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They Dated in High School. Now This Duo Makes Sad Soul Music Together.

Danielle Grubb (left) and Delaney Hillan were high school sweethearts. Now they sing sad songs in Cleo.EXPAND
Danielle Grubb (left) and Delaney Hillan were high school sweethearts. Now they sing sad songs in Cleo.
Rebekah Hedges

When Danielle Grubb and Delaney Hillan were in high school, they got in trouble for kissing. The two artists, both Dallas natives, were dating while enrolled at Booker T. Washington ten years ago. One day, a teacher caught them exchanging PDA in the hallway, and started yelling.

“I don’t want to see any of this again,” Hillan recalls the teacher saying. This was common. According to Hillan, same-sex couples were policed differently by at least one teacher at the arts magnet school.

“Straight couples would be doing whatever and no one would be saying anything to them, and the second Danielle and I did anything, the teacher would pull us aside,” she says.

Administrators at Booker T. did not respond to request for comment, but shortly after this incident, Hillan spoke about the experience at a Dallas ISD board meeting. The district would ultimately pass a new anti-bullying policy, a fact that makes Hillan happy.

“I spoke my truth,” she says. “Honestly, I don’t think I would’ve been able to do that if it weren’t for Danielle. Even back then, they were helping me say what I needed to say.”

“I was always impressed by Delaney,” Grubb says. “She’s always had this courage I admire.”

Their romantic relationship didn’t last, but recently, Grubb and Hillan reunited to form Cleo, a self-described soul music duo made up of two “queer, sexy, sad babes with trust issues.” Cleo has released a cover of the Marcy Playground song “Sex and Candy,” and they will release their original debut single “Circles” on Friday. A 10-song EP will follow.

The last decade has been replete with trauma for both artists, but with Cleo, Grubb and Hillan have rekindled a friendship and found catharsis.

“I don’t think anyone else could have brought what Danielle brought out in me,” says Hillan, who never recorded herself singing before this project. “I had been so stagnant for so long, that whenever this door opened up, it gave me release.”

Grubb and Hillan’s lives diverged drastically after high school. Hillan, who was part of the theater cluster at Booker T., moved to Los Angeles. She had dreams of launching an acting career, and worked as a bartender while trying to land gigs.

“The first year I moved there, I thought, ‘Oh shit, I messed up,’” Hillan remembers. “‘This is scary. I’m a child, I don't know anyone.’ But after a while, I built a life. I found some friends. I fell in love.”

Hillan got engaged to a musician, and eventually ditched the acting career for a gig with a stylist that focused on women’s suiting and workwear. On its surface, her life was going well. She would go to work, go out dancing and keep up a smile. Yet most people didn’t know that she was struggling with depression and bipolar disorder.

“People would say, ‘You don’t look happy; are you OK?’” she says. “And I would say, ‘Of course. I’m living in L.A.! Everything is fine.’”

Meanwhile, Grubb was on the opposite coast dealing with their own struggles. The singer, who is non-binary and trans-masculine, uses “they/them” pronouns. They graduated from the State University of New York at Purchase in 2015, and was gradually carving out a music career in New York City. Then a psychotic break landed them in the hospital, and they moved back to Texas to be with family. Hillan wasn’t too far behind. By 2019, her fiance was gone on tour, and Hillan’s struggles with mental health were intensifying.

“I was going through one of my most depressive spouts,” she says. “All creative outlets didn’t make me happy anymore. If I didn’t pick up the pieces, I thought, ‘I won’t make it to 28.’”

Her engagement ended, and she moved home to Dallas to, as she says, "pick up the pieces." The first step was trauma therapy, a process Hillan didn’t relish.

“Therapy can be debilitating,” she says. “Especially if you’re trying to find the right therapist. You’re walking into a new office every few months to explain your trauma, and after a while, you think it’ll never work.”

But slowly, it started to help. It also helped that she was home, surrounded by similar sights and sounds. In her family’s house, the mere sight of books lining a bookcase brought her joy. So did the smell of the detergent her mom uses. So did the people. Hillan started hanging out with Grubb, who always harbored suspicions that Hillan was more talented than she let on.

“I would hear her sing every now and then, and I could tell she was good, even if she thought she was just messing around,” Grubb says.

One day, Grubb asked Hillan if she had ever written a song. Hillan said no. Grubb then asked Hillan if she had ever sang on a record before. Hillan said no.

“I think you can sing,” Grubb told her. “I think you can write. You’re going to come and do it with me.”

It was supposed to be a one-off project, something that Grubb might incorporate into the many musical projects they are constantly creating. Then it became a five-song EP. Soon it was 10 songs.

“We were meeting two to three times a week,” Hillan says. “We were writing alone, we were writing together. We had this very cool arc of tunes that all told their own little story.”

The forthcoming “Circles” is about how Hillan and Grubb met, and how, 10 years later, they’re in a familiar place. Grubb is pushing Hillan to be bolder, braver and louder, and Hillan is reminding Grubb that they, too, can be all of those things.

“I feel like I’ve been walking differently,” Hillan says. “When you have something you’re proud of, it bleeds into every other aspect of your life.”

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By their own admission, most of Cleo’s songs are an eclectic mix of sad and soulful. On the “Sex and Candy” cover, for instance, Hillan’s vocals are persistently dour. Grubb says the upcoming EP will have a similar vibe, and will be full of stories about love, identity and distance. Yet not all of the songs will be sad.

One day, in the middle of a madcap writing session, Grubb turned to Hillan and said, ‘OK, so you’re at a party. What’s the last song you want to hear?”

The pair crafted a tune they call “sexy,” “funky” and “uplifting.” As soon as they played it back, they knew the song, called “Who Got the Aux Cord?” would be the perfect ending to their EP.

“Yeah, that’s good,” Grubb said. “Let’s end it there.”

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