As its title might indicate, queer country band Karen & the Sorrows' new third album, Guaranteed Broken Heart, is chock full of sad songs. Both frontwoman Pittelman and the band itself were going through a number of personal and professional tumult at the time they were writing and recording the project, especially as the Sorrows' lineup changed after the release of their 2017 album The Narrow Place.

Pittelman, a self-professed lover of sad songs and '90s country, used that upheaval to process her emotions, broaden her horizons and produce on Guaranteed Broken Heart truly beautiful songs that take both lyrical and sonic influence from country music's most shimmering compositions. The new record is out on Friday (Oct. 18).

Ahead of Guaranteed Broken Heart's release, The Boot sat down to talk with Pittelman about her band's new record, sad country classics and the genre's undeniable obsession with expressing sadness in the most beautiful, elegant ways imaginable.

Courtesy of Baby Robot Media

When you sat down to write this record, what was your frame of mind like? What kind of emotional place were you in?

I was thinking a lot about loss, as you can probably tell just from listening. I was thinking about loss and love and grief and the way all of those things swirl together. A lot of things were ending or changing in my life around that same time, and I think all of that came out in the music.

Did you find it difficult to write these songs, or was it more emotionally cathartic?

Definitely cathartic. I feel that way about music a lot, especially when stuff is happening in my life that makes it hard to find the words to describe. I do a lot of different types of writing, but the deepest feelings always want to come out as music. When I'm in the process of writing the songs, I'm so happy, even though I tend toward writing sadder songs. I just love working on songs and bringing them to other musicians who help me bring them to life. There's so much joy in that for me, even if I'm singing about the saddest things.

After you released The Narrow Place in 2017, Karen & the Sorrows' lineup changed significantly. How are those changes reflected in the music?

I wanted to go in some new directions, and my old bandmates were really supportive of that. The way that Guaranteed Broken Heart sounds has its origins in me working with all different kinds of new musicians and trying a lot of things that I wasn't able to try before. Half of the songs on this album were recorded with a string band, and that was a totally new experience for me. It was really exciting, but scary. I loved having that freedom to bring together all the musicians I wanted and bring the sounds that I heard in my head to life.

You've previously described your sound as "'90s country through the lens of Neil Young." How did that combination come together in your head?

A lot of the time with music, what's inside your heart just comes out and mixes together in all sorts of weird ways, and that's part of how this came together. Neil Young has always been a touchstone for me in my music, and he's always there. I love and obsess over '90s country arrangements and how shimmering and glistening and perfect they can be. A lot of people are dismissive of that time in music because it feels so polished, but the polish doesn't take away from the emotional power of those songs.

'90s country and Neil Young are wildly different. How did you make these two very disparate sounds work together?

For me, Neil Young is just this deep howl in your core that comes when he plays one of those one-note solos and it feels so right. He's tapping into this core pain inside me, and I just want to hear that one note go on forever. It's completely opposite of the spectrum because he's not going for that '90s studio polish at all, but he's trying to get to those same powerful feelings as these classic '90s country songs. The rawness and intensity of Neil Young's emotion comes together with the things that I loved about '90s country production.

"The thing that matters most to me is to create something that's true to what I'm hearing in my head and what sounds beautiful. I want those songs to get out into the world so people hear them."

What are some of the essential songs you looked to as inspiration while writing and producing Guaranteed Broken Heart?

I spent a lot of time obsessing over "Choices" by George Jones. I love Tim McGraw; his song "Just to See You Smile" makes me cry every time I hear it. Same for "You Don't Even Know Who I Am" by Patty Loveless -- that song just f--king destroys me. These are all really good examples of what I'm trying to get at with this record. There is so much suffering in these songs, but they're really elegant in their suffering.

Is it confounding to you that, even though these songs would fit in perfectly with any of the songs you've mentioned, they would've never ended up on '90s country radio? Or even now?

It's always been true that my influences and where I am welcome occupy two different spaces. It's too hard, especially when you're an independent artist, to do all this stuff unless you're making music that you believe in. The thing that matters most to me is to create something that's true to what I'm hearing in my head and what sounds beautiful. I want those songs to get out into the world so people hear them. And then there's the business side of things and what that machine wants and who they promote and what their values are, and I can see how I don't fit that. I relish being independent, but I'd also love for as many people to hear my music as possible.

Do you feel excluded from the "country music" label, at least the way the genre is defined in the mainstream sense right now?

I see who I am, and, in many ways, just in terms of identity, who I am doesn't exactly fit what the industry wants. We're in a moment where all of us are trying to push the industry to broaden their horizons, but it hasn't gone very far. At this point, we're saying, "Maybe you could play women on the radio." It almost feels like a regression moment. It's bizarre to me that we're having that fight when I think country music is all about women singing their hearts out. There's no country music without Patsy Cline or Maybelle Carter.

Women being on the radio in an equitable way is still a far cry from centering people of color, centering queer people or trans people, or talking about political values that aren't conservative. I'm very bad about keeping my mouth shut on those things, and I know that probably doesn't help me with the industry.

"All I'm doing is following the rules of country music. I would be failing at country music if I wasn't telling the truth about my life."

What do you hope that people who hear your record and know nothing about queer country will take away from it?

I just hope they think the music is good. Everybody is capable of empathy, and that works in all directions. If you're not used to seeing yourself represented in music or culture, you can still find parts of yourself in others. Kenny Rogers' life has very little to do with mine, but I can still listen to "Love Will Turn You Around" a hundred times because I love it so much. Someone listening to Guaranteed Broken Heart may have very little in common with me, but if I write a good song, they'll want to listen to it. In the ideal world, where we can connect through art and music, that starts to build bonds between us all as humans.

Have you experienced any of those bonds with new fans who've stumbled across your music?

One time, somebody wrote a comment on one of my videos that was like, "I really love this song, this video, but I don't need to know about your sexual identity." I wrote back that I hear that, but I'm making country music. Country music is all about telling stories about your life. We have this genre where people are talking about the worst suffering they've ever been in. If we could really listen to each other about the worst suffering that we've all been through, that's enormously powerful.

All I'm doing is following the rules of country music. I would be failing at country music if I wasn't telling the truth about my life.

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