The indie singer/songwriter completed two projects this year--a musical with a Tony-winning playwright and an EP on her own.

When Erin McKeown realized that her career had found its level, she was able to move forward into one of her most creative periods. She’s had stretches that got the kind of attention that could take her to another level—whatever that means—but indie singer/songwriters only get so big. Big enough to tour, but not with their bands. Big enough to tour, but not to get mailbox money. It took time to make peace with that cold truth, even though she long suspected it.

“I didn’t spend a tremendous amount of time to look or sound a certain way to have success, but there was some of that for sure,” says McKeown, who plays an early show Saturday night at Gasa Gasa. “After the despair of realizing you’re at the lonely moment, there’s a tremendous amount of liberation that comes from that to make whatever music I want to make with whoever I want to make it with.” 

That freedom translated to the EP According to Us, and Miss You Like Hell, a musical she has worked on for the last four years with Tony and Pulitzer award-winning playwright Quiara Alegría Hudes. “I absolutely won the collaborator lottery because Quiara is a tremendous artist and collaborator,” McKeown says. “She has become one of the most important creative relationships in my life.” Miss You Like Hell tells the story of a mother and daughter trying to work out their relationship while the mother faces deportation. Political changes over the years haven’t affected the story they were telling, but they did cause Hudes and McKeown to wonder how the musical would be received. “There were points when we thought our story would be irrelevant because things were getting better for undocumented people in our country,” McKeown says. “Now, sadly, we’re in a position where it might be too relevant because things are going to get worse for people. Instead of a cautionary tale, we may have a prediction of a more common future.”

McKeown’s music has consistently had a progressive edge, but rather than write from a philosophical or political position, her songs start at a personal level. “You see the story and you have a reaction to it,” she says. “That reaction on a human, heart level—then you form a policy decision.” She hopes that Miss You Like Hell and other projects she is a part of work as human stories and not simply part of someone’s Facebook outrage churn. “It’s a three-dimensional story in front of you in a room. Whether that changes hearts and minds—we’ll find out. I think when you show a story like that, if you told it well enough, there’s one reaction to it.”

For Miss You Like Hell, one of the challenges for McKeown was to tell a story that required a cross-cultural imagination. It helped the Hudes’ mother and stepfather are Puerto Rican, and the star of the musical, Daphne Rubin-Vega, is Honduran. The story dictated much of her writing, but others let her know when she missed emotional or interpersonal details that were culture-specific. “The way that a certain character prays or swears—details that are ordinary but tell you about a person—we’ve gotten feedback on that and we’ve changed it,” she says.

The project came to McKeown out of nowhere. Hudes emailed her website and said that after hearing McKeown’s 2009 album Hundreds of Lions, she thought McKeown had a bead on the sound she heard in her head for the music in Miss You Like Hell. Nothing had happened to McKeown before, and she was feeling restless, ready and looking to do something new. She released her first album in 1999, and more than a decade of uncertain finances and endless road work for most of the money that came in exhausted her. “That crossed into a sort of spiritual malaise—Why am I doing this?—so I was looking for someone to join me in my solitary road,” she says. Less existentially, she was also someone up for adventure and someone who likes theater. Her 2011 rejection of Christmas music, F*ck That!, emerged from songs she wrote for a friend’s play titled Santacide. 

The freedom from feeling bound by a traditional career narrative allowed McKeown to see this year’s According to Us not as part of a career arc but as collection of songs, performances, and even artwork that she loved. Because the stakes are lowered, that’s the part that matters most. “If people don’t like it or it doesn’t sell or any of those things that are out of my control, I have this really great creative relationship with Quiara and a project that consistently has work to be done on it,” she says. “That buys me another level of freedom, and I like the music that comes out of that freedom.” 

It’s easy to hear why. Miss You Like Hell seems to scratch McKeown’s need for emotionally and narratively linear songs and freed her up for smaller, more elliptical songs that reflect people and thoughts in quick sketches and unpredictable ways. “The Queer Gospel” title promises a broad sing-along for the LGBTQ community, but she scales it down to her personal anthem du jour. “I believe in the tradition of lipstick / and the sanctity of electric guitar,” she sings, but there’s no reason to think while she’s singing it that the details won’t be very different this time next year. 

You can hear her interest in the musical trappings of spirituality, but she bends them to her agnostic purposes. The call and response vocals over percussion evoke not just gospel but southern gospel on “Where Did I Go,” but God is nowhere to be found in the song. “Sugar in a Pie” sounds like familiar folk love song, but on an EP with “The Queer Gospel,” you can’t help but re-gender in your head the Appalachian folk song stories it evokes.

According to Us didn’t specifically start as an EP, but since most of McKeown’s creative energy was going to Miss You Like Hell, she knew she didn’t have an album’s worth of material. Since she wasn’t sure she had an album’s worth of money either, that worked out. “I had six that were kind of good, and I spent time making them good,” she says. Once she was finished, she was happy with the way they hung together. “The six song EP thing is as clear a thought to me as an album.”

Clear thought doesn’t mean linear, though. McKeown has long been a fan of rock music’s love of impressionistic lyrics, and According to Us indulges that affection, though less than on previous records. “I love the fact that anywhere from three-quarter of the time to all of the time, you don’t know what the singer is talking about,” she says. “I think that’s fantastic. That gives me room to find my own meaning in it, and I may have been doing minute data processing all day long, and please give me two and a half minutes where I don’t know what’s going on.” 

The songs for Miss You Like Hell demand linear thought—“You can’t get away for a second in a musical saying something that people don’t know what it means”—so on her own, McKeown let some of her more elliptical moments be. “There’s a really great incoherent pleasure in rock ’n’ roll.”