Natalie McIntyre grew up scared to speak. The daughter of a schoolteacher mother and a steel worker stepfather, she was teased throughout her childhood in Canton, Ohio, for her funny voice—a rasp that, no matter how she tried, squeaked like a dog toy. So she retreated into herself, making up songs and thinking of a different life. She didn’t learn to hold a conversation until she was 10 years old. But she was always dreaming. As she tells it, when she was 6 she fell off her bike and landed next to a mailbox. Looking up in a daze, she read the name Macy Gray. Or maybe there was no bike accident, and the name came from a friend’s father. It’s not important. Either way, as one story goes, Macy Gray soon became a new identity, someone who wrote stories and songs—someone who, Natalie imagined, people would listen to. (It’s beside the point that the real Macy Gray was an old man who, once Natalie adopted his name as her own, would later attempt to extort her.)

Natalie was undeniably gifted, having begun classical piano at age 7; a loner in high school, she read Angela Davis and watched movies by John Cassavetes. After graduating high school she moved to Los Angeles to study screenwriting at USC. Her early musical career was a series of false starts: Surprised that the great embarrassment of her youth could be considered a gift, she wrote songs with friends, filled in vocals on demos and sang in jazz clubs, her voice not yet a superpower but no longer a liability. Now officially embodying the persona of Macy Gray, she partied hard, played any open mic or gig offered to her in hotel lobbies or on the Sunset Strip, and fell in with a group of musicians. She helped run a club called the Wee Ours where Mos Def and the Roots hung out. She sent her demos to labels and worked random jobs. She idolized Billie Holiday, but, as she later told The New Yorker, for all the wrong reasons: “I wanted to die young and go on drugs and all that shit.” She met a mercurial mortgage broker named Tracy Hinds and fell in love.

In 1994, an A&R from Atlantic heard the 25-year-old Gray play at the Roxy and signed her. The next part depends on who tells it: whether it was because she got pregnant or because the A&R left the company, Atlantic dropped Gray and shelved her debut, a traditional rock album called A Thing of Beauty. Three years later—reeling from a disastrous divorce from Hinds—she gave up hopes of making it and shuffled back to Canton to live with her mother and three children. Then the call came. Jeff Blue, the A&R from Zomba Music Publishing responsible for discovering Limp Bizkit and Korn (your guess is as good as mine), had heard her demo and, floored by Gray’s voice, wouldn’t stop calling until he convinced her to give a career in music another shot. With a family to feed and a lingering desire to keep performing, she gave in—someone, for some reason, wanted to hear what she had to say. It was the last time she’d live in Ohio.

Blue was canny. He knew labels would be scared off by Gray’s flame-out first attempt, but he banked on them being unable to deny her voice. So he sent a new demo to every major, changing Gray’s name to “Mushroom” to obscure her identity. She ended up with a generous record deal from Epic and the backing of a gimlet-eyed A&R named Andrew Slater. Two years earlier, Slater had discovered Fiona Apple and produced the entirety of her debut album, Tidal, and Epic hoped he could recreate that magic.

It worked. Released in the summer of 1999 (if you couldn’t tell by the brooding, windswept Y2K cover art), and written entirely by Gray, On How Life Is is a 10-song embrace of uncontainable warmth and honest reflection, the debut album that only a 31-year-old mother of three could create. This is music for adults: Gray’s songs sweat and cry and mourn, fuck and regret, praise God and even plot murder. They’re sung confidently and with hunger, but never with desperation; when things feel irredeemable, like on the sprawling I-still-love-you ballad “Still,” Gray nonetheless makes it clear she’s OK—or if not totally OK, at least at peace. She sings with the knowledge that life goes on, and this sense of having lived it for real is its own form of profundity, a knowing, even parental, version of the 18-year-old Apple’s world-weary jaggedness. If Gray’s radical acceptance and playfulness removes the raw intensity that made Apple’s Tidal an immediate sensation, it replaces it with something less marketable, but no less powerful: There is so, so much life to live.

Nowhere is that grateful perspective clearer than on the ecstatic gospel funk of “I Can’t Wait to Meetchu,” in which Gray takes the idea of meeting God in the afterlife to a fanatical extreme: “Love the life I’m livin’ though, I’m looking forward to the day I die,” she sings airily. “Oh my Lord, I can’t wait to meetchu.” The concept is a bit of a shocker—it’s one thing to be grateful for life, but to be excited to die? Then you hear how Gray sings it; she sounds like she’s smiling. And as the electric organ and horns build, and the drums get a little more raucous, and as her straight-shooting background singers push ahead, all of it culminating in a nearly two-minute instrumental jam session, you understand she’s singing not just about God but about hope in the face of disappointment, that “natural fact” of believing, as she tells us, “the one who’s always by my side.” The album’s final song, “The Letter,” doubles down on that fatalism, with an escapist twist calling back to the days Natalie McIntyre dreamt of being somewhere else: “So long everybody!” Gray sings gleefully on the chorus. “Life was a heartache and now I am finally free.”

“I Can’t Wait to Meetchu” is one of several unexpected genre experiments on On How Life Is, an album that skips across moody hip-hop and thick funk, syncopated R&B and piano-driven alt rock, samba and reggae and jam band eclecticism. It sounds like a lot of things at once, which was a problem upon its release, particularly in 1999. That year’s best-selling album was the Backstreet Boys’ Millennium, and TLC and Britney Spears battled for dominance on the Billboard charts; less anticipated successes that year for maturer artists like Carlos Santana, Maxwell, and Sarah McLachlan nonetheless still fit naturally into established genres. So it wasn’t entirely surprising that, despite rave reviews and Epic’s careful rollout, On How Life Is sold only 20,000 copies its first two weeks, not taking off until its second single, “I Try,” broke through three months after the album’s release. (The label’s PR campaign ingeniously began with Gray’s voice singing anonymously across a 1998 Gap ad, leading to widespread speculation as to her identity. “WHOSE VOICE WAS THAT, ANYWAY?” a giddy Washington Post headline asked when it was finally revealed.)

