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Kristofferson's appearance in director John Sayles' film Lone Star (1996) marked a turning point in his film career. Taking a supporting role as a corrupt sheriff, the 60-year-old actor displayed a flair for character parts and villains that vastly increased his offers from Hollywood in the late '90s and led to his appearances in such major-studio action features as Fire Down Below, Blade, and Payback. He also earned admiring critical notices as a James Jones-like novelist in A Soldier's Daughter Never Cries and in another Sayles film, Limbo. By the turn of the century, complaining that he hadn't had time to tour as a singer in years, Kristofferson was looking forward to additional film work.

Although his early work was frequently repackaged and released in new compilation packages, Kristofferson released very little new work as the 21st century dawned. A live set, Broken Freedom Song, appeared in 2003 on John Prine's Oh Boy Records, and another Don Was-produced album, This Old Road, saw the light of day in 2006 on New West Records.