Aimee Mann writes about the devils you don’t know and the devils you think you do. Especially on Bachelor No. 2 (Or, The Last Remains Of The Dodo), her third album, she chronicles the inner monologues and outer arguments of people fighting hard to remain lonely and miserable, because it’s familiar and perhaps even comfortable and because it’s certainly better than the regret and misery they know will accompany the inevitable end of whatever romantic entanglement they’re resisting. Everything ends in regret and misery, so why bother? “Just one question before I pack,” Mann sings, “when you fuck it up later, do I get my money back?” And that’s the album’s very first song.

Such either/or predicaments were enough to inspire Paul Thomas Anderson to write a very long and ambitious ensemble drama based on demos of Mann’s songs, some of which ended up on the Magnolia soundtrack in 1999 while others debuted on Bachelor No. 2 the next year. And if his screenplay takes three hours to approximate the complex conundrums she sketches out in just three minutes… well, who could possibly match Mann in terms of barbed wit, incisive insight, and just enough ambiguity to make you wonder which devil is worse – the known or the unknown. Is heartache better than solitude? Or is that old adage about loving and losing being better than not loving at all just a bunch of bullshit? Anderson ended Magnolia on an optimistic note, with Melora Walters’ addled cokehead flashing a lovely grin at John C. Reilly’s earnest cop, which may mean that Anderson understands nothing about Mann’s music. To quote the title of her 2008 album, @#%&*! Smilers.

Histrionic where Mann’s songs are stoic almost to the point of humor, Magnolia should have been the career boost she needed. It’s hard to believe now, when Mann is widely revered as one of the finest songwriters of the 2000s, but she was a tough sell in the late 1990s. She’d had another life in the 1980s as big-haired singer-bassist for the Boston-based one-hit wonders ’Til Tuesday, but what a one hit to have: “Voices Carry” finds sharper shades of emotion than most New Wave hits could muster, and had a massive hook to boot. Her solo debut, Whatever, released in 1993 on forgotten label Imago Records, was well reviewed and got some MTV airplay, but that label’s forgotten for a reason: It folded not long after Whatever was released. Her follow-up didn’t fare much better: Geffen looked like a step up, but that label sat on I’m With Stupid for two years, finally releasing it in late 1995 with no fanfare.

But Mann was a regular at a small Los Angeles called Largo, which by the late ’90s was becoming popular as a gathering spot for idiosyncratic singer-songwriters, with lines forming around the block. On any given night you might see a set by a musician like Fiona Apple or Rufus Wainwright or Mann’s husband Michael Penn (best known for his 1989 hit “No Myth” and for his own conflicts with labels). Coverage of the club and the community around it often focused on Mann. As she told The New Yorker in 2008, “Almost all of my friendships are a direct result of going to Largo, meeting these people, and trying to mix comedy and music… Largo’s the hub of my social life, really.”

One of those friends was Anderson, and he made no bones about the inspiration: At one point a character directly quotes Mann’s song “Deathly” (“Now that I’ve met you, would you object to never seeing each other again?” in a scene that proves that even the best lyrics sound flat when spoken aloud), and right before the third act he stops the film cold to have all his characters sing along with “Wise Up.” The latter scene was the film’s biggest risk and its biggest payoff, using a music video technique to crack the fourth wall and show the degree to which we find ourselves reflected in our favorite songs. “Save Me,” a new tune penned specifically for the final scenes, even got an Oscar nomination, although Mann lost to that Phil Collins song from Tarzan.

Any label worth the gold records on its walls should have been able to run with that kind of momentum, but Geffen had been absorbed by Interscope, and Interscope didn’t hear a hit. Did they really think Mann was going to be the next Natalie Imbruglia or the next Sheryl Crow? Finally released in 2000 and featuring three-and-a-half songs from the Magnolia soundtrack (“Nothing Is Good Enough” had been an instrumental but she added vocals for the album), Bachelor No. 2 may be Mann’s best album precisely because it reveals an artist still fighting to define herself as herself. Aside from a few drum loops more like the ‘90s artists her label no doubt wanted her to emulate, very little here sounds dated or archaic, as she channels the Brill Building and other ‘60s pop sounds into carefully composed songs about untidy emotions. Locating an incredibly fine balance between romantic and bitter, Mann brooks no hope for a happy ending but never truly resorts to cynicism either.

