Cutler was born in Santa Claus, Indiana, in 1983. Cutler attended Heritage Hills High School in Lincoln City, Indiana. He started three years at quarterback for the Patriots football team, amassing a combined 26–1 record in his junior and senior years, including a perfect 15–0 during his senior year. Cutler and his team outscored opponents 746–85, including a 90–0 shutout at Pike Central. During his senior year, Cutler connected on 122 of 202 passes (60. 4%) for 2,252 yards with 31 touchdowns, while rushing 65 times for 493 yards with 11 touchdowns. He also started at safety for three years, intercepting nine passes as a senior, 12th overall in the state. His team's perfect record during his senior year included the school's first 3A state championship, where Heritage Hills beat Zionsville in overtime, 27–24. The most notable play of the game occurred when Cutler lateraled the ball to the halfback, Cole Seifrig, who then passed it to Cutler who ran it into the end zone. Cutler also played strong safety in the state championship and made 19 tackles.