Chrisman began playing fiddle when he was 11 years old. He played with Sam McGee and others regularly at the Grand Ole Opry in the mid-sixties. He is also extremely adept at lariat tricks. He attended Vanderbilt University in Nashville, Tennessee, and has a Ph.D. in theoretical plasma physics from MIT, where he wrote his thesis, "Inertial, Viscous, and Finite-Beta Effects in a Resistive, Time Dependent Tokamak Discharge", Thesis Nuc. Eng. 1976, PhD, supervised by James E. McCune. He returned to Nashville and began playing recording sessions and recorded and toured with Loggins & Messina.
In 1978, Chrisman approached the Riders (then consisting of just Douglas B. Green and Fred LaBour) backstage after a show and inquired about joining the group. Shortly before Chrisman approached the Riders, Williams "Bill" Collins had just left the group, so Green and LaBour were already looking for a replacement member, and Chrisman seemed like the perfect fit. Chrisman's first show with the Riders was at the 1978 Kentucky State Fair. As of 2021, Chrisman is still with the Riders.
Prior to joining the Riders, Chrisman had already written "Blue Bonnet Lady" and "Cowboy Song" (both of which would be featured on the Riders' first album, Three on the Trail). Chrisman also wrote "So Long, Saddle Pals", what many would consider the Riders' equivalent of "Happy Trails".

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