Hailey Kilgore‘s Tony and Grammy nomination for her turn as Ti Moune in the Broadway revival of Once On This Island did not get into her head and did not make her slow down, not in the least. Laying low as she celebrates her 25th birthday, Kilgore begins the rollout of her new album, ‘Heartbreak and Healing,’ a project in the works since 2019.
On the side of a handful of other lucrative projects, Hailey Kilgore returns where she feels the safest and the most herself – music. Continuing to explore her possibilities as a singer outside of the theatre, her last year’s EP ‘Desire and Devotion‘ was the perfect epitome of finding a sound, going different directions, a sonic abstract to the whole story that will be her new record ‘Heartbreak and Healing.’
Currently, she is finishing the filming for season four of Power Book III: Raising Kanan, a crime drama series about a family drug business set in 1990s South Jamaica, Queens. Kilgore also shares the first preview of what is set to be Hailey Kilgore’s next chapter, which is her new single, ‘Drama Queen.’
In true triple-threat fashion, Hailey Kilgore’s reach goes beyond one arena and resembles artistry and attention to detail of excellence. Multitasking and juggling more commitments at once is all she ever knew: “When I’m not on set, I am focusing on all things album. Rehearsals, shoots, interviews. It’s all so much fun, and I can’t wait for it to continue to ramp up this summer”, she says.
Being critically recognized for a captivating stage presence and performing talent on the magnitude of the Broadway stage is something that one is born with. In possession of this gift, Kilgore does not recall a moment without nurturing the craving for any performance: “Ever since I was a little girl, I have been on stage, even performing for family and friends whenever they came over (whether they wanted to listen or not haha). Singing has always been where I felt the safest and the most myself,” Kilgore shares.
When growing up, our life trajectories are often influenced by the decisions of our parents and teachers. In the case of Hailey Kilgore, both parties had her back 100%. Expressing her complete gratitude, she recalls one of her core memories, which ultimately changed her life and positioned her as an artist at the beginning of her journey: “I don’t know where I would be without my parents. In first grade, my mom and dad got called into a parent-teacher conference. My teacher Ms. Boys told them that I kept taking my bathroom breaks to go into the stall and sing at full volume. She didn’t want to get upset with me or get me in trouble because she loved my voice and wanted to encourage my gift. Thanks to her, my parents put me in choir, piano, and voice lessons. They have truly been supporting me my whole life, and I will always be so grateful for them”.
For someone of Kilgore’s caliber, with Tony and Grammy Award nominations at the age of 25, she does nothing halfway. Once she sets her mind to something, she will not stop until she gets it. This star-levelled attitude sets Hailey Kilgore apart from other rising pop stars. She tells where her unbeatable work ethic comes from: “It comes from my parents again. Without getting too personal, I watched both of them hustle for my sister and me to have beautiful lives. There were times it was really difficult, but no matter what, they were always working and building. My parent also never allowed me to half-ass anything. If I did, I definitely always knew I was gonna hear about it!! I hope I keep getting better and working harder because it’s got me to where I am now, and I don’t intend on slowing down.”
Going back to her teenage years, young Hailey Kilgore intended to audition for her high school’s version of Once On This Island, but destiny knew why this role was delayed for later in her life. Her Tony-nominated performance in the Broadway revival is also why Kilgore believes in full circle moments and in what’s meant to be for you is meant to be for you.
She explains: “The year I was supposed to do OOTI in high school, I actually had to leave public school so I could work as an actor at Portland Center Stage. I was sad that I was missing out on it. What’s crazy is when I was asked to audition for the Broadway production, I initially wasn’t going to go because I was a freshman in college and we weren’t allowed to audition. I’m SO GLAD I changed my mind. Once On This Island changed my LIFE.”
When she received the call to be cast in the Ti Moune role, Kilgore had not intended to make such a career-changing step just yet. She elaborates: “I was taking a break from working professionally to go to college. From the age of nine, I didn’t really have “normal” because I was auditioning, competing in competitions, and working. So, I knew I wanted to take a pause and have a normal college experience… That only lasted for six months.”
