She’s 1, 2, 5 times a ‘Lady’: Desiree Montes is back in Billie Holiday’s shoes
Desiree Montes was “terrified” the first time she portrayed legendary singer Billie Holiday. That was back in 2014. Fast-forward a decade, and now Montes is set to play Holiday a fifth time in Theater West End‘s production of “Lady Day at Emerson’s Bar & Grill.” The Sanford theater’s latest production opens Sept. 13.
“Audiences expect to just come see someone in a pretty dress singing Billie’s songs for 90 minutes, but what you get to witness is much more,” says Montes of the play. “It is a very intimate, personal look into the spirit of this beautifully complex individual, as told by her in some of the last days of her life, and what a privilege that is for all of us.”
Holiday was certainly complex. A supreme talent who had a lasting effect on singing and musical styles, she served time in prison before performing sold-out shows at Carnegie Hall. She hit the top of the charts on multiple occasions but also faced legal troubles and suffered racial discrimination. She died in 1959 of heart failure after years of alcohol and drug abuse when she was only 44.
The first time Montes stepped into her shoes was for a 2014 co-production of “Lady Day at Emerson’s Bar & Grill” by Greater Orlando Actors Theatre and Theatre Downtown. Paul Casta?eda, Montes’ “good friend and chosen brother,” directed.
“He entrusted me in the role, and though I was terrified to take on portraying someone I care so deeply about, I was honored and am forever grateful for his faith in me,” she says. Montes received praise from me for her “strong, focused performance” and her “careful attention to phrasing” that let her “conjure the spirit” of Holiday.
Little did Montes know that, in the years to come, she would return to the role time and time again.
“I never approach this piece in the same way twice,” she says. “I strive to always continue learning more about Billie: Her story, her nuances, her mannerisms. I always dig deeper, research and learn more.”
With age, the actor has found more to dig into.
“Versus back in 2014, I bring much more life experience to this role,” Montes says. “I am not too far from the age she was when she left us and have suffered much personal loss over the years up to more recent months, have been witness to debilitating addiction, and have experienced declining health.”
The Theater West End production will be directed by Ay?? Jeriah Demps, whose long list of credits includes directing “Appropriate” for the Ensemble Company in Oviedo and starring in “The Rocky Horror Show” at Theater West End, as well as in “Sweeney Todd” — where he starred alongside Montes.
“Just as I do, Ay?? has an immense amount of love and respect for Billie,” Montes says. “It’s of the utmost importance to me that the team I work with respects not just the work, but more important, the woman behind the work.”
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Montes is excited to be working with Demps on the show, which was written by Lanie Robertson and premiered in 1986.
“Ay?? has a brilliant mind; she is nuanced, insightful, a singer with deep musical roots, and a member of the queer Black community. She has a lens that other directors may not, and will not only take care of Billie and her legacy but prioritize taking care of me.”
The show’s gritty and weighty material can take a toll, Montes says.
“To know that I have a team who is looking out for me, to know I don’t have to shoulder all of that weight alone means more to me than most will understand,” she says. “The prep, the performance, the cooldown, the role … can be very isolating — and can really mess with your mindset if you don’t take great care.”
Montes’ relationship with Holiday goes back long before she started playing her onstage.
“I grew up listening to and admiring Billie,” she says. “There was no one like her, and her vocal style was so specific, so intentional and so unique.”
In fact, Montes says, she owes her career today to Holiday’s ability to convey her depth of feeling through music. It inspired her to seek to connect with and affect people through performing.
“I didn’t realize it at the time,” she says, “but she was one of my first masterclasses in storytelling.”
As a Black woman, Montes says she’s in awe of the racial trailblazing done by Holiday, who endured bigotry throughout her life.
“To know she was, whether she realized it or not, through her art essentially leading the beginning of the civil rights movement before there was one, and doing so alone, with little to no support and the government on her heels, breaks my heart,” Montes says. “The connection I have to her life story and the strong desire to make sure I am using my platform as she did to spread the importance of the steps she took, the bravery she showed, the resilience she had, to step on stage and fight for her right to do what she loved to do in the face of discrimination and adversity … it’s important to me.”
That feeling of “Lady Day” having importance beyond its entertainment value is what keeps her coming back to Billie.
“It is more than a role in a show,” she says. “It is an honoring of a legend. A jazz legend. A female legend. A Black legend. A civil-rights legend.”
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‘Lady Day at Emerson’s Bar & Grill’
What: A play with music performed as a concert by Billie Holiday
Where: Theater West End, 115 W. 1st St. in Sanford
When: Sept. 13-29
Cost: $25 and up
Info: theaterwestend.com