It’s been 59 years since he wrote his first song at age 11, but despite that precociousness, Kris Kristofferson, star of song and screen, was a mere janitor when he turned 30. Of course, he was probably the only janitor in the world who had completed a Masters in English at Oxford on a Rhodes scholarship and had also been an Air Force captain.

It’s been a long, strange road for the Brownsville, Texas native. He lived up to his childhood nickname (Straight Arrow), becoming a Golden Gloves boxer while attending Pomona College in California and then following in his father’s footsteps into a U.S. air force career.

But, while he was in England falling in love with the poetry of William Blake, he was snagged by impresario Larry Parnes. Parnes managed icons of the early 1960s like Tommy Steele and Johnny Gentle, but turned down a contract with The Silver Beatles, who later dropped a word from their name and became the biggest pop band in musical history. Kristofferson recorded some tracks under the name of Kris Carson, but the tapes came to nothing due to legal issues.

So, he returned to the States, married Fran Bier in 1960 and had a kid. He was teaching at West Point in 1965 when he ditched out for Nashville instead, becoming a caretaker at CBS Studios. On the other side of his broom he watched Bob Dylan record Blonde on Blonde, but knew he would be fired if he approached the songwriter. He did, however, give all of his songs to another singer named Johnny Cash. Again, nothing came of this.

In a 2005 interview with ABC’s Andrew Denton, Kristofferson confirmed his regret for one of the most amazing actions of his life. During a stint with the National Guard in Tennessee, he landed a helicopter on Cash’s lawn, stepped out and handed him some demos. “It was a huge invasion of privacy,” he said. However, Cash ended up recording “Sunday Morning Coming Down,” which became a hit and the Country Music Association’s Song of the Year for 1970, and a long friendship between the men was formed. Ray Stevens also had a hit with the song. Soon, Jerry Lee Lewis, Bobby Bare, Waylon Jennings and others were lining up to record Kristofferson originals.

Hanging in Nashville had its drawbacks, however, as Kristofferson was imbibing about a bottle-and-a-half of Jack Daniels a day when a pregnant Fran left him. His family also disowned him.

The songwriter embarked on an intense affair with Janis Joplin, hoping she would record his song “Me and Bobby McGee.” When he first heard her version after her death, he broke down and cried. It became her only number one single. Roger Miller also had a hit with the song in 1969, having begun recording it even before the songwriter finished writing it. It seemed the hard living and years of studying gifted poets were paying off. He once said, “Never go to bed with anyone crazier than yourself,” and then added, “You’ll break that rule and regret it.” Years later, he answered “No” when questioned as to whether Joplin had been crazier than he was.

His 1970 marriage to singer and actress Rita Coolidge begat another child and three albums as a couple until their 1979 divorce, while his Kristofferson (1970) (re-released a year later as Me and Bobby McGee), The Silver Tongued Devil and I (1971), Border Lord (1972) and Jesus was a Capricorn (1972) could do no wrong. In the meantime, he began to appear in movies like Alice Doesn’t Live Here Anymore and Sam Pekinpah’s Pat Garrett and Billy the Kid.

He won a Golden Globe for A Star is Born with Barbra Streisand. While watching a clip of the 1976 film nearly 30 years later, he quipped, “She’s a mighty good sport to sing with somebody that sings like me,” just before admitting that she had been a 10 out of 10 on a scale of difficulty to work with. A 1979 role in the ill-fated Heaven’s Gate, which bankrupted United Artists studios, seemed to dim the actor’s star for a while and signalled the start of tough times career-wise. (For Kristofferson’s incredible revelations to Andrew Denton about the political assassination of the film by Washington, see abc.net.au/tv/enoughrope/transcripts/s1422317.htm)

While his film career had taken off, his albums began to crash – starting with his fifth, Spooky Lady’s Sideshow in 1975. Although he was inducted into the Songwriters Hall of Fame in 1985, both careers got caught in the crossfire after he travelled to Central America and spoke out about the United States’ “bullying” of the Nicaraguan government.

Kristofferson and third wife, Lisa Meyers, went so far as to adopt the two daughters of a slain El Salvadorian woman, Maria, who had been a nanny for him during his single-father-on-the-road years. He and Meyers, whom he married in 1983, also live with five children of their own at their secluded Maui home, which he says is why he has been on the road less frequently during the last decade.

His political statements didn’t help his career as it plummeted from stadium shows back to honky-tonks. While its nadir may have occurred when he appeared in the movie Big-Top Pee Wee in the 1980s, a bright spot arose. He joined Cash, Jennings and Willie Nelson (now his Maui neighbour) to form The Highwaymen in the mid-’80s. The group released several successful albums and Kristofferson told a CBS reporter, “I always looked up to them all, and felt like I was kind of a little kid who had climbed up on Mount Rushmore and stuck his face out there.”

His star settled in again in the 1990s. He appeared in the critically-acclaimed European movie A Soldier’s Daughter Never Cries (1998). He was a wild half-vampire character as Whistler in the Blade trilogy, creating a fresh legion of fans to join those who had loved him since 1970. After elective heart bypass surgery in 1999, he was also in Tim Burton’s remake of Planet of the Apes. He became a member of the Country Music Hall of Fame in 2004.

After three marriages, 10 children, about two dozen albums and more than 80 films, This Old Road, his 2006 album, is straight-up and breezy, but not afraid to look bullshit in the eye. In contrast to the last couple of Johnny Cash albums, which felt like the singer was saying goodbye, Kristofferson sounds like he’s got decades of spit and fight left in him. While he’s unafraid of referencing the past, he is still raging against the political cuckolding of the American public while spinning songs of perspective, gratitude and love.

No wonder the smart, sexy ol’ grandpa is the draw at this year’s folk festival. It’s not because of what, or who, he’s done, but because of who he still is.