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Aimee Mann is tugging at her dummy’s broken mouthpiece. Sitting on a red couch in her L.A. home, she explains how the monocled Charlie McCarthy doll, fashioned after ventriloquist Edgar Bergen’s puppet, became more famous than its owner in the 1930s. “I had two at one point,” Mann admits with a laugh, wearing a plain blue T-shirt and her trademark, thick-rimmed eyeglasses. She’s completely mindful of how creepy Charlie looks with his mouth slack-jawed open as she moves it out of the frame of our Zoom call. “I’m the person who sees it at a flea market and I have to buy it.”
An eccentric artifact with its own complicated relationship to celebrity, Charlie McCarthy sounds ripped from the lyrics to one of Mann’s songs. Her refined guitar pop is filled with attuned details and characters more often associated with the best short stories, as Mann applies her sharp wit to cut to the core of issues like depression, love, and disappointment. She’s so good at bringing underdogs to life in her work, in part, because she’s had so much practice punching up throughout her career: Mann has fought hard to chart her own course in the music industry over nearly 40 years, having endured several label misfires that informed her defiantly independent approach.
Raised in Richmond, Virginia, Mann was exposed to storytelling music early on as she listened to country crooner Glen Campbell’s ambling 1969 hit “Galveston” around the house. She went on to study voice and bass at Berklee College of Music in Boston and fronted an art-punk trio called the Young Snakes. They were a prelude to ’Til Tuesday, the sleek synthpop group she formed in 1983, whose aching ballad “Voices Carry” became an MTV staple and Top 10 hit two years later. The millions-selling single was one of the first songs Mann ever wrote on her own.
’Til Tuesday released three albums on Epic Records, home to decade-defining stars including Michael Jackson and Cyndi Lauper, but broke up in 1989 under pressure from the label to make another smash. From there, Mann began to work on her own solo material, crafting intricate songs that slyly indict the record industry; even today, it can be difficult to parse which of her lyrics are jabs at exes or label suits.
With 1999’s Bachelor No. 2 or, the Last Remains of the Dodo, which is celebrating its 20th anniversary with a deluxe reissue this week, Mann took full command of her output and co-founded SuperEgo Records, an avenue that has allowed her to explore ideas including a boxing-inspired concept album, a wry Christmas collection, and her latest, 2017’s Mental Illness, a canny collection of spare acoustic songs that netted her a Grammy for Best Folk Album.
Mann, who turned 60 this year (a friend gave her a gluten-free cupcake from a safe, six-foot distance), is dryly funny and perceptive while discussing the music that shaped her life. She also continues to side-eye the music industry at large in no uncertain terms: “Obviously every system is garbage, because people are terrible,” she sighs at one point, before breaking into conspiratorial laughter. Yet her unabashed love of music—especially classic folk harmonies, acoustic guitar, and the work of her husband, singer-songwriter Michael Penn—still nourishes her soul. “When I hear a thing that gets me emotionally, I will listen to it over and over and over,” she says. “If you add up all these songs and cram them together, it’s like, ‘Oh, yeah, that’s what I sound like.’”
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