4 Songs That Prove Aimee Mann Is a Master of the Weeper

Some songwriters just have a knack for delivering sorrowful songs. Aimee Mann stands out as one of the finest in that department. On top of her writing skills, Mann’s voice expertly evokes downcast feelings.

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We could have made this list of Mann’s essential weepers much longer. But we decided to keep it at four so you can try to compose yourself.

“Wise Up”

Mann’s music soared to its greatest level of exposure thanks to the 1999 film Magnolia. Director Paul Thomas Anderson essentially wrote the movie based on inspiration gleaned from several Mann songs. One of those was “Wise Up”. Interestingly, Mann wrote that song for Jerry Maguire in 1996, but it didn’t appear in the film. (It did make the soundtrack.) Anderson felt so strongly about it that he created an entire scene of various characters in the film stopping what they were doing to sing along to it. And you can kind of understand why they would. Featuring some of Mann’s most concise lyrics and a stunning melody, “Wise Up” manages a direct hit to the heart.

“It’s Not”

Mann rode the wave of the exposure from Magnolia by releasing her album Bachelor N. 2, Or The Last Remains Of The Dodo in 2000. She released that record on her own after she was dropped from her label when they didn’t feel she was commercial enough. After the massive critical acclaim of Bachelor No. 2, Mann had the world’s ear for her follow-up. If anything, Lost In Space, released in 2002, wallows in an even deeper funk than the previous album. It culminates in the aching closing track “It’s Not”. The narrator’s hopes are constantly dashed by the refrain, which brings her back to cold reality every time she imagines a better outcome.

“That’s How I Knew This Story Would Break My Heart”

Mann tried something a little bit different on the 2005 album The Forgotten Arm. It’s a concept album, complete with a storyline that loosely connects all the songs. She does an excellent job throughout of making each song relatable to listeners who might not know the context of where she is in the story. “That’s How I Knew This Story Would Break My Heart” is a particularly sad, pretty highlight of the LP.  The song takes place at a point when the two main characters are realizing that they’re past the point of no return for saving their relationship. That bit of perspective doesn’t spare the narrator any heartbreak as she prepares to go on her way.

“Philly Sinks”

In the press leading up to her 2017 album Mental Illness, Mann made no secret of the fact that she leaned into her reputation as a singer of sad songs for the record. She also explained how she found the waltz tempo to be particularly conducive to the weepers, so she included a few of those. Among those, “Philly Sinks” comes to the forefront. The song tells the story of a guy who, in spite of the struggles in his life, manages to captivate his share of romantic partners. And when he inevitably crashes to a new low, he takes those partners with him. It’s a devastating character sketch and cautionary tale all at once.

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