Kris Kristofferson did not collaborate with Nashville songwriters.
 In 1999, The Austin Sessions, was released, an album on which Kristofferson reworked some of his favorite songs with the help of artists such as Mark Knopfler, Steve Earle, and Jackson Browne
In spite of the success of Highwayman 2 in 1990, Kristofferson's solo recording career slipped significantly in the early 1990s, though he continued to record successfully with the Highwaymen

