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 Taylor Swift attacked at The Grammys! Taylor Swift buys $17m home... and pays in cash Fall out Boy play Killer Karaoke - covering Taylor Swift (NSFW) Become a fan of The Edge on Facebook and on Twitter .