Aside from Once On This Island, Hailey Kilgore had success in other roles, starring in the critically acclaimed Respect opposite Jennifer Hudson and the feature Cinnamon as the lead role. From receiving rave reviews at the 2023 Tribeca Film Festival, she also shines on the TV screen as a cast member of Steven Spielberg’s Amazing Stories on Apple and NBC’s The Village and as Jukebox in Starz’s Power Book III: Raising Kanan.
Kilgore was in full swing of establishing herself as an actress, but it wasn’t until someone asked a question that awakened her pushed-aside dream of being a musician. “I always wanted to be a singer and performer! I had kinda put having a music career on the back burner because I was so blessed to be receiving all the acting opportunities. I met Adam Blackstone, who was developing a new musical, and he asked me if I wanted to have a career in music. I immediately said yes, and he has been stuck with me ever since! I started writing seriously in 2019, and I haven’t stopped.”
Gearing up to drop her debut album ‘Heartbreak and Healing,’ Kilgore released her introductory 8-track EP ‘Desire and Devotion,’ which documents her first attempt at coining her sound. Comparing the two, she teases, ‘Heartbreak and Healing’ is a new chapter: “I feel like Desire and Devotion was the perfect appetizer before the album. Because of my theater background, I have always wanted the full story!! So while the EP was me finding my sound and going in different directions. The album is definitely a full story from beginning to end! I still absolutely ADORE Desire and Devotion!! I feel like Heartbreak and Healing is the next chapter”.
The first single, ‘Drama Queen’ serves as a relatable bop blending nostalgic R&B melodies with pop, spelling out the gas lighting and toxic pushback of asking for the bare minimum: “Drama Queen comes pretty early in the album. It highlights the point in a relationship when even when you’re asking for the simplest things to keep a strong foundation for a relationship, and you are constantly getting pushback and being told you are doing too much! Everyone knows that feeling when nothing you do is good enough, but you are so sick with love that you do the most.”
The entirety of ‘Heartbreak and Healing’ has drawn inspiration from Kilgore’s personal experiences and recent relationship and everything that comes with the territory of ‘having your heart broken – facing demons, falling back in love with yourself and enjoying life.’ She reveals more about the album’s writing sessions: “They were surprisingly easier than I thought they would be! I had just gone through a very tumultuous relationship for 2.5 years, so I definitely had a lot to say. I kept the writing team very small to people who are like family to me. JTownsend and Tytewriter are like my big brother and sister. So we would really just sit and talk about life and the healing process. I had a really strong grasp of what I wanted the experience of the album to be, and that really helped.”
As a personal intention for this year, hence the new album title, Hailey Kilgore aims to focus on closing old wounds and rediscovering happiness within herself: “My main intention for this year is to heal… It’s really happening. I went through a really dark time in my life, so I feel like I’m falling in love with myself and my life in a way that I haven’t been in a long time… If ever.”
Courageously taking care of her wellbeing, Hailey Kilgore works to manage her triple-threat stardom. At this point, she has experienced a fair share of the industry; she wishes to share wisdom with other aspiring actors and singers: “Keep your head down and do the work. Observe absolutely everything, but only take what works for you!! Don’t worry about what everyone else is doing because their journey is not yours, and that is a beautiful thing!!! You’ve got this!! Don’t be afraid to fall because you can always get back up. LET’S GOO.”
Hailey Kilgore stands out as an old-fashioned hard-work-pays-off ethic go-getter in the whirlpool of one-hit wonders and new media-polished artists. It is quite refreshing to witness what seems like only the beginning of Hailey Kilgore’s career and see the potential of her abilities in more than one medium. ‘Heartbreak and Healing’ is due to be released on May 3rd.
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Photographer: Xiana Gutierrez “C’est La Zee Photography”
Words: Karolina Kramplova