No matter what you think of her, you simply cannot leave her off this list since she was responsible for the resurgence of the teen pop star. This had been a thing in the 1980s with the likes of Tiffany and Debbie Gibson, but for almost all of the 1990s up until 1999, it had seemingly gone extinct until Spears showed up on the scene. Six of her songs have reached #1, and in 2001 and 2012 she was the highest-paid female musician. She’s got a collaboration with Elton John coming up, so don’t be surprised if that also lands at #1 in the late summer.
