Jay Cutler worked in his brother's concrete construction business, Cutler Bros. Concrete, from the age of 11. He began training when he was 18 years old as a senior at
Wachusett Regional High School. 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. He was inspired to enter bodybuilding after meeting personal trainer Marcos Rodriguez. Cutler excelled in bodybuilding, desiring to be one of the largest competitors ever, and took his first overall win in 1993 at the 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 again in 2006.