At the 2001 Mr. Olympia, Cutler tested positive for banned diuretics, but sued and had his second-place finish reinstated. He won the Olympia for a second consecutive year in 2007. He became the third Mr. Olympia in history (after Arnold Schwarzenegger and Franco Columbu) to win the title in non-consecutive years after defeating the reigning champion Dexter Jackson in 2009. In 2010, he won his fourth Mr. Olympia title, defeating Phil Heath. In 2011, he was runner-up to Heath at the Mr. Olympia. In 2012, he was unable to compete at the Mr. Olympia due to a bicep injury. He placed sixth in the 2013 Olympia.