Before there was Fiona, before Elliott, before Kanye, there was Aimee. It wasn’t just a producer-artist relationship; it was a musical meeting of the minds that rescued Aimee from the “new wave” constraints of the ’80s and helped her find her voice as one of the greatest living songwriters.
“Working with Jon was really just very musically exciting and interesting — just watching how creative he was in the studio. And I felt like I was writing better songs and learning a lot from him, learning more about making records, because we did have some time to experiment a little bit.”
Aimee Mann
Key albums
- Whatever (1993) – The debut that started it all
- I’m with Stupid (1995) – Peak Mann-Brion collaboration
- Bachelor No. 2 (2000) – A classic that inspired Magnolia‘s soundtrack and script
- Magnolia soundtrack (1999) – Mann songs + Brion score = perfection
Essential tracks
- “Stupid Thing” – Relationship regret as power pop
- “That’s Just What You Are” – Tenderness without sentimentality
- “You’re with Stupid Now” – Friendship and bad decisions
- “Save Me” – Oscar-nominated heartbreaker
- “Wise Up” – Magnolia‘s emotional core
- “I Believe She’s Lying” – Their co-write on Brion’s solo album
Live chemistry: How Aimee Mann and Jon Brion found each other
Jon Brion joined ‘Til Tuesday as a touring member in 1987, right around the time the new wave band was winding down. The chemistry between Jon and Aimee was evident long before the solo records. You can see the sparks flying as far back as their time in ‘Til Tuesday. Check out this classic footage of them at Late Night with David Letterman, where Jon’s guitar work perfectly complements Aimee’s unmistakable vocals:
When Aimee was ready to go solo, Jon was right there. However, it wasn’t a smooth ride with the “suits.” In a revealing interview with Stereogum, Aimee recalls label executives questioning Jon’s credentials, asking, “I want her, but who’s this Jon Brion guy? I want her to work with a real producer.”
Thankfully, Aimee stuck to her guns. While Jon didn’t produce the entire record (Tony Berg was brought in for parts), his influence is the album’s heartbeat. He didn’t just play instruments; he brought “interesting sounds” (including those vintage keyboards like the Chamberlin) that moved Aimee away from the slick ’80s production and into a more organic, timeless space.
Aimee Mann and Jon Brion: The three albums that matter
Whatever (1993)
Mann’s solo debut remains a masterclass in emotional sophistication wrapped in pop hooks. Songs like “I Should’ve Known” and “Stupid Thing” deal with relationship wreckage, but never wallow — Mann’s too smart for that, and Brion’s production gives her anger and sadness equal weight.
The Guardian ranked “Stupid Thing” among Mann’s greatest songs, noting how it captures the particular frustration of “realizing too late the mistake of getting involved with a person who probably won’t change.” Brion’s arrangement, built on Mann’s bass, his Mellotron, and a deceptively simple guitar line, makes heartbreak sound almost jaunty. Almost.
I’m with Stupid (1995)
If Whatever introduced the Mann-Brion sound, I’m with Stupid perfected it. This is where their collaborative chemistry really ignites. Mann plays bass, guitar, vocals, and even drums on one track. Brion plays… basically everything else, from distorted nylon guitar to tack piano to bass harmonica.
“You’re with Stupid Now” might be the peak — a song Mann wrote about a friend (British politician Tony Banks, whom she met during her London period), but which could apply to anyone who’s watched someone make terrible romantic decisions. As Mann told Stereogum with characteristic humor: “When I was writing [‘You’re with Stupid Now’], I was like, wow, this is the story of our friendship, which is that he’s a fucking idiot… But he’s a much better guitar player.”
As for working together with Jon Brion on his song, Mann shares:
The song “You’re With Stupid Now” is very different. It’s got a real acoustic sound. It almost has this very fluid, almost jazz guitar [that] I think Jon is playing, which really ties everything together. His sense of melody is so fantastic. His solos are fantastic. He plays four separate solos [on “All Over Now”] that are all so great. I remember teaching myself how to play them because I was trying to become a better guitar player.
The album’s not all caustic wit, though. “That’s Just What You Are” is devastatingly tender, while “I’ve Had It” channels Mann’s label frustrations into pure new wave energy. As she explained, they never played it live — too specific to that moment — but it’s a time capsule of industry bullshit circa 1995.
Bachelor No. 2, or the Last Remains of the Dodo (2000)
Originally rejected by Interscope as “not commercially viable,” the album went on to become one of the most influential releases of the decade. Mann famously bought back the rights and sold it online herself — a move that now feels prophetic.
