Through all the ups and downs, including a bout with neck cancer in the '90s that effectively aged his voice several decades, Prine has enjoyed a cultish following among his better-known peers. He's the quintessential "musician's musician." Imitated frequently, name-checked often.
How better to evaluate the 63-year-old Chicago-bred singer-songwriter than with a roll call of his most famous fans? After all, the old maxim holds true for Grammy-winning folk singers, too: You can tell a lot about a guy by the company he keeps.
Roger Ebert: Supposedly, the influential Chicago Sun-Times movie critic was the first journalist to write about Prine, praising the moonlighting mailman after attending one of his early shows at the Earl of Old Town, a legendary folk-music haunt in Chicago, in the late 1960s. "He said my songs were like little movies and a lot more interesting than what they were showing down at the theaters," Prine told the Ottawa Xpress culture blog, years later.
Kris Kristofferson: Ebert wasn't the only emerging celebrity who admired Prine's pre-label performances in Chicago. After seeing Prine perform an after-hours set, the bearded "A Star is Born" crooner was practically green with envy. "Prine is so good, we'll have to break his thumbs," Kristofferson recalled saying. Rather than maiming the upstart, Kristofferson facilitated Prine's career by setting him up at Atlantic Records. Prine's self-titled debut album (1971) was a critical hit, featuring such sad, worldly tunes as "Hello in There" (about the rigors of aging) and "Far from Me" (a waltz about his unrequited love for a waitress).
Bob Dylan: Frequently compared to the folk superstar, Prine quickly made a fan of Dylan, who appeared unbidden at one of the former's first New York City club shows and anonymously backed him on harmonica. Decades later, Dylan remains effusive in his praise. "Prine's stuff is pure Proustian existentialism," the one-time Wilbury told the Huffington Post. "Midwestern mindtrips to the nth degree. All that stuff about 'Sam Stone,' the soldier junkie daddy, and 'Donald and Lydia,' where people make love from 10 miles away. Nobody but Prine could write like that."
John Belushi: Prine credits the late funnyman — an acquaintance from his Windy City days — with helping him score his first national TV appearance. "I got on SNL because of John Belushi," Prine told an interviewer in 2005. "Every time some big musical act got booked and somebody got sick or they had to cancel, Belushi would always put my name in the hat and say, 'Ya gotta get John Prine.'" It finally worked in 1976, when Prine flew up from Aruba on a moment's notice to fill in for the Beach Boys.
Johnny Cash: In his 1997 autobiography, the late Man in Black admitted he used Prine — a Grammy winner for Best Contemporary Folk Album in both 1991 (The Missing Years) and 2006 (Fair and Square) — as inspirational caffeine. "I don't listen to music much at the farm, unless I'm going into songwriting mode and looking for inspiration," Cash wrote. "Then I'll put on something by the writers I've admired and used for years. Rodney Crowell, John Prine, Guy Clark, and the late Steve Goodman are my Big Four."
Billy Bob Thornton: One of Prine's most enthusiastic late-career champions, Thornton cast the musician in his little-seen 2001 family drama Daddy and Them — fitting, given Prine's strong resemblance to the actor (except that Prine's salt-and-pepper pate is real). When Prine won Artist of the Year at the Americana Music Awards in 2005 but was unable to attend, his boy Billy Bob picked up the award in his stead.