“Unpopular pop.” That’s the phrase Jon Brion used in 1999 to describe the music scene at Largo, the 120-seat venue in West Hollywood where he ran a weekly residency for more than a decade. Every Friday night, seated at a secondhand piano (that at some point acquired a decorative Viking helmet) and walled in by arcane analog instruments, the star producer, composer, and musical polymath put on a show. Among frequent guests were some of Brion’s most distinguished collaborators: Fiona Apple, Rufus Wainwright, and Aimee Mann. On any given night, John Paul Jones, Jackson Browne, or even Kanye West could appear on the tiny, rug-covered stage.

Owned by Mark Flanagan, a towering Irishman with discerning taste in music, Largo became a haven for the eclectic, sophisticated pop sound Brion championed, played by performers who’d long ago outgrown open-mic nights. Flanagan also filled out bills with pillars of LA’s stand-up scene: Zach Galifianakis, Margaret Cho, Sarah Silverman. Music-loving filmmakers like Paul Thomas Anderson and Michel Gondry were in the mix, too. Largo became an ersatz salon and fostered some of the greatest collaborations of its time.

This is the environment that nurtured Mann’s brilliant 2000 album Bachelor No. 2 or, the Last Remains of the Dodo. The traditional narrative around Mann’s career frames her as an aberration. Over the course of four decades, she has been a pop flavor of the week who reinvented herself as a singer-songwriter; a folk-rock traditionalist who refused to posture her way into a self-consciously edgy alternative idiom; a woman whose persona isn’t seductive or enraged so much as pensive and, at times, embittered; an artist in a youth-obsessed industry who started doing her best work sometime in her late 30s. All of this made her an outlier in the music industry at large. But at Largo, Mann was among her people.

The gimmick-free nature of her music and public image perturbed sexist, unimaginative major-label executives in the ’90s, when the industry was still printing money and every act was expected to break out with the same velocity as Nirvana. At the beginning of that decade, Mann’s band ’Til Tuesday—a new wave act that had peaked with the breathy 1985 hit “Voices Carry”—broke up, and she launched a solo career. Her power-pop debut, 1993’s Whatever, and somewhat more muted 1995 follow-up I’m With Stupid proved she was a witty, self-possessed songwriter, even as sales in the low six figures disappointed the suits.

By the time she made her third album, Bachelor No. 2, Mann was known for clashing with the industry. In 1999, The New York Times Magazine sent reporter Jonathan van Meter to observe her struggle to get her label to release the record over their protests that it lacked a single. “A single is a record company’s job: to pick out a song that they think is good and make sure people hear it,” Mann complained. “It’s also incidentally, their job to come up with a way of selling records if, say, I don’t have a single at all.”

She wrote the deceptively winsome piano ballad “Nothing Is Good Enough” about this exhausting back-and-forth. “It doesn’t really help that you can never say what you’re looking for/But you’ll know it when you hear it,” she sings. The lightness of her vocal lends a hint of irony to her scornful lyrics, which offended her A&R rep. He assured the Times that not only had he given her specific feedback on choruses that “weren’t working,” he’d also made her a tape of better ones. Mann eventually told van Meter that she’d heard Interscope head Jimmy Iovine had listened to Bachelor No. 2 and demanded, “Aimee doesn’t expect us to put this record out as it is, does she?”

At various points during the recording process, Mann attempted to churn out the hit that would liberate her other songs from the vaults at Interscope. But she still ended up with a release steeped in the aesthetics and values of Largo, a place so hospitable to her sound that Flanagan once jokingly called it “Aimee Mann’s clubhouse.” Out of step though it might have been with a testosterone-damaged late-’90s rock marketplace dominated by Mann’s Interscope labelmates Nine Inch Nails, Limp Bizkit and Marilyn Manson (not to mention a pop sphere populated by and targeted entirely toward teens), the intricately crafted Bachelor No. 2 was a gift to the crowd Brion called “song sluts,” who lined up outside the club every Friday.

