In 1979, Willie Nelson released a successful album of Kris Kristofferson covers, and in 1982, they teamed up with Dolly Parton and Brenda Lee to compile songs from their mid-60s catalog. In 1985, Kristofferson and Nelson joined forces with Johnny Cash and Waylon Jennings to form the supergroup, the Highwaymen. Their debut album, *Highwayman*, featuring the title track written by Jimmy Webb, brought Kristofferson back to the top of the country charts.

Throughout the 1980s, Kristofferson was an outspoken critic of U.S. President Ronald Reagan and the administration’s foreign policy in Central America, particularly its support of anti-leftist forces in El Salvador and Nicaragua. His 1986 album, *Repossessed*, touched on these political conflicts.

Kristofferson’s acting career also thrived, with a notable resurgence in 1996 when he played the villainous sheriff Charlie Wade in John Sayles' critically acclaimed neo-western *Lone Star*, alongside Chris Cooper and Matthew McConaughey. This role led to more prominent parts, including that of vampire hunter Abraham Whistler in the *Blade* trilogy, starring Wesley Snipes.


Kristofferson retired from the entertainment industry in 2021. His final film role was in the Ethan Hawke-directed drama *Blaze* (2018), and his last album, *The Cedar Creek Sessions*, was released in 2016.

He was married three times. His first marriage was to Fran Beer in 1960, followed by a marriage to singer Rita Coolidge in 1973. Their duets album, *Full Moon*, became one of Kristofferson's biggest crossover hits, reaching the Top 30 on the pop charts. They divorced in 1980. He is survived by his third wife, Lisa Meyers, whom he married in 1983, and with whom he had five children, in addition to the three children from his previous marriages.