The Jayhawks: Heartbreak heroes

After 15 years of illness and ill-timing, depression and dead dogs, might the rock'n'roll dream finally be coming true for the unluckiest band on the planet?

What if you made a classic, and no one cared?" As attention-grabbing headlines go, this one – from a 1,500-word piece published in The New York Times in 2000 – is up there with the best. It was picked up and repeated a few weeks ago by Rolling Stone magazine in its review of a new CD anthology of the band at the heart of that question. And if some of their individual albums were classics, what does that make their forthcoming "greatest hits" collection?

If timing is the key to comedy, it is no less crucial to rock'n'roll. And among music's many what-ifs and what-might-have-beens, the story of the Jayhawks ranks as one of its most heartbreaking. At its centre are two men, Mark Olson and Gary Louris, who met in Minnesota in the 1980s and decided to form a band. By the time they had honed their tight-harmonied, country-rock sound enough to attract the attention of music mogul Rick Rubin (the Beastie Boys, Red Hot Chili Peppers), it was 1992 and grunge, courtesy of Kurt Cobain's Nirvana, was going global.

Never mind, though, the Jayhawks had a recording contract with Rubin's American label, a subsidiary of the Warner Bros giant, and even managed their first and only US top-20 hit with the explosive "Waiting For the Sun". Then, as American pumped millions of dollars into what would be the Jayhawks' second major-label album, the influential Entertainment Weekly magazine ran a piece questioning how "non-hit groups" (ie bands unlikely to ever shift a substantial quantity of singles), would ever again make money in a rapidly shifting marketplace. "We became poster boys for label hell," the band's bassist said later. "Major labels throw money at bands and most don't recoup. That's typical. But for some reason we had all these stories written about us and it became kind of a nightmare."

Things would get worse. Immediately following the release of Tomorrow the Green Grass in 1995, Olson would quit the band and retreat to the Californian desert with his new wife, Victoria Williams. Williams, herself a singer-songwriter, had met Olson when a bunch of musicians – including Lou Reed, Pearl Jam and Evan Dando – had recorded her songs for a benefit album, Sweet Relief, the proceeds of which would pay Williams' medical bills. Newly diagnosed with multiple sclerosis, Williams became both patient and muse to Olson, whose dewy-ewed songs of desert love were no replacement for the hit-singles-that-never-were he and Louris had been writing.

The Jayhawks carried on without him. "I think that caused a rift," says Louris. "Nobody wants to feel they are replaceable and I think Mark took it personally. We didn't speak for a number of years." That "number of years" would stretch to nearly a decade. Then, in 2005, a bizarre episode would lead Williams and Olson to divorce; paving the way for a reconciliation between Olson and Louris. "I'd run over one of Victoria's dogs," Olson told me at the time. "I couldn't bring myself to tell her, so I buried it and lied to her."

Wracked with guilt, Olson drove from his Joshua Tree home back to Minnesota. While there, he also embarked on a "fling" with an ex. Williams found out and immediately filed for divorce. "She's old-fashioned about things like that," Olson told me. "You cheat on Vic and that's the end of it."

In every end a new beginning. As Olson slowly recovered and recuperated with friends in Wales, a reunion with Louris was drawing ever closer. With the Jayhawks disbanded, the pair got together to record Ready for the Flood, a gentle album of acoustic ballads, more Simon and Garfunkel than kick-ass country-rock. Of the unmistakable sound at the root of the pair's musical alchemy, Louris says: "Our voices join and it becomes this third person. We don't have vocal rehearsals. We don't chart out harmonies. I just sing and he sings, and I go where he isn't."

At one recent acoustic-duo show in London's Jazz Café, a heckler shouted: "Where's the fucking band?" Louris and Olson muttered to the crowd how under-paid and under-appreciated they felt for a band that had created a genre. That genre is alt.country, and without the Jayhawks (and Uncle Tupelo, the band that would spawn Wilco), it would never exist. It's a movement that has its own magazine, No Depression. Asked by that publication how the Jayhawks felt about the movement, bassist Marc Perlman simply replied: "We created it."

After a low-key warm-up in Spain, a couple of weeks ago the classic Jayhawks line-up took to the stage for the first time in over 13 years to play a festival back in the place where it all started, Minnesota. In the wake of the show, Louris told Billboard magazine that the band has agreed to play a few selected festivals next summer. "We'll see if it grows from there," he said reflectively.

For a band that has been on the outside looking in for so long, it's only right that its members should want to seriously manage their expectations.

'Music From the North Country: The Jayhawks Anthology' is out on Monday

The essential playlist

"Waiting For the Sun"

"Two Angels"

"Settled Down Like rain"

"Take Me With You When You Go"

"Crowded in the Wings"

"Blue"

"Bad Time"

"Trouble"

"I'm Gonna Make You Love Me"

"Stumbling Through the Dark"

"All the Right Reasons"

Get a Spotify playlist of Jayhawks songs chosen by Simmy Richman at independent.co.uk/mixtape