You remember the scene in Paul Thomas Anderson’s sprawling 1999 film, Magnolia. It’s about to start raining frogs, but right before is a moment of hopeless reckoning for every character—illness, addiction, sexual abuse, abandonment. It’s time for an intervention. It’s time for an Aimee Mann song.

Tom Cruise, Julianne Moore, Philip Seymour Hoffman, William H. Macy, John C. Reilly, and a moribund Jason Robards all break into “Wise Up.” This is not a Hollywood musical, where professional voices send us to fantasy. They sound like us—they are us—singing along to Aimee Mann. The movie stars are complicit with us in this pact. We admit that we lack wisdom, and even if we get it, it won’t be enough. Aimee Mann probably doesn’t know any more than we do, but the song does.

Getting what you want, she tells us, can turn into a nightmare:

It’s not what you thought
When you first began it
You got what you want
Now you can hardly stand it, though
By now you know
It’s not going to stop
It’s not going to stop
It’s not going to stop
’Til you wise up

The song gets darker from there. There’s no cure. One endures until one can’t. The final words? “So just give up.” There is nothing more to say. (Mann was nominated for an Oscar for a different song from Magnolia, “Save Me,” which lost to Phil Collins’s “You’ll Be in My Heart,” from Tarzan.)

Telling It Like It Is

Sometimes I want music to comfort me, but sometimes I want what Ralph Waldo Emerson called “the rude truth.” And here was a voice giving it to me plain. This voice doesn’t want me to like her. This voice has no guile, no P.R., no unctuousness. It is a voice that says I’d better wise up, and then I’d better wise up again for expecting things to get better.

One song, “Soon Enough,” has a video of Mann receiving an intervention, but really every Aimee Mann song is an intervention. Not that it’s any of our business, but she appears to be happily married to fellow singer-songwriter Michael Penn, brother of Sean, for nearly 30 years. Where does all this Weltschmerz come from?

I asked Elvis Costello, who wrote a couple of exquisite songs with her, about the source of her dark muse. He paused and said, “Do you know Aimee?”

When I reported this to Mann, who spoke to me via Zoom from her Los Feliz living room, she laughed. To know her is to know the answer to this question. Her fans recognized her as one of the nihilists in The Big Lebowski, and while the casting was tongue in cheek, she was a natural.

Aimee Mann is not a nihilist, but she does not sound like much of a believer, either. “I think people are always writing about the ghosts of their relationships with their parents,” she tells me. “That’s what you grow up with and you see it echoed in your own relationships.”

In Mann’s case, her mother and her mother’s boyfriend kidnapped her at the age of three, and her father had to hire a detective to track her down in Europe. “There are always echoes of abandonment,” she says. “Once I was back, I never saw [my mother] again until I was an adult, so there are echoes of chaos and upheaval.” Nothing really explains Aimee Mann, but this level of loss surely contributed to her sublime devastation.

Where does all this Weltschmerz come from?

Indeed, to peruse her lyrics is to recount a series of devastating blows: “Nothing is good enough / For people like you / Who have to have someone take the fall / And something to sabotage / Determined to lose it all”; “My heart is a poor judge / And it harbors an old grudge”; “You’ve got a lot of money, but you can’t afford the freeway.”

Many singer-songwriters use unrequited love as a muse, and if they become happily partnered, they move on to the third person or to summoning the bad old days. Mann seems to have many friends with addictions—drugs, sex, their illusions and delusions—and confrontation is her serial muse.

I do not feel in the least bit confronted when Mann and I discuss her new album, Queens of the Summer Hotel, songs for a stage adaptation of Susanna Kaysen’s Girl, Interrupted, which inspired a definitively late-90s film adaptation where the iron walls of a psych ward could not cage Winona and Angelina.

Mann’s songs follow McLean Hospital’s literary trail of Robert Lowell and Sylvia Plath, charting borderline-personality disorder, incest, electroshock, suicide, and transfiguration at the Frick Museum, when Kaysen, seeing Vermeer’s Girl Interrupted at Her Music, has an epiphany.

“She’s talking to her therapist,” Mann tells me, “and remembers having a relationship with her English teacher, who takes her to the Frick museum, [where] she [sees] this Vermeer painting that affects her deeply.” This is from the final chapter in the book, a beautiful and powerful piece on its own, and there is nothing about it in the film. Vermeer looked into the souls of everyone who posed for him, perhaps judging them as devastatingly as Aimee Mann does:

It showed a girl
A startled glance
And something in
The circumstance
Almost felt like a warning—
now it’s gone

A track and video dropped in advance for “Suicide Is Murder,” which starts with Kaysen’s observations but turns into an Aimee Mann song. Mann and I have both lost loved ones to suicide, and we know that there are wounds that never heal. You would think this would be a universal feeling, but no one has written a song about it like Aimee Mann has.

’Cause suicide is murder
You’ve got to have
Motive, means, and opportunity
Suicide is murder
Pre-meditated, rehearsed tragedy

These lyrics are perhaps her most devastating yet. They’re a public service, but also beauty and truth, a truth that most of us can’t handle.

Are her new songs too bracingly honest? Maybe for some. But I keep coming back to Aimee Mann, casting a cold eye. And she tells me that maybe I can cheer up a little. Maybe it’s not too late to wise up. This intervention she’s having with us could still have a silver lining. “There is something comforting about telling it like it is.”

Aimee Mann’s Queens of the Summer Hotel is out now

David Yaffe is a professor of humanities at Syracuse University. He is the author, most recently, of Reckless Daughter: A Portrait of Joni Mitchell