Facts about Alan Jackson music videos are that he won the 1992 and 1993 Country Music Association Music Video of the Year Awards for "Midnight in Montgomery" and "Chattahoochee." Jackson used actors from "Yes, Dear," his favorite television show, in his music video for "The Talkin' Song Repair Blues."
"Midnight in Montgomery" is about a visit with the ghost of Hank Williams, the deceased singer who was born and buried in Montgomery. The song references multiple popular songs of Williams.
The music video for “So You Don’t Have to Love Me Anymore" features Jackson on the Coney Island Boardwalk. It includes several landmarks, including the Wonder Wheel, Parachute Jump and Astrotower.
The "Yes, Dear" actors used in "The Talkin' Song Repair Blues" were Mike O' Malley and Anthony Clark. The song is about a songwriter and an automotive mechanic discussing their work with each other.
Jackson's work has received many awards and nominations over the years, and he has received awards from organizations including the Academy of Country Music, the Billboard Music Awards, the Grammy Awards, the ASCAP Awards and the Golden Boot Awards. Awards won by Jackson include Album of the Year, Single of the Year, Top Male Vocalist, Vocal Event of the Year and Entertainer of the Year.