In 1973, the year he and singer Rita Coolidge married, two of his albums, The Silver Tongued Devil and I and Jesus Was a Capricorn (which contained his first No. 1 hit as a singer, "Why Me"), went gold. Meanwhile his duets with Coolidge sold well and produced two Grammys for them.

Kristofferson's acting career also took off in the early 1970s, beginning with Dennis Hopper's The Last Movie. Film roles have cropped up regularly for him ever since, among them Cisco Pike, Sam Peckinpah's Pat Garrett and Billy the Kid (with James Coburn and Bob Dylan), Martin Scorsese's Alice Doesn't Live Here Anymore, The Sailor Who Fell from Grace with the Sea, A Star Is Born (with Barbra Streisand; his shirtless image on the album cover may have done his career more harm than good in the long run), Convoy, Heaven's Gate, Songwriter, and John Sayles' 1996 film Lone Star. He also contributed songs to the soundtracks of a number of these and other films. Kristofferson's last big chart success as a solo performer, in fact, was "Watch Closely Now" from the multiplatinum soundtrack to A Star Is Born. He continued to have minor chart hits into the 1980s, but nothing like his phenomenal sales of the previous decade.

In the mid-1980s Kristofferson teamed up with pals Johnny Cash, Waylon Jennings, and Willie Nelson under the name the Highwaymen, who released their first album in 1985. They've since recorded two more albums, Highwaymen II (1990) and The Road Goes on Forever (1995); the latter's title song seriously boosted the career of its author, Robert Earl Keen. Also in 1995, Kristofferson was signed onto the roster of the growing Texas label Justice, which released his first new solo album in almost a decade, A Moment of Forever.