Aimee Mann and Elliott Smith occupied the same small gravitational field in late-1990s Los Angeles, and the records they made in that proximity carry the same temperature. Both were working against the grain of what the major-label system wanted from them. Both found their way to Jon Brion, a producer and multi-instrumentalist whose instinct was always to serve the song rather than the market. And both spent formative nights at Largo, a club on Fairfax Avenue in Hollywood where Brion hosted a weekly Friday-night residency, beginning in 1996, that became one of the most consequential rooms in the singer-songwriter tradition since the folk revival. The connection between Mann and Smith is a shared artistic position, arrived at independently, that shaped two of the most serious bodies of work the 1990s produced.

Mann had been through the industry's machinery before Smith arrived in Los Angeles. Her band 'Til Tuesday had a top-ten single with "Voices Carry" in 1985, peaking at number eight on the Billboard Hot 100, and when the band dissolved around 1990 she moved into a solo career that the labels consistently misread. Her first two solo albums, Whatever in 1993 and I'm with Stupid in 1995, received strong reviews and found no commercial traction. The industry response, as she described it later, was a recurring instruction: the songs needed to be faster, more up-tempo, more like singles. She had been told so many times that nobody wanted slow and sad that she had started to believe it. The realization she eventually arrived at was simple: as a listener, she wanted exactly that. She cited "that sort of classic folk music or Elliott Smith" as the music she actually loved. That sentence is a small map of her aesthetic. It places her in a lineage running from Nick Drake and Joni Mitchell forward, and it places Smith in that same lineage beside her, as a peer rather than a successor.

Smith had signed to DreamWorks Records in 1997, a move that brought its own pressures after years on independent labels Cavity Search and Kill Rock Stars. His vocal approach, described by those who wrote about him as a "whispery, spiderweb-thin delivery," was built on multi-tracked harmonies fingerpicked and recorded to tape, a method that owed as much to the Beatles as to the American folk tradition, and that resisted the kind of radio-ready clarity the major-label system preferred. XO, his 1998 DreamWorks debut, was produced by Smith alongside Tom Rothrock and Rob Schnapf, and it announced a musician willing to reach for orchestration and arrangement without surrendering the intimacy that had made his earlier records so affecting. He was a regular at Largo during the period when Mann was also finding the room essential. Brion's Friday-night gig drew Mann, Smith, Fiona Apple, and Rufus Wainwright into the same orbit, and the club became, as one account put it, a space to work out new material and avoid the glossy demands of the industry. It was a room where the song was the whole point.

Brion is the figure who holds much of this story together. His production credits on Bachelor No. 2, the album Mann recorded in 1999 and released on May 2, 2000 on her own SuperEgo label, reflect the same seriousness of purpose he brought to his work across the Largo years. On Bachelor No. 2, Brion produced several tracks and played drums throughout the record. Benmont Tench, the founding keyboardist of Tom Petty and the Heartbreakers, contributed piano and Chamberlin. Patrick Warren added piano, accordion, and keyboards across multiple tracks. Mann co-produced the album alongside Brion, Buddy Judge, Mike Denneen, and Brendan O'Brien, taking more control over the production than on any previous record. The album contains four songs that had already appeared on the Magnolia soundtrack, including "Save Me," which earned Mann an Academy Award nomination. Paul Thomas Anderson had begun writing the film after hearing Mann's "Deathly," a song from the same sessions, and building his script outward from there. Bachelor No. 2 also includes "The Fall of the World's Own Optimist," co-written with Elvis Costello, a pairing that signals exactly how seriously Mann took the craft of the lyric.

What Mann and Smith shared was a commitment to the sentence. Both wrote lyrics that rewarded reading as carefully as listening, and both built their music around the architecture of voice and guitar or piano, with arrangement serving the word rather than decorating it. Mann's sardonic precision and Smith's tender devastation are different tools for the same project: the examination of interior life with enough specificity that the listener feels recognized rather than merely moved. The tradition they were working in runs from Leonard Cohen's debut in 1967 through Joni Mitchell's Blue in 1971 to Nick Drake's Pink Moon in 1972, and what connects those records to Mann and Smith is seriousness of purpose. The lyric carries the weight. Everything else is in service of that.

The Largo scene dissolved, as scenes do. Smith died in October 2003. Mann continued, releasing The Forgotten Arm in 2005, @#%&*! Smilers in 2008, and eventually Queens of the Summer Hotel in 2021, an album built around the music of a stage adaptation of Susanna Kaysen's Girl, Interrupted, the memoir about Kaysen's time as a patient at McLean Hospital in the late 1960s. When she appeared on Sound Opinions in 2021 to discuss the five albums that had shaped her, she placed Smith's XO, specifically the track "Sweet Adeline," in that list alongside Neil Young. The citation is precise and it is generous. It acknowledges a debt that runs in more than one direction, because the Largo years shaped both of them, and the records they made in that period belong in the same conversation, not because they sound alike but because they were made with the same conviction: that a song, built carefully and sung honestly, is enough.