Kaina Castillo Credit: Photo by DDesigns

On Sunday, March 24, singer-songwriter Kaina Castillo spent the day with her parents at her childhood home in Irving Park, working on a music video for the song “Green.” The director, singer-rapper Jean Deaux, wanted to film what Kaina considered a perfect day: spending time with her family and friends and kicking back with drinks and a good meal.

When the small crew arrived at Kaina’s parents’ place around 7 AM for the shoot, her mother, Maritza, had prepared orange juice and coffee for them. “I never realized how hard it is to make a video,” Maritza says. “It’s amazing that you work the whole day for a few minutes. But I was so happy, everybody was so nice—like a family.” Kaina’s father, Rene, turned 54 years old that same day, so in a way the shoot doubled as a birthday party for him.

Kaina’s dream day didn’t include work, but there was lots of it to be done. Her friends and family—including her brother and her godmother—helped out to make sure the shoot stayed on track. “We were trying to hang up a clothing line, and my mom was like, ‘I did this in Venezuela, and you guys are not doing it right,'” Kaina says. “She took matters into her own hands and nailed shit to the wall, ’cause me and Jean Deaux were trying to tape things.”

Maritza also cooked for the whole cast and crew—roughly 20 people. The video’s opening shots include close-ups of her hands working dough for the five dozen arepas she made that day. Kaina is definitely the star, but her loved ones give the video its warmth and intimacy. Nothing onscreen tells you that you’re looking at her parents, for instance, or at her closest colleagues (including rapper, singer, and producer Sen Morimoto), but it’s obvious that these people are special to her.

In April, the Fader premiered the video for “Green,” which Kaina had chosen as the first single from her debut full-length, Next to the Sun. The album comes out Friday through Sooper Records, an artist-run label owned by Morimoto, Nnamdi Ogbonnaya, and Glenn Curran. Kaina, 23, has been a fixture on Chicago’s overlapping hip-hop and soul scenes the past four years, both onstage and behind the scenes; she freelances in show programming and production, and last year she hit the road as a tour manager with Chicago R&B darling Ravyn Lenae. Kaina’s star has begun to rise in part thanks to collaborations with friends—she’s among the three guest vocalists on Saba’s Care for Me, one of 2018’s best albums.

Kaina album-release party for Next to the Sun

Food, copies of the album, and other merch will be for sale. No live performances. Fri 7/12, 6-11 PM, Sat 7/13, 1-9 PM, Mama Castillo pop-up restaurant, 3056 N. Lincoln, free, all ages

Kaina, Kara Jackson, Luna Luna, Sen Morimoto, Kahekili

Sun 7/14, 6:30 PM, Lincoln Hall, 2424 N. Lincoln, $15, all ages

Kaina has a powerful, earthy voice that she uses with an inviting restraint. Her nuanced, earnest singing immediately charmed Chris Swanson, who co-owns Indiana indie label Secretly Canadian as well as its distributor, Secretly Distribution, which handles Sooper’s releases. He first saw Kaina in late 2017, when he drove to Chicago for a Morimoto show at Soho House and she was also on the bill. “I was just blown away by her voice,” Swanson says. “It immediately resonated. I was like, ‘She’s a star.'”

Kaina had yet to sign with Sooper in late 2018, when Secretly Distribution struck its deal with the label, but Swanson sees her as part of what makes it special. “With that core of artists—Nnamdi, Sen, and Kaina—it feels like that’s a nucleus for making a really strong label,” he says. He followed her from afar, listening to her EP 4u (which she self-released in March 2018) and her subsequent singles. “I felt like she was continuing to tell a really exciting story,” Swanson says.

On Next to the Sun, Kaina delves into her experiences as a first-generation American, an approach she drives home by involving her family in the “Green” video. “I am the beginning of a literal family in the U.S.,” Kaina says. “We don’t have a lot of space we own for ourselves in the U.S. Building a video like this, it’s cool to have a piece of art that’s like, if there’s any legacy, it’s this. We all built this.”

“You with your walls, you’re so proud / You stay so happy keeping all us out / You like to keep this place so empty / Look how these brown hands cook all your meals / But mama says you want us all to disappear / You like to keep this place so empty”—Kaina, “House”

Kaina wrote the Next to the Sun track “House” as a high school student at Lane Tech. Even after she graduated in 2014, she kept it under wraps for several years, refraining from recording or performing it. “I didn’t feel comfortable talking about the world and immigration, especially because it felt so close to my heart and close to a lot of families that I see around me,” she says. “I didn’t feel comfortable until now to release it, because it was really personal.”

