After over a half century in the public eye, doing everything from writing hit songs to appearing on the big screen, Kris Kristofferson passed away at age 88 on Sept. 28. While he may not have had the most powerful voice himself, the power of the "Sunday Mornin' Coming Down" singer's pen always ensured his songs would find the right person to guide them, with folks like Janis Joplin, Elvis Presley, Jerry Lee Lewis, Johnny Cash, Dolly Parton, Tyler Childers, and countless others recording his work through the years.
Following the unsuccessful launch of a music career under the name Kris Carson in the late 50's, Kristofferson enlisted in the U.S. Army, eventually starting a band while stationed in West Germany that revived his ambitions. Upon his return to the States in 1965, he moved to Nashville, working odd jobs to make ends meet prior to releasing his groundbreaking 1970 debut, Kristofferson. Largely written by Kristofferson himself — a format he'd continue for all 18 of his solo albums — the album produced hits like "Help Me Make It Through The Night," "Me And Bobby McGee," and "Sunday Mornin' Coming Down" and instantly made him a force to be reckoned with.
Aside from his songwriting, Kristofferson is also known for his work as an actor, most notably on 1976's A Star Is Born. Starring alongside Barbra Streisand, the romantic musical drama netted him Golden Globe Award for Best Actor the same year. Originally released in 1937, the movie's narrative has been re-hashed time and time again — including a 2018 remake with Lady Gaga and Bradley Cooper — but Kristofferson's version has continued to persist as the standard, similar to how his songs have also stood the test of time.
With three GRAMMY Awards to his name, a Lifetime Achievement Award from the Recording Academy, and a penchant for crafting hit songs that has long gone unmatched, look back on Kris Kristofferson's legacy as one of the greatest songwriters of all time.
Inspired by a quote from Frank Sinatra in Esquire magazine about what he believes in ("whatever helps me make it through the night"), "Help Me Make It Through The Night" was written by Kristofferson while staying with Dottie West as a starving artist. It's arguably the most instrumental to his success, earning him his first GRAMMY for "Best Country Song" in 1972 and inspiring covers by the likes of Sammi Smith, Elvis Presley, Johnny Cash, and Willie Nelson.
Although Smith's version of the song was the biggest commercial success (reaching No. 1 on the charts), the aching of Kristofferson's voice on the original pairs perfectly with the ballad's somber tone, leaving the listener legitimately questioning if the singer will wake to see another day.
Another of several timeless hits from Kristofferson's GRAMMY Hall Of Fame-inducted debut album, "Me And Bobby McGee" is perhaps best known for Janis Joplin's posthumous version that released and jumped to No. 1 on the Billboard Hot 100 in 1971. The song also enjoyed chart-topping success in the country community thanks to Gordon Lightfoot and Jerry Lee Lewis, further evidence of its captivating nature — and Kristofferson's prowess as a songwriter altogether.
The freewheelin', borderline waltz about two drifters hitching a ride through the American south sees Kristofferson tying together the hitchhiker's lack of anything tying them down to his own life, something best embodied in the lyric, "Freedom's just another word for nothin' left to lose."
Featuring harmonies from soon-to-be wife Rita Coolidge and fellow country/gospel star Larry Gatlin, "Why Me" sees Kristofferson pleading for spiritual guidance and direction from Jesus: "My soul's in your hand," he yearns on the chorus. It's a response of sorts to another of his most successful songs (and an eventual No. 1 country hit for Johnny Cash), "Sunday Mornin' Coming Down."
Notably, the heartbreaking hit was Kristofferson's only No. 1 on Billboard's Hot Country Songs chart as an artist in his own right. The song's success further reinforced it as one of his most enthralling and crippling compositions ever, as he questions his own good fortune with lyrics like, "What have I ever done/ To deserve even one/ Of the pleasures I've known."
Following in the footsteps of the pity-plagued lyrics of "Why Me," "From The Bottle To The Bottom" sees Kristofferson dueting with Coolidge for a combination of tongue-in-cheek humor ("If happiness is empty rooms/ And drinkin' in the afternoon/ Well I suppose I'm happy as a clam) with tear-in-your-beer heartache.
The myriad of emotions captured by the song's ambiguous title leave its interpretation constantly shapeshifting, no doubt contributing to the allure that helped it win a GRAMMY for Best Country Performance by a Duo or Group in 1974. Though the pair's marriage ended in 1980, their musical partnership proved fruitful and successful: along with releasing two more albums (1974's Breakaway and 1978's Natural Act), they celebrated another GRAMMY win in 1976 for their rendition of the Rhythm Steppers' "Lover Please" in 1976.
After more than a decade of success as both an artist and a songwriter, Kristofferson joined forces with classic country colleagues Johnny Cash, Waylon Jennings and Willie Nelson to form one of the most renowned supergroups in music history: the Highwaymen.
The iconic foursome debuted in 1985 with "Highwayman," the Jimmy Webb classic about a soul with four different incarnations that inspired the group's name. Each personification is played by a different member, with Kristofferson taking the role of a sailor killed in a shipwreck while traversing South America's Cape Horn en route to Mexico.
The success of the song and album would go on to spawn not only two more Highwaymen records in the next decade, but also inspired the formation of other supergroups like the Traveling Wilburys (Bob Dylan, George Harrison, Jeff Lynne, Roy Orbison, and Tom Petty) and Honky Tonk Angels (Loretta Lynn, Dolly Parton and Tammy Wynette). What's more, it solidified Kristofferson's place as one of country music's greats — a legacy that is sure to live on through generations to come.