Like movies, some music and music videos are so bad that they're awesome and hilarious. Intentionally bad counts. Unintentionally bad is even better for the schadenfreude aspect.
Here are some of my favorites.
Fry That Chicken!
This is a hit-or-miss for some folks. Warning, possible racism trigger.... highly probable insanity trigger.
Lubelski Full
This is just so bad that it's kind of embarrassing and painful to behold. That poor woman. That poor guitar guy. My poor ears!
Jesus is My Friend (Sonseed)
This one is probably the most well-done musically of what I'm posting. However, still hilarious.
Indian Thriller
It's hard to top Bollywood remakes of Michael Jackson.
