In the lead-up to the 2016 Presidential election, songwriter Aimee Mann penned a piece from the imagined point of view of then candidate Donald Trump. Titled "Can't You Tell," the song's lyrics echoed a common assumption at the time—that the last thing Trump wanted to do was actually win. "Isn't anybody going to stop me?" Mann sang, as the candidate. "I don’t want this job, my God / Can't you tell / I'm unwell."

It was a funny, acerbic, and insightful take on the character, echoing the qualities of so many of Mann's songs. And even though that particular joke turned out to be far more on us than him, the song helped plant the seed for a fascinating show in the mind of actor/singer Martha Plimpton. "Last year, I had already been thinking, Gee, how can I get somebody to pay me to sing Aimee Mann songs in public?" Plimpton recalls with a laugh.

At the time, Presidents' Day was approaching, so Plimpton decided to use that holiday, as well as the Trump song, as inspirations for her show’s quirky conceit—to perform songs from Aimee Mann's rich catalogue from the point of view of various American Presidents. Ergo its wry title: All the President’s Mann.

"The idea just started to follow its own path," Plimpton says. "Every time I'd play a song, I'd think, Oh, Nixon. Or: That's Jefferson!"

It didn't hurt that Mann's songs have always offered deep dives into the pathologies that drive human behavior—especially the sort evident in characters who have the outsized egos, and unmitigated gall, to do something like run for president. An attention to human psychology has long been a through-line in Mann's work, dating from her roles as lead singer and writer of the '80s band 'Til Tuesday, through her nine solo albums, as well as her 1999, gold-selling soundtrack for Paul Thomas Anderson's film Magnolia.

Mann's songs operate like interventions. They're last-ditch confrontations with characters who have dug themselves so deeply into destructive behavioral patterns, they may never get out. Like most of us, her chosen targets either don't recognize the patterns of their lives or feel too beholden to them to ever consider changing. "Aimee has an inherent curiosity about the ways in which we're compelled by forces out of our control—by our neurosis, or our compulsions—to mess up our lives," Plimpton says.

On her latest album, Mental Illness, which won the 2018 Grammy for Best Folk Album, Mann offers an array of fascinating cases studies, from the pathological fantasist of "Lies of Summer" to the alcoholic in "Philly Sinks" who has the uncanny ability to transfer his addiction to romantic relationships, as well as to modes of thinking. Romantic relationships come in for hard scrutiny in Mann's songs. "She's great at examining how people attach themselves to concepts of love in ways that are twisted or unhealthy," Plimpton observes. "The songs aren't just saying, You hurt me or you're so selfish. They're saying, When you're hurting me, you're hurting yourself."

Plimpton refers to these songs as "psychological indictments." Underlying them, she believes is "a real sense of justice and righteousness." That's especially evident in one piece Plimpton chose to perform in the show, "Amateur." "The song shows the ways in which a person thought they could get away with things just by gas-lighting or by shutting another person down," she says.

"So-called depressing music actually brings you out of depression."

For all the barbs and frustrations expressed in Mann's songs, they have a deep sense of empathy. And as heavy as they can get, Plimpton rejects the notion that they're depressing. "So-called depressing music actually brings you out of depression," she contends. "The songs reflect it back at you so you can finally see yourself. When I listen to her music, it makes me feel like I'm accompanied by some form of truth."

It helps that Mann's music ripples with dark humor, delivered with a deadpan. It's that nuance, as well as Mann's fine sense of character, that makes her songs ripe for a theatrical singer like Plimpton. Though she's far better known as an actor, Plimpton has been singing her whole life. She appeared in her first musical at age 9, the Elizabeth Swados piece The Haggadah at The Public Theater. She first took part in the American Songbook series with her 2010 show Martha Plimpton Sings? In it, she used cover songs to tell the story of her years growing up on the Upper West Side of the '70s and '80s. "It was in a city that no longer exists, in a neighborhood that now barely exists," she says. "It was all the stories of danger and interest and joy."

In the music that she chose for that piece, as well as the new one, Plimpton looks for the story in the song. This time, by sticking with just one songwriter, whose work she repurposed in a political context, her show offers something both timely and unique. "What I hope is that the show will help people remain engaged, instead of checking out," she says. "I also hope that they find it funny and, to some degree, that it breaks their heart."

Jim Farber, the former chief music critic of the New York Daily News, currently contributes to the New York Times, the Guardian, Entertainment Weekly, and many other outlets. He is a three-time winner of the ASCAP–Deems Taylor/Virgil Thompson Award for music writing.