Initially the album was categorized as neo-soul—lazy but inevitable coming on the heels of two of the most impactful debuts of the entire decade in 1997’s Baduizm and 1998’s The Miseducation of Lauryn Hill. Gray’s debut shares little in common with those albums—the record’s original title, Macy Gray on How Life Is, was wisely ditched—outside of a virtuoso Black woman at the center; she’s downright silly compared to the somber wisdom of Badu and the lush introspection of Hill. Her storytelling influences are far more sprawling: the confessional songwriting of Apple, Tracy Chapman, and Aimee Mann, the cathartic, stadium-rocking torch songs of Elton John, the come-together bandleader vibes of Sly Stone. All of it held together with a voice that The New Yorker, in its 1999 profile of Gray, wryly compared to “Nina Simone… Rod Stewart (on helium) and Louis Armstrong.”

It’s a voice textured like steel wool, scratchy and worn, prone toward jazzy howls and spat-out asides delivered with laughter. But it’s also elastic enough to convey emotion with shocking precision. Just listen how it builds alongside the slowly brewing force of “I Try”; Gray’s voice is as distinct at a humbled stage whisper as it is on the final chorus, when she’s screaming send-offs and modulating a key or two. She speak-sings over the marimba and steel drums of “I’ve Committed Murder,” but also stretches words into smoke on the moody, Outkast– and Goodie Mob-sampling “Do Something,” pinging from animated and impassioned to disaffected and demure within a single chorus. This is the weapon Andrew Slater was working with, and he managed to organize a sound that neither over-emphasized Gray’s peculiarity or hid her profound power. He also had the help of an assemblage of session all-stars whose combined musicianship gave Gray’s voice the runway it deserved. Slater’s team included onetime Red Hot Chili Peppers guitarist Arik Marshall and the prolific percussionists Lenny Castro and Matt Chamberlain (the latter of whom played drums on Tidal), as well as the multi-instrumentalist and songwriter Daryl Swann, bassist Greg Richling of the Wallflowers and his then-bandmate Rami Jaffee, later of the Foo Fighters, and guitarist Blackbyrd McKnight of Parliament–Funkadelic. Jon Brion—Tidal’s main instrumental contributor and Apple’s future creative partner—has credits on eight of On How Life Is’ 10 songs, playing synths, guitar, marimba, and an electronic keyboard called the Optigan. A group of background singers, men and women both, act as a Greek chorus throughout.

The musicianship is spiritually maximalist. Avenue-wide choruses and whiplash chord changes flood the senses, essentially demanding these songs be performed live. It’s the ideal accompaniment for a singer who already sounded like a veteran, and whose concerns were less about how she was received by the world and more about the state of her soul. Gray told several interviewers at the time of On How Life Is’ release that if she did succeed as big as Epic hoped she would, she’d record the four albums she was contracted for and then move to France with her children—a remarkable stance for a marquee act in the twilight of the top-down major label era.

That casual indifference flows through the album, but so do love and sex. Outside of “I Try,” it’s a distinctly grown approach. “Caligula,” easily the horniest song here, is pure sex, a shuffling, drunken groove of hand-claps and languid electronic organ. It’s not so much love at first sight—Gray had already had that—as it is a match finally met. “I could not believe it/Hey, what’s your name!” she calls on the chorus, cymbals and snares alternately crashing and retreating in a barely contained storm. “Never lovin’, we’re always fuckin’,” Gray groans later, squeezing the juice out of the vowels. There’s no pursuit, just the sweaty, drunken desire of real lust, a feeling echoed on the summer-of-love-dripping “Sex-o-matic Venus Freak,” a celebration of a partner who brings out Gray’s best, porn-star self in bed, whipped cream included.

And then there’s “I Try,” which has defined Gray’s career since the moment it was pushed as the album’s second single. It’s an eternal last-call anthem, a gather-around-the-piano torch song for the ages, a once and future classic that continues to work. And for that reason it’s also far and away the album’s most calculated attempt at reaching for something easily identifiable and contemporary: in Epic’s eyes, probably the palatable earnestness of late-’90s hits like Everlast’s “What It’s Like” or Deborah Cox’s “Nobody’s Supposed to be Here.” Trading in On How Life Is’ rich musicality for a stripped-down bass, drum, and piano trio (with some strings sprinkled in), “I Try” also dilutes Gray’s lyrical zaniness, those small details and big lessons, the sex and loss and eccentricity, into a story of unreciprocated crushing and universal longing. As it often goes with The Big Song, “I Try” is in many ways the least Gray song here, the closest thing to a concession. Nothing else on On How Life Is is as rudimentary as its chorus, and nowhere else does Gray’s emotional state feel so two-dimensional. Yet its great irony is that for all of its familiarity, “I Try” is also the closest the album comes to an origin story, a true reflection of Gray’s innermost self: This is a song, literally, about wanting to talk and not knowing how, of keeping the most powerful fantasies only for yourself, despite wanting to share them with the world. And when she finally gets those words out, she lands on nothing short of how life really is: a choice and commitment, a series of mistakes and redemptions, something, above all, worth living for.