7 Unforgettable Photos from Kris Kristofferson’s Long and Legendary Career

It’s rare to find a star that pulls fans from wildly different places. Kris Kristofferson was one of those stars in that his fans will remember him for several things. For instance, some of his fans will remember him as one of the finest songwriters of the 20th century. Songs like “Sunday Morning Comin’ Down,” “Help Me Make It Through the Night,” and “Why Me” assured that. Some fans will remember him from his acting career. He had memorable roles in A Star Is Born, Lone Star, Convoy, the Blade trilogy, and more. Others will always remember Kristofferson as a member of the Highwaymen alongside his fellow country legends Johnny Cash, Willie Nelson, and Waylon Jennings.

Kristofferson passed away on Saturday (September 27) at the age of 88. Today, we’ll look back on his long and varied career with seven unforgettable photos.

Kris Kristofferson at Monument Records

Kris Kristofferson signed to Monument Records and released his debut album Kristofferson through the label. The photo below shows him sitting at a desk in the office. One has to wonder if the photographer knew the potential of the yet untested singer/songwriter in front of their lens.

Kristofferson and Barbara Streisand in A Star Is Born

A Star Is Born has been made four times. The first starred Janet Gaynor and Fredric March in 1937. Less than 20 years later, in 1954, Judy Garland and James Mason starred in the first remake. Then, in 1976, Kris Kristofferson and Barbara Streisand starred in what many consider the definitive version of the film. More recently, Lady Gaga and Bradley Cooper starred in the 2016 iteration of the film to great acclaim.

The press photo below hints at the insane chemistry Kristofferson and Streisand shared onscreen.

Kristofferson and Rita Coolidge

Kris Kristofferson met singer/songwriter Rita Coolidge in the early seventies. They tied the knot in 1973 and released Full Moon, the same year. They divorced after seven years, in 1980. However, their union left behind some great songs and iconic photos like the one below.

Kris Kristofferson in Rollover (1981)

Kris Kristofferson was no stranger to playing leading roles opposite some of the biggest names in show business. In the still below, taken from Rollover, Kristofferson appears with his co-star Jane Fonda.

Kristofferson and the Greatest in Freedom Road

Kris Kristofferson starred with Muhammad Ali in the 1979 made-for-TV miniseries Freedom Road. According to a statement released by his family announcing his passing, Ali sat side-stage at many of Kristofferson’s concerts.

Kris Kristofferson’s Heel Turn in Lone Star (1996)

Kris Kristofferson showed off his acting range in the 1996 modern Western film Lone Star in which he played corrupt sheriff Charlie Wade. The photo below gives a glimpse into the menacing energy of the character.

He Was a Sailor, Born Upon the Tide…

For country music fans, no memory of Kris Kristofferson stands out more than his time in The Highwaymen. The photo below shows him onstage with his fellow country icons.

Featured Image by Silver Screen Collection/Getty Images