Who is Hollywood’s highest paid woman? Wed-03-Oct-12 10:34 Share this By Jay-Jay FeeneyOPRAH WINFREY is still Hollywood's highest paid woman. She earned $165 million between May 2011 and May 2012.Britney Spears is at number two, with $58 million and Taylor Swift is in third place with $57 million. You May Also Like Who did Taylor Swift lose her virginity to? Taylor Swift attacked at The Grammys! Taylor Swift's $100,000 birthday present Become a fan of The Edge on Facebook and on Twitter .