortly afterwards.
You have songs that may be protected or the wrong format for your device. delete the bad song and download another copy from a different source and try it. This is not to uncommon due to different file formats and protection in the song files When you rip songs from another device often some won't load or play in another device especially if they are paid for songs.
To get the basics out of the way, is the volume turned up and not muted at all... if it's turned up then try another pair of headphones that you know work in something else or test these headphones in something else...( cd player, radio etc.) use a pair that you know work to retest your mp3. plug them in, turn it on and play a song the gently wiggle the end plugged into the player back and forth. If you hear a crackling or snippets of song, then it's probably the jack inside the player....try these things and get back. PS. post the make and model of your player, it helps with problem identification
The Sansa player will only recognize certain file formats. The songs with a Red X are not eligible to be transferred to your player, because their DRM license does not allow transfer to certain (or any) mp3 players.
It is best to use songs that are in mp3 format only. They will give you fewer headaches.
That player is only capable of playing songs that are in certain formats. iTunes/AAC format is out of the question. The songs that you are trying to load are probably DRM-encrypted WMA's that don't have transfer rights. Either buy the transfer rights, or better yet - only download songs that are in pure mp3 format - they will never give you grief.