More than any album Mann had made up to that point, it’s a showcase for the detail she builds into her music before the recording process even begins. “I kind of like it to sound like a complete song before I get to the studio,” she explained to Performing Songwriter magazine in 2005. “I work hard to make sure both the melody and the words are strong before thinking about recording or production.”

The approach suits her unpretentious attitude toward music-making, which she treats as a craft as much as an art. Throughout her career, Mann has shown little patience for the idea that there’s something mysterious and alchemical behind creativity. “People are a little too in love with this idea of the crazy genius,” she said on the podcast Beyond and Back. “That it’s effortless, that it’s flowing, that you’re born with it. Because songwriting is a skill.”

Yet Mann’s songwriting, particularly on Bachelor No. 2, has its share of magical elements. She has the ability to sublimate a simple folk melody into something weightless and soaring. Her slinky “Calling It Quits,” an initially spare, glum resolution to resign from the rat race, gets an infusion of energy and wonder at the moment she invokes F. Scott Fitzgerald’s novella “The Diamond as Big as the Ritz”; Mann is as wary of the priceless gemstone as Fitzgerald was, but a few regal trumpet blasts (provided by none other than Flanagan) and the crash of cymbals capture its sparkling allure.

Throughout the album, a handful of producers, including Brion and Mann herself, add dimension to her finely wrought melodies and words. Each recording feels like a faithful translation of her rousing performances, with sing-along refrains and strummy intros intact. As a result, despite its scattered genesis over several stints in the studio, Bachelor No. 2 has the organic flow of a late-night set in a small, hushed room. There’s a piano-bar feel to the instrument’s low, steady ramble on “Driving Sideways.” Keyboards clink like a pair of wine glasses on “Satellite,” underlining Mann’s gentle, devastating diagnosis of a confidant’s loss of perspective: “Baby, it’s clear/From here/You’re losing your atmosphere.” Though they’re by no means minimalistic, these arrangements establish a sense of intimacy that’s hard to find on full-band rock records that aren’t deliberately, performatively lo-fi.

The archetypal bar—not the club or the stadium but maybe Largo on a slow night—makes an ideal imagined backdrop for 13 songs bound together by the kind of world-weary wisdom pop culture associates with such settings. Sometimes Mann is the regular slumped over a tumbler of whiskey, wryly enumerating her many disappointments. Other times, she plays the bartender—listening closely, dispensing no-nonsense advice, offering a gruff sort of comfort. Bottled-up energy builds to explosive choruses in “Ghost World,” smashing the veneer of detachment that surrounds Daniel Clowes’ comic-book heroine Enid Coleslaw, a seen-it-all barfly in the body of a teen girl.

As early as “Voices Carry,” Mann had an ear for sudden, surprising hooks. That talent manifests enchantingly on “Red Vines,” a rumination on the meteoric rise of her younger friend Paul Thomas Anderson that starts out placid but lifts off on Mann’s intensifying vocal before the first verse is through, then crescendos straight into a chorus that lingers on dilated vowels. The dark side of “Red Vines” is the way it frames Mann, still under 40 but a decade past her own bright-young-thing years, as both a cheerleader of Anderson’s success and the only one who foresees his inevitable fall from grace. (That she was wrong in using her experience to predict a downfall that never arrived probably says less about their respective outputs than it does about pop music’s youth bias and the misogyny that pervades all corners of the entertainment industry.) She’s constantly anticipating the misfortunes of others. She knows when they’re bound for disappointment, when they’re deluding themselves, when they’ve lost the plot entirely and need to be cut off for the night.

The best song on the album, and the one that most thoroughly embodies its wary, bruised point of view, is “Deathly.” Warmed up by whispered backing vocals from Brion and Juliana Hatfield, it’s a preemptive rejection from someone who’s been hurt too many times to risk heartbreak again. “Don’t pick on me/When one act of kindness could be deathly,” Mann pleads, her emphatic down-strums and simple rhyme scheme inviting a cathartic sing-along. She repeats the brief but evocative title so many times, it finally morphs into a word that’s even more devastating by virtue of its finality: “definitely.” Because she chooses her maximalist moments carefully on Bachelor No. 2, the song’s stratospheric, almost overblown minute-long instrumental outro lends an epic scale to what amounts to Mann’s refusal to keep experiencing emotions.

