Andra Day Opens Up About Mental Health, Family and Coming Back from Billie Holiday in Candid Interview (Exclusive)

The Grammy and Emmy winner tells PEOPLE about her new album, 'Cassandra (cherith),' recovering from immersive acting and plans to start a family

• Andra Day's new album, Cassandra (cherith), is out now via Warner Records

• The project arrives after the R&B star earned Grammy and Golden Globe Awards for her immersive portrayal of Billie Holiday in 2021’s The United States vs. Billie Holiday, which was difficult for her to recover from

• The singer and actress has since placed focus on her mental health and hopes to start a family soon

Andra Day has lived quite a bit of life in the eight-plus years that’ve passed since her last album, Cheers to the Fall, was released in 2015 — from portraying Billie Holiday in 2021’s The United States vs. Billie Holiday to winning Grammy, Emmy and Golden Globe Awards and performing at the 2024 Super Bowl. 

More importantly, however, Day learned a whole lot more about herself. The R&B singer and actress released her new album, Cassandra (cherith), on May 10, a 16-track project chronicling her ongoing journey of self-discovery — starting with its title, which marks a reclamation of Day’s birth name, Cassandra Monique Batie.

“I was just uncomfortable in myself, in my own skin,” the 39-year-old “Rise Up” musician, whose stage moniker combines her birth name with Holiday’s “Lady Day” nickname, tells PEOPLE. “Then, I got to know what my name meant, ‘Truth teller, encourager of men,’ and I realized showing up as me is perfectly fine — more than fine. It can actually be encouraging or a blessing to people.”

Growing up in San Diego, Day often felt introducing herself as Cassandra felt “phony and weird” and chose to perform under a stage name in order to create “a slight separation.” The choice suited her for a while, as she was discovered by Stevie Wonder and his ex-wife, Kai Millard, in 2011 and signed to Warner Records a couple years later before releasing the retro-influenced Cheers to the Fall to massive success.

Pretty quickly, Day went back into the studio with what seemed like a clear idea for her next project: “an empowerment album that’s a little more cold-blooded, a little more in your face, talking about the system.” After getting started, she auditioned to play Holiday in 2017, landed the role a year later and transformed herself into the “Strange Fruit” singer physically and emotionally. 

Stepping into Holiday’s shoes took a toll on Day’s wellbeing, as she began drinking, smoking and looking at the world through Holiday’s eyes. “There's confidence I got from her. There's definitely toxic traits I got from her as well too, especially when it comes to relationships,” admits the performer, who split from a romantic partner while wrapped up in the role. “I realized I had to kind of just get real with myself and be like, ‘Wow, I've not been making good decisions.’”

Related: Andra Day on Critical Reaction to Her 2024 Super Bowl Performance: 'I Have Peace' (Exclusive)

Throughout the making of The United States vs. Billie Holiday, Day found herself unable to work on music of her own. Following the film’s press cycle and fruitful awards season, it was time to resume working on her album — but difficult to find herself again. “I wish I would have known, though, before going in, that they actually have therapists to help you undo characters,” she says. “I have a therapist now.”

As Day tried to reconnect with herself, she continued to make songs, then paused as she landed film roles in Exhibiting Forgiveness and The Deliverance. “Diving into other projects would help me to shed the character a little bit. I would pick up some of the new character, but I shed a little more of the old character,” she reflects.

Ultimately, Day realize she needed to stop seeking out the person she was before playing Holiday and embrace a new version of herself.

“As soon as I just started writing from a place of what I was experiencing — love, loss, my own personal growth — that's when things started to flow. So it just became a super, super personal album, and that's why I named it Cassandra,” explains Day. “I have this weird history with my name and the meaning of it, but also it was the only way to describe the album. It just felt like, ‘This is me in the last decade.’”

Cassandra (cherith) also features vulnerable explorations of Day’s mental health journey. She was diagnosed with ADHD as a child, but her mom, author D. A. Batie, avoided giving her medication in hopes of letting her mind develop freely. Through more recent visits with therapists and psychologists, she learned she was still experiencing ADHD symptoms as an adult.

“It's very, very hard to focus, very hard to be on time. And then you get hyper focused because you're chasing a dopamine rush. I think it has presented itself in my relationships and at work and everything,” says Day, who wrote about her mental health experience, specifically as a Black woman in the United States, on the new album track “Heavy on My Mind.”

“I'm still in the process of discovery, which is crazy to say at my age because you feel like you should have it under control. But I had no idea,” she explains, noting that the diagnosis “has actually helped me to stop telling myself I'm this horrible person who's so broken and can't do anything, and I'm a failure, and waking up feeling so heavy sometimes, because I'm like, ‘You are just neurodivergent, you are just wired differently. That's OK.’”

While Day is admittedly still figuring out the next steps of her mental health journey, “There’s something about the process that helps already,” she says. “Everything feels less hopeless.” 

Rather than only looking back on the past few years of her life, Day is now able to think about the future. Despite being single, she’s now beginning to think about the prospect of motherhood. 

Related: How Andra Day's Role in Billie Holiday Biopic Pushed Her to Explore Freezing Her Eggs

“I think I'm going to just pop out these babies and do it by myself. I got God and my mama. I'm good,” quips the star, who plans to freeze her eggs within the next year. “I'd love to be in love, I'd love to be married, I'd love to have a family, all the things. But I’m not going to let that stop me.”

Day’s current, grounded perspective has also impacted her outlook on success in regards to Cassandra (cherith). Her last album earned three Grammy nominations and spawned a smash hit, so she naturally hopes to reach the same level this time around. “But I will tell you, I made an album that I really love,” she says.

“I try not to be so nihilistic, like, ‘Oh my God, if this doesn't go well everything is over.’ No, no. You just make more music, put more music out and just keep doing it,” continues the vocalist. “I want both. I want people to like it, but I also just want to make sure I'm free of placing my personal value on that.”

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Currently halfway to EGOT status, Day has come a long way from when she was discovered by Millard and Wonder. Since then, however, she’s kept in touch with Wonder and even performed at the same gigs as the “Superstition” icon, who’s showed her that even the most legendary musicians have to put in work to stay creative and ambitious.

“We were having brunch one time, and he wanted to play me these songs that he was working on. His mentality was so like, ‘I just really want to know if you like it. Do you think people will like it?’ And I'm like, ‘Why would you ask me anything?’ Like, ‘Bro, you have done this,’” recalls Day. “But I think there's something so special about keeping that hunger and keeping that drive.”

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