Taylor Swift

Then still a budding country singer, Taylor Swift attended her prom looking demure in a white gown. She probably had no idea how much fame and fortune the years that followed had in store for her. In 2006, her self-titled debut album landed her on the country charts and paved the way for her later mainstream success.

By the time her fifth album, 1989, came out in 2014, she was a bonafide pop star. With her record and tour sales combined, the Bad Blood singer accumulated a personal fortune worth $400 million. Lately, though, Swift has been busy and re-recording and re-releasing her past hits in 2021.