Cutler worked in his familys 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 Golds Gym Worcester Bodybuilding Championships, at which he took second place. He won 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 in 2006.

In 2001, at the Mr. Olympia he tested positive for banned diuretics, but sued and had his second-place finish reinstated.[verification needed] Cutler won the Olympia for a second consecutive year in 2007. Jay Cutler became the third Mr. Olympia in history (along with Arnold Schwarzenegger and Franco Columbu) to win the title in non-consecutive years, and, defeating the reigning champion Dexter Jackson in 2009, became the only Mr. Olympia in history to reclaim the title after having competed as title-holder and not won. In 2010, he won his fourth Mr. Olympia title, defeating Phil Heath. In 2011, Cutler was runner-up to Heath at the Mr. Olympia. In 2012, Cutler was unable to compete at the Mr. Olympia due to a bicep injury. Cutler competed in the 2013 Olympia and placed 6th.

Cutler has since focused on his business venture, Cutler Nutrition, which specializes in bodybuilding nutritional supplements

Cutler has been featured on the cover of several fitness magazines such, as Muscle and Fitness, Flex and Muscular Development. He currently lives in Las Vegas, Nevada.

Statistics:

• Height: 5 ft 9 in (1.75 m)

• Thighs: 76 cm (30 in)

• Calves: 51 cm (20 in)

• Arms: 60 cm (24 in)

• Waist: 91 cm (36 in)

• Chest: 147 cm (58 in)

• 1993 NPC Iron Bodies Invitational – Teenage & Mens Middleweight

• 1993 NPC Teen Nationals – Middleweight

• 1995 NPC U.S. Tournament of Champions – Mens Middleweight and Overall

• 2000 IFBB Night of Champions

• 2002 Arnold Classic

• 2003 Arnold Classic

• 2003 Ironman Pro Invitational

• 2003 San Francisco Pro Invitational

• 2003 Dutch Grand Prix

• 2003 British Grand Prix

• 2004 Arnold Classic

• 2006 Austrian Grand Prix

• 2006 Romanian Grand Prix

• 2006 Dutch Grand Prix

• 2006 Mr. Olympia

• 2007 Mr. Olympia

• 2009 Mr. Olympia

• 2010 Mr. Olympia

• 1992 Gold Gym Worcester Bodybuilding Championships – 2nd

• 1996 NPC Nationals, 2nd place Light Heavyweight (earned IFBB pro card)

• 1998 IFBB Night of Champions – 11th

• 1999 Arnold Schwarzenegger Classic – 4th

• 1999 IFBB Ironman Pro Invitational – 3rd

• 1999 Mr. Olympia – 14th

• 2000 English Grand Prix – 2nd

• 2000 Joe Weiders World Pro Cup – 2nd

• 2000 Mr. Olympia – 8th

• 2000 Mr. Olympia Rome – 2nd

• 2001 Mr. Olympia – 2nd

• 2003 Mr. Olympia – 2nd

• 2003 Russian Grand Prix – 2nd

• 2003 GNC Show of Strength – 2nd

• 2004 Mr. Olympia – 2nd

• 2005 Mr. Olympia – 2nd

• 2008 Mr. Olympia – 2nd

• 2011 Mr. Olympia – 2nd

• 2011 Sheru Classic – 2nd

• 2013 Mr. Olympia – 6th