Britney Spears ($215 million)
Spears has been through the wringer with public pressure, drug and alcohol addiction, unaddressed mental health issues, and career meltdowns, but she has still managed to make an absolute load of cash along the way. Spears has sold over 100 million records worldwide, making her the 8th highest-selling female artist of all time. Hit Me One More Time was Spears’ first studio album, which came out in 1999 and immediately rocketed to the top of the charts. Spears had some hiccups in her career, but for the most part, she’s kept her stream of income pretty consistent over the past 21 years.