Desiree Montes ‘leads with sincerity’ as Billie Holiday

Orlando singer and actress Desiree Montes has channeled Billie Holiday in six productions of Lady Day at Emerson’s Bar & Grill, playwright Lanie Robertson’s tactile recreation of one of the legendary jazz and swing vocalist’s last-ever performances.

She’ll don the white, strapless gown and tuck a gardenia behind her left ear once again for Tampa’s Stageworks Theatre, which is opening Lady Day – a one-woman performance, save for Holiday’s mute, piano-playing accompanist – Friday, with a preview performance Thursday.

Holiday, who died in 1959 at age 44, was a remarkably supple singer, with phrasing and textures no one could imitate. She was a songwriter, too, who gave the world “God Bless the Child,” “Lover Man” and the bitter, haunting “Strange Fruit,” which metaphorically described a lynching.

“I have always seen her as a pioneer of the Civil Rights Movement, before there was ever a Civil Rights Movement,” said Montes. “And I think that comes with a lot of strength.

“She had to be strong from the time she was a child, because she was being raised by a child, in pretty poor circumstances.”

Holiday, who endured a desperately poor childhood of abuse and neglect, was ultimately felled by her addictions to drugs and alcohol. And as she – played by Desiree Montes – explains to the audience in Lady Day, the years in between were no picnic, either.

Desiree Montes.

Taking on the role of one of music’s most tragic figures, for the seventh time, is a challenge Montes is ready for.

“I’ve done this show since 2014, and I’ve grown significantly since then,” she explained. “I’ve dealt with major loss. I’ve been around people who have had alcohol and drug addiction. There are different things I can tie into to be as relatable to her as possible.”

In the moment, she adds, Billie takes over. “I like to sit with her at least 30 minutes to an hour before the show starts, trying to get into the mindset of what it was like for her to be back at this place in Philadelphia. It was very traumatic for her at this stage in her life, against her better judgement. And the things she must be reliving.”

Before beginning each new journey into Holiday’s wounded psyche, Montes reads more, learns more. Tunes her performance just a little bit in a new direction.

“One of the things that I always try to tap into before every production is just to lead with sincerity,” she said.

She is not, Montes insisted, merely doing an impression. “I actually grew up listening to Billie Holiday, so channeling her singing voice felt a lot more ‘home’ to me than maybe trying to find her speaking voice. Especially when I first did this role; there wasn’t a whole lot of live interviews that you could find, where you could hear her speaking voice.

“Especially her in her comfort zone. She had a pretty foul mouth, and she would speak with a certain timbre and cadence and energy when she was around people that she was more comfortable with.”

Montes was, however, to find the common ground she shared with her subject.

“I’m sure there were plenty of times where she likely didn’t feel it, or didn’t necessarily want to be there,” she said. “Not that my life mirrors Billie’s, or that I’ve endured the same kinds of tragedies by any stretch – but I’m always viewed as the strong one, and I know that there’s times when I don’t want to be. I don’t want to always feel like I need to be the strong one, I just want to live. I just want to do the things that I enjoy, and be around the people I enjoy being around.

“I would consider her to be significantly stronger than most people that were walking around in that era. I also sense a huge vulnerability in her, and a desire just to be loved, and just to be. And do the thing that she wanted to do the most.

“And unfortunately, she was not left alone to do that.”

For Stageworks showtimes and tickets, visit this link.