This is the album that Paul Thomas Anderson used for Magnolia. Songs like “Save Me,” “Wise Up,” and “Deathly” are so perfectly crafted that Anderson structured parts of his film around them. The incredible roster of musicians backing Mann — Michael Penn (her husband), Juliana Hatfield, Grant Lee Phillips, Buddy Judge, Jen Trynin, and of course Brion — created something that felt both intimate and cinematic.
To support the record, Mann and Penn created Acoustic Vaudeville, a touring concept that mixed music and stand-up comedy at LA’s Largo (where Brion held his legendary Friday residency). Comedians like Patton Oswalt, David Cross, and Janeane Garofalo joined them, creating a uniquely LA alternative scene moment.
“Most of the best songs I have ever recorded were written while the album was being made. That happened on both Aimee Mann albums I did. She’d say, “I’ve got a new song — can I record it?” We’d put it down, vocal and guitar, I’d put most of the overdubs on it, and later drums. Most of the overdubs were put on probably forty minutes after she was done putting on the vocals.”
Jon Brion’s interview to American Songwriter
The Magnolia connection
The relationship between Mann, Brion, and Paul Thomas Anderson is one of those perfect creative triangles. Brion met Anderson through Mann’s husband Michael Penn in 1996, and Anderson fell hard for Mann’s music. He didn’t just license a few songs for Magnolia — he shaped the film around them.
“Save Me” earned Mann an Oscar nomination. “Wise Up” became the film’s emotional centerpiece, with the entire cast singing it in one of cinema’s most memorable musical moments. Anderson understood what Mann and Brion had been doing all along: making sophisticated pop that could hold real emotional weight.
Decades later, Aimee Mann still performs “Save Me,” carrying the torch for the songs they built together with Jon Brion. Below is the live recording made in 2024.
The sound Aimee Mann and Jon Brion built together
The Mann-Brion partnership essentially created a genre that didn’t have a name yet. When Whatever came out in 1993, there wasn’t really a category for sophisticated, melodically complex indie pop with vintage instrumentation and literary lyrics.
By 2000, there was. And it was everywhere — at least in the clubs around LA’s Largo, where Brion held court and a generation of singer-songwriters learned what was possible when you stopped worrying about radio formats and started worrying about emotional truth.
The sound — which Stereogum aptly named “LA alternative” — was based on:
- Vintage instruments as emotional texture – Chamberlins, Mellotrons, pump organs, harmoniums. Brion didn’t use them for nostalgia; he used them because they could express things a standard keyboard couldn’t.
- Arrangements that serve the lyric – Nothing gratuitous. If a song needed strings, it got strings. If it needed to be stripped bare, everything came out.
- Bass-forward production – Both Mann and Brion played bass on these records, often trading parts, creating rhythmic foundations that were melodic without being showy.
- Vulnerability in hi-fi – These weren’t lo-fi indie records, but they never sacrificed intimacy for polish.
How Aimee Mann and Jon Brion worked together
What makes the Mann-Brion collaboration special isn’t just their individual talents — it’s their complementary working style. As Brion explained about co-writing “I Believe She’s Lying” (which appears on his solo album Meaningless): “The way we wrote together was often, one of us would start something and get stuck and play it for the other and go, ‘Hey, what do you think of this?’ And, usually, the other person would have a workable answer.”
Mann describes herself as better at finishing things, while Brion excels at sparking ideas. It’s a classic producer-artist dynamic, except they both wear both hats at different times.
As Mann told Rolling Stone in 2021:
“I think he’s a phenomenal musician and has an incredible sense of melody.”
She also added, with gentle teasing:
“Jon has at least 10 albums’ worth of material. I think he has a hard time saying anything is finished, whether he’s producing or doing his own songs. Jon’s a perfectionist.”
The legacy
As Grant Lee Phillips, who worked with both artists, told Rolling Stone:
“I’m such a fan; he’s just a really special guy to begin with. As a musician, there’s really no one like him. I mean, there’s a lot of people who play a lot of things, but Jon’s plugged into some other part of the universe.”
That “other part of the universe” is what Mann heard back in the late ’80s when Brion was just a guy playing guitar in her touring band. She knew then what the rest of us would figure out over the next two decades: Jon Brion isn’t just a producer. He’s a complete musical mind who needs the right collaborator to fully realize his vision.
With Aimee Mann, he found that collaborator. And together, they changed what indie pop could be.