Suzy Bogguss had previously worked with Riders In The Sky in 1988 when she appeared on the fifteenth episode of the Riders weekly radio series: Riders Radio Theater.
Taped on November 19th and 20th of 1990.
In the book "It's The Cowboy Way: The Amazing True Adventures of Riders In The Sky", it is mentioned that during the taping of this show, Suzy Bogguss was constantly getting phone calls from her husband, Doug Crider, because his car had broken down. As soon as the taping was over, she left to pick him up.
The first of two Christmas-themed specials Riders In The Sky hosted for The Nashville Network, the second being A Riders In The Sky Christmas in 1993.
Riders In The Sky's 1999 album Christmas The Cowboy Way is named after this special.