Craig attended R.M. Marrs junior high school. He graduated from Burke High School in 1980 and attended University of Nebraska at Kearney. Craig begin his career as a college circuit comedian in the 1980s. In 1984, he traveled the Mediterranean and Middle East as part of the USO comedy tour, where he spent two months in Turkey, Greece, Italy, Israel, Bahrain, and Spain entertaining our troops and in 1985, he was named Showtime's Funniest Person in Nebraska. Craig was nominated from the NACA Campus Entertainer of the Year award three times.