MP3 player, you turn me right round, baby...right round!

Right round through the same few songs over and over and refuse to cycle through them all! Why is that? This particular MP3 player is a 1 Gig and doesn't have a shuffle feature but I have almost 200 songs on it and it only plays a few of them then starts over playing through the same few again! I can see all the mp3 files are there when I look on the Windows Media Player, so why won't it play them all???

So frustrating. I just wanna grab my hairbrush as my imaginary microphone and rock out but I'm getting bored of the same 30 songs....anyone else have this issue and know how to fix it without erasing everything and starting over? I chose all praise and worship music for this player and handpicked/selected *just* the right songs, it would be a huge time consuming hassle to erase them all and start over. Can anybody out there help this poor girl make it work???