so I'm not sure why it's doing this, but I have in my cdlc folder a Hollywood undead song and a staind song which both are called Outside. If I go to staind's song outside the artwork and song for Hollywood undeads version will show up and then cause my game to be unresponsive. Just curious if there's any particular reason it would do this? I'm pretty sure I have other songs in there with the same name by different artists and it's never caused this issue before.

That is most likely because the DLC name is the same. If you open the toolkit and import them you'll see that the dlc name is the same for both.

Best way to fix it is to let the charter know.
Or rename that field for one of the songs.