Jeff Ross – $4 Million

Jeff Ross is an actor, stand-up comedian, and filmmaker. His brand of insult comedy and rotations around celebrity roast events earned him the nickname “Roastmaster General.” Ross made his directorial debut through Patriot Act: A Jeffrey Ross Home Movie in 2006. As an actor, Ross has featured in films like Along Came Polly and TV shows like Six Feet Under.

Ross also competed in the Celebrity Poker tournament held in 2004, and he was a contestant in Dancing with the Stars. Sadly, Ross’s reputation took a hit in 2020 over allegations of inappropriate conduct with a minor.