When Shelby Lynne took the stage in 2001 to accept her Grammy for Best New Artist, she seemed as baffled as anyone. “Thank you very much,” she told the audience. “Thirteen years and six albums to get here.” I Am Shelby Lynne — initially released 20 years ago today in the UK — was her breakout album, but she had by then spent nearly half her life as a recording artist in Nashville. The Alabama native hit town as a teenager and was signed almost immediately. Her first release was a 1988 duet with George Jones called “If I Could Bottle This Up,” and she later worked with legendary producer Billy Sherrill (Tammy Wynette, Charlie Rich, Johnny Cash, pretty much everybody else in Tennessee). That should have been enough to make her a young star, something similar to what LeAnn Rimes or Taylor Swift would later become.

But Nashville loves its legends in the Hall Of Fame, not in the recording studio, and Lynne’s coronation by the city’s superstars may have done more to hurt than to help her. She struggled through the 1990s to live up that initial hype, to make a name for herself among popular hat acts like Garth Brooks and Allan Jackson, who were taking over the city and leading radio away from traditional country sounds. Each new Lynne album garnered fewer sales, fewer singles, less attention. Eventually, her major label cut her loose, and the former phenom could barely get arrested in Nashville anymore.

But that’s only the first volume in Shelby Lynne’s long (and ongoing) rags-to-riches-to-rags-to-riches story. With nothing to lose, she fled Nashville and moved out to California. Why not? Instead of collaborating with another country producer, she called up Bill Bottrell, then famous for helming albums for Michael Jackson, Sheryl Crow, and Madonna — a pop producer, in other words. Before they even entered the studio together, he encouraged her to expand her songwriting, to write more personally about herself and her own life. As Lynne told the Los Angeles Times on the eve of the album’s 2014 reissue, she “didn’t even know how to write” songs before she started working on I Am Shelby Lynne.

Feeling freed from the structures of mainstream country — even mainstream country that called itself traditional — Lynne made an album that boldly mixed country and soul, that treated R&B and C&W as essentially the same thing. She cited Al Green and Dusty Springfield as influences, alongside the innovations of Bobbie Gentry and the grit of Otis Redding and the breezy heartache of Stevie Wonder, as though they were all coming from the same musical tradition. The instruments on I Am Shelby Lynne are so well deployed that you can go 20 years without realizing just how small the crew was: just her and Bottrell and a few other players, all trading off instruments. You could go another 20 years without realizing how dependent these songs are on drum loops, which are so deeply absorbed into the mix that they sound live. Nothing here sounds trendy, but nothing sounds revivalist either, not the ’60s pop strings on “Black Light Blue” and certainly not the percolating jazz flute on the sublimely breezy “Dreamsome.”

Thought it wouldn’t be given a US release until January 2000, I Am Shelby Lynne effectively re-stamped Lynne as a brand new artist. Opener “Your Lies” dares you not to listen, introducing her with an en medias res blast of strings and percussion: a big, blustery, dramatic fanfare, as much punk as old-school pop and certainly not country, and one of the great overtures of the 1990s. “Your Lies” is a breakup song, ostensibly romantic, but you have to wonder if she wasn’t singing those lyrics to the music industry that had fumbled her first career and stifled her young dreams. “I got those bills you would not pay!” she declares, drawing out every word for maximum recrimination. She makes the song a professional fuck-you-very-much as well as a romantic j’accuse.

As much credit as Lynne gets for reminding listeners that country and R&B are drawn from the same deep well, she is often overlooked as a witty songwriter, one who can locate a kernel of humor or outrage even in the saddest line. Fashioning a song around a vague phrase like “life is bad” shouldn’t work as well as it does on “Life Is Bad,” but she makes that understatement sound like some kind of cosmic joke. Writing about her Alabama home, she opens “Where I’m From” by erasing any romantic notions about the South: “Heaven knows this ain’t no Margaret Mitchell.” Then she ends with the admission, “I’m high as the tide.”

And 20 years on, my favorite lyric might be this seemingly tossed-off line from “Thought It Would Be Easier”: “I found that old shirt you used to wear, and it really brought me down.” It’s such a perfect country couplet, modest and low key, yet she sings it so off-handedly and savors that outdated slang that you realize there’s some joy in her sadness, some sense that this pain grants her membership to that large community of people who have ached in pop songs.

People may have been baffled by Lynne’s Grammy — and even today her win is regularly included in listicles enumerating the award show’s most egregious mistakes — but in retrospect, maybe the Grammys were treating the Best New Artist category as maybe not as literal as it had been in years past. Lynne was by then an industry veteran in exile, but she had managed to reinvent herself so dramatically and so fundamentally that she essentially made herself new. Such was the power of I Am Shelby Lynne that it essentially erased everything she had been before, and the Grammys acknowledged that she had managed to accomplish something even more remarkable than making a strong debut album: She had made an even stronger second debut album.

“To me she’s as good as Billie Holiday, but I knew she was going to have trouble being commercially successful in Nashville,” Willie Nelson told Spin in 2000. “They don’t know what to do with someone that talented.” Maybe they still don’t. I Am Shelby Lynne sounds starkly, almost depressingly prescient in 2019, when women are routinely blocked from mainstream country radio. Women artists still can’t thrive singing straight country, so crossover appeal becomes all the more important, whether it’s toward the pop crowd (Taylor Swift), the indie crowd (Kacey Musgraves), or the roots crowd (pretty much everybody else). Lynne forged a path not so that others would follow her, but so they could forge their own.