Maritza emigrated from Caracas, Venezuela, in the mid-80s at the invitation of Kaina’s godmother, Fanny Gimenez, who’d just had a baby in Chicago and asked Maritza to help with child care. Gimenez works for the Venezuelan consulate here, and through her job she introduced Maritza to prominent Venezuelans in town—including Ozzie Guillén and Wilson Álvarez from the White Sox. When the ballplayers’ families needed help looking after children or taking care of chores, they turned to Maritza.

Photo by Mercedes Zapata

Kaina’s father, Rene, came to Chicago from Guatemala in 1991, staying with an aunt who already lived here till he got settled. Rene and Maritza met in 1995 through mutual friends. They liked to hit the town together, and Kaina says they used to go to Latin clubs and dance till 5 AM. “Then I came and ruined their fucking life,” she says. “They were at all the Jordan games—they were going to all that shit.” Kaina was born January 22, 1996, just before the Bulls started their second threepeat.

“I always tell Kaina, ‘I think you were born with music,'” Maritza says. “That first Christmas, I got a doll for her—she took the doll out from the box, she put the doll away, she got the box, and she started playing the box like a drum.”

Kaina got her first meaningful taste of performing at an Audubon Elementary School pageant. “I remember singing this part, and these kids turned around and gave me weird faces,” she says. “Looking back, I’m like, ‘Oh, maybe I could sing.'”

By age nine she knew she wanted to sing, but she says she was too shy. That year, when she found out about the Happiness Club, a performing-arts extracurricular aimed at grade-schoolers, she auditioned as a dancer. “That was all my training,” she says. “It was my training as a human being. It was my training as a performer when I didn’t even know it.”

The Next to the Sun song “Joei” opens with a recording of Joei Simone Langford, daughter of Happiness Club artistic director Tanji Harper, talking about what it means to have a crush. Langford is nine—the same age Kaina was when she first met Harper. “Tanji became like a second mom,” Kaina says.

The Happiness Club works with kids across the city, mainly from neighborhoods short on resources for young people, including Bronzeville, Chatham, Englewood, and Pilsen. Students get dance and vocal training and assistance with choreographing and writing their own shows, which are intended for youth audiences. Kaina performed for children throughout Chicago.

“I got to come across a lot of different kinds of kids in neighborhoods,” she says. “I don’t have a big family—I feel like I could have easily been whitewashed and assimilated into the country. But because of a group like this, I really had a lot of opportunity to see a bunch of things, and even go outside of Chicago for the first time.” During the ten years or so that Kaina participated in the Happiness Club, she performed twice at the Obama White House and appeared in 2010 on Lollapalooza’s Kidzapalooza stage.

  • Kaina sings with the Happiness Club at the White House Easter Egg Roll in March 2016.

Late in her tenure with the Happiness Club, Kaina switched roles, but she spent most of that decade dancing. “I got really fucking good,” she says. “I quit dancing around 16, ’cause I was like, ‘I don’t want to do this anymore,’ and ended up singing and writing songs for the group.” By then she was a sophomore at Lane Tech and had started going to other people’s shows—she never skipped a date by the O’My’s or Saba. “One day, all of those people were like, ‘I see you at every single show—who are you?'” she recalls.

In 2014 Kaina formed her first band, a soul-funk combo called the Loop. The summer after she graduated, they played a noon set at Postock, a Wisconsin festival launched in 2008 as a graduation party for a small group of Chicago musicians. Despite the Loop’s early slot, O’My’s front man Maceo Haymes and Ohmme singer-guitarist Macie Stewart were in the crowd. “I remember it just being so bad—it was so bad,” Kaina says. “Maceo’s always like, ‘No, you had a great voice then too.'”

The Loop sputtered out once people started leaving for college that fall. Kaina went to DePaul to study public relations and advertising, but she was getting more out of two internships she’d been working since high school. The first was with Mariah Neuroth, director of production for Young Chicago Authors, who also managed Noname and the O’My’s. Neuroth introduced Kaina to Sharod Smith, manager of soul-pop duo M&O, aka Jamila Woods and Owen Hill, and she started interning for him too. Kaina and Smith bonded when she stage-managed M&O’s record-release show at Double Door in April 2014.

“The folks who are running the show have a responsibility to be calm,” Smith says. “I’m just naturally calm, and she was the other calm person that was able to navigate the chaos. That’s a skill that not a lot of people actually have—she’s able to remain calm in such chaotic environments, which is why she’s worked for damn near everybody in the city.”

Photo by DDesigns

Within a couple years, Kaina had a full Rolodex of people eager to hire her as a freelance manager for live events. By the time she dropped out of college in September 2016, early in her junior year, she’d used those jobs to build up a financial cushion.

