My itunes songs won't play on my iphone?

A week ago, i was going to a concert. I put new music on my phone so i could listen to it in class.
The next day, i realized the songs didn't sync. I shook it off.
That night Since i have only an 8gb phone i decided i would just unsync my songs then put them back on after i took pictures and put them on my computer.
I somehow accidentally deleted the Purchased playlist on my iphone. I was getting frustrated so i just decided i would use the space i had instead of causing a hassle. So i googled how to recreate the purchased playlist. I followed the steps and got the playlist back.

When i get home a few days later, i try to sync the songs i had originally downloaded that i had in a playlist.
But they DIDN't SYNC! They wouldnt. And then some of my music (Music i bought off itunes and one or two i didn't buy i just downloaded) wouldnt play! It had a stop sign next to it, and would just skip if i tried to play them.
I restored my iphone and everything, I still can't sync the songs i wanted to in the first place. I can't sync anything.
I can't even unsync my songs?! My itunes says its syncing but nothing changes.
WHAT THE HECK HAPPENED

Added (1). i have everything updated. Its already up to date

There must have been some software problem.So, it would be better if you update your iphone softwares.

  • Why won't songs play good on my iPhone 5 but play normal on iTunes? When I download music and import it to iTunes, They play fine and normal but as soon as i put them on my iPhone they sound scratchy or like if they were getting fast forwarded. I don't think it's my iPhone because I've put songs in it before but this just started happening today. What's the problem, How do i fix this?
  • Why won't iTunes let me play songs before I purchase them? I jus started noticing this problem last night. I have an iPhone 5c. When I go into the iTunes Store and click on charts if I want to hear a song before I purchase it I click on it but it doesn't play, this does it to every song. Someone please help.
  • Songs won't play on my iPhone? I bought a bunch of songs on my iPhone 5 through the iTunes app and some of them won't play! They play on my computer but not on my phone and whenever I try to play them it just skips to the next song! Any ideas?
  • Songs won't play on iPhone 4S? So I'm having a problem with my iPhone. A couple songs out of the ones i have will not play. Some will not play at all while others while selected skip to the next song in the order. Of coarse this is happening to some of my favorite songs, so please tell me how i could fix this problem. Thanks. Also, my phone is jailbroken on IOS 5.1.1