[2][3] An IFBB Pro League bodybuilder, Cutler is a four-time Mr. Olympia winner, having won in 2006, 2007, 2009, and 2010; and a six-time runner-up, the most in history.

He grew up in nearby Sterling and attended Wachusett Regional High School in Holden.

He graduated from Quinsigamond Community College in 1993 with a degree in criminal justice, intending to work as a corrections officer for a maximum security prison.

As he established a name for himself in the bodybuilding scene, he often appeared in bodybuilding-related videos including Battle for the Olympia 2001, a pre-contest documentary video directed by Mitsuru Okabe that highlighted many competitors as they prepared for the 2001 Mr. Olympia Competition.

At the 2001 Mr. Olympia, Cutler tested positive for banned diuretics,[8] but sued and had his second-place finish reinstated.

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.