Hmmm...I don't actually understand either of these.  

What do you mean by "waiting"?

When do they show this status? Is it when you try to play the songs or when you try to sync them to your device?

Where does this "status" show up?

It would be natural to say:

When I try to ___________, the songs refuse to _______, and the part of the screen where _______, shows "waiting".

In regards to the actual structure of your sentences, not taking into account my confusion, it should look like:

"All of my songs in itunes are showing a 'waiting' status"

"All of my songs in itunes are shown as 'waiting'"

Even if you say this though, most people would just ask you the same questions I did up top.

Give me more details and I will try to explain more fully.

All my songs in iTunes are shown as "waiting" status. seems more naturally :)