How Aimee Mann’s unrelentingly honest music was the perfect album for Carrie Courogen

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“Every song on [Bachelor No. 2 or, the Last Remains of the Dodo by Aimee Mann] is perfect. It's a perfect album from start to finish. It's just so insightful and so human and so unrelentingly honest. It's often heartbreaking, but then it's describing heartbreak in a way that is funny, or in a way that has a sense of humor.” Photo credit: Sylvie Rosokoff

New York-based writer Carrie Courogen has been telling important stories for more than a decade. She’s worked with heavy hitting outlets such as Vanity Fair, Tatler, and Condé Nast. Her acclaimed biography of Elaine May, Miss May Does Not Exist: The Life and Work of Elaine May, Hollywood’s Hidden Genius came out in June of this year, introducing previously unaware folks to the brilliant and challenging show biz legend. 

More: Miss May Does Not Exist casts Elaine May as the leading lady of her own life (The Treatment, 2024) 

For her Treat, Courogen fangirls over Aimee Mann's 2000 album, Bachelor No. 2 or, the Last Remains of the Dodo. She says that she’s constantly inspired by the way that Mann explores human inadequacies and the imperfect way most of us are making our way through life. Courogen draws parallels between Mann's struggles with the music industry and Elaine May's battles with the studio system, noting both artists' resilience in the face of corporate pushback and their ability to transform challenges into commentary. 

This segment has been edited and condensed for clarity. 

I love the music of Aimee Mann. I am constantly inspired by the way that she explores human inadequacies and the way we are all fumbling and failing our way through life. 

When I was writing my book, [Miss May Does Not Exist: The Life & Work of Elaine May, Hollywood’s Hidden Genius], I kept coming back to Aimee Mann’s album Bachelor No. 2 or, the Last Remains of the Dodo, which was released in 2000, and part of it is comprised of songs that she wrote for Paul Thomas Anderson's Magnolia, or rather, she was writing while he was making a movie, and he structured a lot of the script around it. But really, the big story about Bachelor No. 2 is Aimee Mann's ongoing issues with the label that she was working with. And they kept coming back to her, saying, ‘You know, we don't hear a single’ or ‘This is too literary, people won't understand this’, ‘This can't play on radio. You can't do this. You can't do that. And she kept saying, Well, why not? 

Aimee Mann left her label and released Bachelor No. 2 independently at a time that was like the dawn of streaming, and very few artists made that leap. And I kept thinking about how her struggles with the label and her response to it reminded me so much of Elaine May's struggles with the studio system and the ways in which she pushed back against it, this real desire to do something that is unique and true to oneself, and getting pushback from the corporate powers that be, saying you can't do that, this common, shared theme that I think they both have of constantly asking, Well, why not? And then when they're told why they can't, or they're told to behave in a certain way, then sort of turning the material into commentary on the struggle itself.

Every song on that album is perfect. It's a perfect album from start to finish. It's just so insightful and so human and so unrelentingly honest. It's often heartbreaking, but then it's describing heartbreak in a way that is funny, or in a way that has a sense of humor. Because, if you don't have that sort of sense of humor, you just kind of collapse. 

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Rebecca Mooney