Bob Dylan

Bob Dylan is a gifted songwriter, there's no doubt about that. He also paved the way for other grassroots musicians that followed in his footsteps. However, his vocals are downright awful. They always were and they only got worse with age. 

Taylor Swift

Taylor Swift is pop's biggest success story, and she likely always will be. With countless hit studio albums under her belt and no signs of stopping, she's enamored fans for over a decade. However, her vocal work can be a little shaky at times.