In the 1970s, Lucinda Williams was too bluesy 

 for folk. In the 1980s, she was too country for
 rock and too alternative for country. In the 1990s, it took her six tries to record two albums — and the process nearly drove her and all her confidants, band members and significant others crazy. But 1998’s Car Wheels on a Gravel Road, released when Williams was 44, represented her big break, bigger than becoming a songwriter’s songwriter, bigger than winning a Grammy for Mary Chapin Carpenter’s No. 1 rendition of her 1992 song “Passionate Kisses,” bigger than being a cult favorite with an alluringly forlorn voice that one critic described as “the kind that suggests the rise and fall of empires as witnessed through the bottom of a shot glass.”

Born in Lake Charles,
Louisiana, Williams had
an upbringing that was
aristocratic and adventurous in an academic way. Her father, Miller, was a lauded poet
(he read at Clinton’s second inauguration) and a literature professor who bounced from teaching post to teaching post all over the South and beyond. Lucinda, who started playing guitar and writing songs at age 12, got kicked out of high school and dropped out of the University of Arkansas before wood-shedding through New Orleans, Austin, San Francisco, Houston, Nashville and New York City. She performed every chance she got and recorded when and where she could; Smithsonian Folkways backed her first two albums, a collection of country and blues covers and a hesitant collection of originals called Happy Woman Blues

Nothing in her future discography would ever be so obviously positive again. In the mid-’80s, CBS Records in Los Angeles famously paid for a demo and said it was too country before sending it to its Nashville division, which found it was too alternative. Further struggles ensued; UK label Rough Trade backed her 1988 self-titled breakout, but commercial success didn’t accompany critical success. RCA Records president Bob Buziak signed her immediately thereafter; Buziak got canned, though, and the creation of 1992’s Sweet Old World morphed into an exercise in near-futility, taking three tries to get right.

Sung in Williams’ gravelly, homespun soprano, lead single “Passionate Kisses” received modest attention, selling 100,000 copies. But when Carpenter put a honey-dipped spin on it, the song rocketed up the charts, earning Williams a reputation as an in-demand songstress. 

Still, solo success eluded her. It wasn’t until 1998’s Car Wheels on a Gravel Road that Williams finally figured out how to meld her mournful roots-rock, fiery electric blues and slacker alt-country into a cohesive whole. But that album was even harder to finish than Sweet Old World. She recorded 13 songs for it three different times over six years. Each time, she was notorious for walking out of sessions, flying collaborators in from all over the world to record and then scrapping their contributions, and forgetting lyrics in mid-take she’d sung hundreds of times. 

“I’m trying to keep the edge on,” she explained to the New York Times in 1997. 

And keep it she did. Williams struck an impressive balance between hangdog despair, sexual loneliness and kick-ass independence throughout the now-classic material. 

Between 2001 and 2011, Williams finally got over her dislike of recording, releasing twice as many albums in those 10 years as she did in the previous 20. She won another Grammy in 2001 for “Get Right with God” and was named the best songwriter in America by Time in 2002. Today, Williams is a bona fide hero of the music business: a no-nonsense woman who does things her own way at her own pace. Her current tour is a victory lap for the 25th anniversary of her self-titled debut album. 

Life for Lucinda Williams has turned out pretty well. A grueling tour schedule for the last 40 years has helped her beat spinal bifida. A lifetime of doomed love was conquered when she married music executive and manager Tom Overby in 2009. And, past age 60, she hasn’t given up on life as a hell-raising nomad. 

As she told The New Yorker in 2009, “They’re always saying, ‘You must be glad to get back to your own bed again.’ Well, depends on how you look at it. First of all, I need a new bed. I’m still restless as hell.”