It was “Deathly” that inspired Anderson to complete the circle of inspiration, making Mann’s music the centerpiece of his 1999 film Magnolia. It makes up the bulk of the soundtrack, alongside a score from Brion (whose history with Anderson dated back to the director’s 1996 debut Hard Eight, on which he collaborated with Mann’s husband, composer Michael Penn). Unfolding over a night punctuated by violent L.A. rain—and culminating in a biblical cloudburst of bullfrogs—Magnolia follows an intersecting cast of lonely, angry, wounded and regretful characters.

In one scene, an abuse survivor and addict named Claudia (Melora Walters) abruptly ends what looked to be a promising first date with a kind, embattled police officer (John C. Reilly) by speaking the opening salvo of “Deathly”: “Now that I’ve met you, would you object to never seeing each other again?” (“I heard that line and wrote backwards,” Anderson recalled in an introduction to the shooting script. “This ‘original’ screenplay could, for all intents and purposes, be called an adaption of Aimee Mann songs.”) The film hinges on this ugly but understandable impulse, to hurt anyone you could potentially care about before they gain the power to hurt you.

Of the nine songs Mann contributed to Magnolia’s soundtrack, including an apt cover of “One” recycled from a Harry Nilsson tribute album, four also appear on Bachelor No. 2: “Driving Sideways,” the muted woman-to-woman warning “You Do” and an instrumental version of “Nothing Is Good Enough,” along with “Deathly.” Magnolia drew more attention to non-album tracks “Wise Up,” which the cast sings in one surreal sequence, and the emotional steamroller “Save Me,” which earned an Academy Award nomination. (Mann got to perform it at the Oscars, but it lost to Phil Collins’ saccharine “You’ll Be in My Heart,” from Tarzan.) Written for Bachelor No. 2 before being appropriated as a Magnolia single, it’s the flip-side of “Deathly.” Mann’s narrator—“a girl in need of a tourniquet”—begs, or maybe dares, an object of affection to pluck her “from the ranks of the freaks/Who suspect they could never love anyone.”

Mann has said that Bachelor No. 2 could’ve come out as early as 1998, but a combination of label gridlock and the marketing cycle around Magnolia, whose soundtrack hit stores just before the film’s December 1999 theatrical debut, delayed its release until the following May. In the meantime, on tour, an impatient Mann sold homemade EPs of her new music, in what she has characterized as a “real DIY fuck-you-record-company-I’m-selling-it-myself” gesture. And after the no-confidence vote from Iovine, she bought back her masters from Interscope, founded the label SuperEgo, and put out Bachelor No. 2 on her own. That courageous move presaged a future where artists with dedicated fan bases wouldn’t need corporate middlemen to access them.

With a boost in name recognition from Magnolia and the Oscars, sales of the album soared past 200,000—easily outperforming I’m With Stupid. (This was an especially decisive victory for Mann: In 1999, then-Sony VP Gail Marowitz had told the Times that “if Aimee sold 70,000 records independently, she would be making more money than if she sold 300,000 on a major label.”) It was in collaborating with Anderson on a movie that eventually played in more than 1,000 theaters that Mann finally found a wider audience primed to appreciate her pithy, disenchanted songs.

Largo’s is the rare story of a small, independently owned music venue that has a happy ending. Flanagan and friends left the original venue for a larger one, Largo at the Coronet, in 2008. Eleven years later, Brion maintains a monthly Friday-night residency, and in December, Mann and Ted Leo are scheduled to play three nights of Christmas shows. “For a while there,” Mann once said, “I was actually going to call the record Underdog Day.” Bachelor No. 2 or, the Last Remains of the Dodo probably makes a grander, more elegant name for a contemporary classic. But the alternate title certainly would have fit.