During the course of filming the crew members felt uncomfortable with George Strait doing his own stunts during the roping scene. Strait finally convinced them to let him do his own roping for that scene, as he is a real team roper and hosts his own team roping event every year in which he and his son compete.
The voice of the little boy in the opening song is that of George Strait's son, George "Bubba' Strait Jr.
There was a scene where Harley was supposed to punch Wyatt in the face. The first time the actors attempted it with the cameras rolling, George Strait fell to the ground after Isabel Glasser threw her punch and the director called "Cut". Strait laughed and said, "I felt the wind on my nose on that one and I will never make you angry."
The band that appears in the film, with the exception of John Doe as Earl, is George Strait's real band, "The Ace-In-The-Hole Band". In the scene after Buddy lip-syncs on stage and the the band argues with Lula (Lesley Ann Warren), the three band members who prominently have lines ("If we speed up or slow down, he can't keep up!" "Buddy Jackson?" "Are you out of your mind?") have been with Strait since the beginning of his career.
The title track, "Heartland", had to be rewritten many times to fit George Strait. It was originally as a hard rock song called "Pure Country", from which the film got its title.
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