Cutler was inspired to enter bodybuilding by personal trainer Marcos Rodriguez. Desiring to be one of the largest competitors ever, he had his first overall win at the 1993 Iron Bodies Invitational. His first contest was the 1992 Gold's Gym Worcester Bodybuilding Championships, at which he took second place. 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. He went on to win consecutive Arnold Classic titles in 2002, 2003, and 2004, and placed second to Ronnie Coleman in the Mr. Olympia competition four times before claiming the title for the first time in 2006.