A few reviewers at the time commented on the limitations of her voice, which doesn’t have much range or power but makes up for it with expressiveness, wit, and personality. “So don’t work your stuff, because I’ve got troubles enough,” she sings on “Deathly,” and a lesser singer might have elided that word “stuff,” which sounds like it’s there for the easy rhyme. But Mann leans into it, burdening it with so much sexual desire that the stakes become starkly clear. Throughout Bachelor No. 2 she acknowledges the existence of sex without letting it take up the entire screen. Closer “You Do” is about a woman trying to find a guy’s heart through his cock, and Mann describes the enterprise as foolish. It’s an anti-love song, a ballad of self-delusion, placed at the end of the album to ensure there’s no closure, yet the gentleness of the melody and the tenderness of Mann’s performance allow her to stop shy of condescension. Instead, she sounds sympathetic.

A common assumption is that singer-songwriters, especially women, are working in an exclusively autobiographical vein, baring their souls and fictionalizing nothing. Mann’s songs are full of characters, some based on friends, some based, yes, on herself, many others invented whole cloth. “Red Vines,” the album’s first single and one of Mann’s finest songs, is ostensibly about her friendship with Anderson, who often seemed fueled by licorice and cigarettes during recording sessions but who was moving from indie auteur to Hollywood firebrand. The song is sweet and protective, open-hearted, hoping the travails she faced as an artist don’t befall him.

“Ghost World,” on the other hand, sounds much more fictionalized, as Mann follows a recent college graduate biking around his hometown and does pretty much nothing. “So I’m bailing this town,” goes the chorus, “or tearing it down, or probably more like hanging around, hanging around.” Every “or” in those lyrics stings, as the kid narrows his horizons until all he can see of life is what’s right in front of him. Mann understands he’ll be left behind, but the small town he knows like the back of his hand is less intimidating than the big world beyond it. He’ll go with the devil he knows.

Mann faced a similar choice when Geffen rejected Bachelor No. 2. She could stick it out with the label or go off on her own. Geffen sold her masters back to her and in February 2000, she released the album via SuperEgo Records, the label she cofounded with ’Til Tuesday drummer Michael Hausman. At first it was only available by mail order through her website, but it quickly sold 25,000 copies. That was an astronomical amount for an artist with no label support, but it was more than enough to secure a distribution deal and get Bachelor No. 2 in record stores by May.

And perhaps that’s where the dodo comes in. Mann couldn’t have known it at the time, but that subtitle proved weirdly prescient. The dodo, of course, is a cautionary tale of evolution: Native to the African island of Mauritius, it was a plump, flightless bird reportedly too stupid to fear humans and therefore easy prey for passing sailors. They were hunted to extinction and now exist only as taxidermied museum displays. Perhaps Mann intended the metaphor to apply to her ambivalent lovers, but it’s become an apt stand-in for then record labels that were slow to adapt to emerging digital technology. More and more artists were taking their careers into their own hands, parachuting away from falling majors, releasing their music on their own terms, and pocketing more of the profits. Wilco gets more credit for leading this charge, but Aimee Mann was already exploring the commercial possibilities of the internet more than a year before Yankee Hotel Foxtrot streamed for free.

Bachelor No. 2 is Mann thumbing her nose at the music industry. Many of these songs are explicitly about the suits who told her they didn’t hear a single, or that she wasn’t sexy enough, or that she needed to jazz up her songs somehow. And she pulls no punches: “Critics at their worst could never criticize the way that you do,” she spits on “Nothing Is Good Enough.” “No, there’s no one else I find to undermine or dash a hope quite like you, and you do it so casually, too.” You can almost imagine her writing the entire song during a particularly tedious and condescending meeting.

Songs about music industry woes are common and rarely compelling, mainly because they presume a connection with an artist or an investment in their brand and storyline. But what makes “Nothing Is Good Enough” and “Calling It Quits” different from all the no-sellout anthems of the ’90s is that Mann treats these labels — but not the men who represent them — as she would treat lovers. These contracts are dalliances, affairs that soured long before they ended, built on promises they had no intention to keep. That makes her songs relatable; when she sings, “He’s a serious mister, shake his hand and he’ll twist your arm,” she might be talking about an ex-boyfriend or a creepy client or a bad boss. You recognize the toxicity even if you’ve never glad-handed an A&R guy. More than that, the choice is similar to the ones that face every character in Mann’s songs: Go it alone or risk the heartache. Mann chose to strike out on her own, not only writing an enduring album about the experience but selling a boatload of copies by herself, without resorting to a deal with the devil.