Kristofferson died Saturday at home in Maui, Hawaii, his family announced. “We’re all so blessed for our time with him,” they said in a statement. “Thank you for loving him all these many years, and when you see a rainbow, know he’s smiling down at us all.”

 

A native of South Texas, Kristofferson starred in football and rugby and won a Golden Gloves boxing tournament while attending Pomona College in California; earned a Rhodes Scholarship to study literature abroad; and piloted helicopters in the U.S. Army.

 

He threw away a career in the military and moved to Nashville, where he worked as a janitor at Columbia Records and watched as Bob Dylan recorded his seminal 1966 album Blonde on Blonde. It took Kristofferson many months before his music career finally took hold.

 

His drifter ballad “Me and Bobby McGee” was initially recorded by Roger Miller in 1969 before Janis Joplin made it a rock classic, her throaty version topping the Billboard Hot 100 in 1971, not too long after she died of a heroin overdose.

 

Kristofferson also performed “Help Me Make It Through the Night” on his 1970 self-titled album, but it was Sammi Smith’s version that became one of the most enduring singles in the annals of country music, vaulting as high as No. 8 on the Billboard chart. 

 

Kristofferson received the best country song Grammy Award for writing “Help Me Make It Through the Night,” and he added trophies in 1973 and 1975 for his duets with then-wife Rita Coolidge on “From the Bottle to the Bottom” and “Lover Please,” respectively (he authored those tunes as well).

 

Kristofferson also wrote a morose song about a hangover, “Sunday Mornin‘ Comin‘ Down,” that was the Country Music Association’s song of the year in 1970 and a big hit for Ray Stevens and then Johnny Cash; “The Taker,” notably recorded by Waylon Jennings; “For the Good Times,” made popular by Ray Price and named song of the year by the Academy of Country Music in ’71; and “Please Don’t Tell Me How the Story Ends,” which Ronnie Milsap made his own.

 

In 1985, Kristofferson, singing and strumming his trusty Gibson guitar, teamed with buddies Cash, Jennings and Willie Nelson to form THE HIGHWAYMEN, and the four “outlaws” released three albums through 1995 and thrilled live audiences before Jennings and Cash succumbed to poor health.

 

The charismatic Kristofferson was inducted into the Songwriters Hall of Fame in 1985, entered the Country Music Hall of Fame in 2004 and was given the Grammy Lifetime Achievement Award in 2014. He received an Academy Award nomination for best score in 1985 for Alan Rudolph’s Songwriter, in which he starred as singer Blackie Buck opposite Nelson in the Nashville-set tale.

 

Starting with Dennis Hopper’s The Last Movie (1971), Kristofferson brought his manly, craggy persona to the fore in such films as Sam Peckinpah’s Pat Garrett & Billy the Kid (1973), the Michael Cimino debacle Heaven’s Gate (1980) and, as a corrupt sheriff, John Sayles’ Lone Star (1996).

 

He starred as love interests for Oscar winner Ellen Burstyn in Martin Scorsese’s Alice Doesn’t Live Here Anymore (1974), for Sarah Miles in The Sailor Who Fell From Grace With the Sea (1976) and — as alcoholic, has-been singer John Norman Howard — for Barbra Streisand in the remake of A Star Is Born (1976).