“DePaul was my first experience really feeling like I didn’t belong somewhere in my own city—it was really disorienting,” Kaina says. “I was the only brown kid in my PR and ad classes. It was really tough for me to get into my first years of adulthood and start to notice things like microaggressions. Like, Lane Tech and my elementary school were really diverse, and the Happiness Club was obviously culturally enriching. But getting to DePaul, I didn’t have any friends.”

Kaina met Sen Morimoto at a Hungry Brain show in November 2016, a few weeks after she dropped out. Morimoto was there to see his friend Nnamdi Ogbonnaya, and Kaina was also on the bill. Since then they’ve become best friends, and on the Next to the Sun single “Could Be a Curse” they trade verses in English and in their second languages, Spanish and Japanese.

That fall she had to confront her difficult decision to leave school as well as the disillusioning consequences of pursuing music as a career, not just as a passion. She’d cut back on her involvement with the Happiness Club, and by the end of 2016 she’d quit entirely. She’d also started working with Eddie and Iz Burns, 18-year-old twin brothers who perform and record as the Burns Twins. Kaina, the twins, and producer Bedows released an EP called Sweet Asl in August 2016, which got a Fake Shore Drive plug. “It just blew up,” Kaina says. The song “La Luna” has nearly two million plays on Spotify—a big number for the debut of a young act that never toured.

Navigating the business side of music soured Kaina, though. “This is crazy, these are my diary entries—now I have to think about music as a business as opposed to something that liberates me. It feels like I am just something to make a profit off of now,” she says. “It felt really shitty. But Sen really helped me through that slump.”

Morimoto loved Kaina’s Hungry Brain performance. “It was one of my favorite sets I’ve ever seen,” he says. Soon he reached out to her to join the band he was putting together for his Tomorrow Never Knows set at Lincoln Hall in January 2017. She said yes before she’d heard any of his music. As they hung out more, they developed an informal routine. “On the weekends, we would go see something—go to a garden or go to a temple—and then we would go work on some music,” Morimoto says.

Kaina had handfuls of unfinished demos, but no motivation to finish them. “Sen was like, ‘You should finish this. You need to finish this,'” she says. Kaina eventually wrapped up three songs, recording with Morimoto during lengthy hangout sessions at his apartment or hers. She released them in March 2018 as the 4u EP, and within weeks she’d also appeared on three key Chicago releases: Saba’s Care for Me, Morimoto’s Cannonball!, and Joseph Chilliams‘s EP The Plastics.

Kaina got more exposure, but once again she felt her momentum falter. She’d grown frustrated with what she saw as the one-sided emotional content of her material. “I was having a really hard time being honest about the kind of stuff I wanted to write,” she says. “My previous music, it’s all really sweet, loving, and full of positivity, and that’s great. But I got to a place where I was like, ‘It’s not sustainable to only show that you are a happy person all the time—it’s just not true.'”

Her desire to be more transparent meant engaging with parts of herself she hadn’t addressed in her music, including her family history. Her Spanish lyrics on “Could Be a Curse” are her first in her parents’ native language. As he had for 4u, Morimoto encouraged Kaina to flesh out her demos, and they produced Next to the Sun together.

When it came time for Kaina to think about how to release the album, Morimoto gingerly suggested Sooper. But he also wanted to encourage his friend to take the route she thought was best for her music. “It was funny to be on both sides of that,” Morimoto says. “If there was a better option or something, I’d be like, ‘You should go for it.’ Or if Sooper feels comfortable. . . . The important thing, really, is that once your album is out, it’s not, like, spoiled by whoever’s running the business side of it.” Sooper felt right to Kaina, though, and she signed with the label in March 2019.

On “Could Be a Curse,” Kaina sings, “Tanto trabajar y no tengo nada,” which she translates as “I’ve worked so hard and still have nothing.” It’s a lyric from the 1979 hit “Tanto Trabajar” by Venezuelan band Billo’s Caracas Boys, which Kaina’s parents played a lot when she was growing up. She says they shared the sentiment in that line—and that they picked up on her reference immediately. “This time, my parents got to see how I’m trying to ingrain all of these pieces into a thing,” Kaina says.

The day Kaina filmed “Green,” she got to experience what it was like for her parents to see her vision in full for the first time. The shoot took over their home for an entire day, but they didn’t mind—in fact they seemed to love feeling like part of what she’d made with her friends. “My mom and I were doing our scene where we are hugging each other, and she turned to me and she just says, ‘Thank you.’ I lost it,” Kaina says. “There’s that last shot where I had just been tearing up, and I was like, ‘Oh man—they got it.'”  v