Love you Madly, Holly Woodlawn: A Walk on the Wild Side with Andy Warhol’s Most Fabulous Superstar

A: Love You Madly, Holly Woodlawn is a kaleidoscope of chaos and charisma. If Holly were alive today, what would she think of how you’ve immortalized her?

J: I think she’d be thrilled because, for the most part, it’s a fun and endearing portrayal. My intent was to pay tribute and celebrate the real Holly Woodlawn. She was very endearing. Very funny.  And for a while, I considered her my best friend. But she was also an alcoholic and, at times, a self-absorbed narcissist. In some ways, she’s like a modern-day Norma Desmond with a dash of Baby Jane, Howdy Doody, and Tinkerbelle. And a whole lot of Auntie Mame. She’s a classic underdog, and you can’t help but root for Holly because even though she’s down and out and creating one mess after another, she’s still hilarious and so much fun.

A: Holly’s cabaret performances drew devoted crowds despite her unconventional singing. What do you think made her stage presence so magnetic?

J: I think it was her celebrity as a pop culture curiosity that was more magnetic than her actual stage presence. I remember once Jane Wagner and Lily Tomlin came to see one of Holly’s shows. And I think they came to see Holly because of what she represented. She was part of a magical, lost era in New York…she was part of their youth. They didn’t come to hear her sing because she wasn’t that good of a singer. But they liked her because she was fun and endearing. And I think A Low Life in High Heels helped perpetuate that general appeal. People were drawn to her shows because they wanted to have fun.

A: Your writing captures the absurd and the sublime in vivid detail. How did you balance raw truth with storytelling flair while maintaining Holly’s larger-than-life essence?

J: Well… fuck if I know. Let’s talk raw truth first…I considered Holly my best friend when we were living in Hollywood. Often, when someone found out that Holly was a transgender Andy Warhol superstar, two questions always came up: did she cut it off? And what bathroom does she use? Honestly, of all the things to ask…that’s what they wanted to know! I thought those questions were rude and degrading. But I guess that’s human nature. People were always fixated on her genitalia.  And I was always so taken aback by the question, ‘Did she cut it off?’ so when I decided to clarify that detail, I purposely wrote it in a way that’s irreverent, over-the-top, and in your face. That’s my covert way of saying ‘fuck you’. Not to the readers but to the people we dealt with in the past who thought it was okay to ask those types of stupid questions. Same with the bathroom issue. Boy, did I have fun writing about that!

A: The book captures both Holly and Hollywood’s gritty and glamorous duality. How do you think modern-day Hollywood compares to the grimy, glamorous, and chaotic Hollywood you describe? Do you think modern-day Hollywood has lost its “anything goes” spirit?

J: As far as “anything goes” spirit…. I’m not sure because I’m not involved in Hollywood now. But what I do know is my 1980s Hollywood is gone forever because the people are gone, and the scene is gone. One thing I wanted to do with this book is I wanted to capture that era, and I wanted to celebrate the ‘80s Hollywood Melrose scene. This was a time before everyone got so distracted with their cell phones. And in 1980s Hollywood, there were all these wonderful characters that you’d see around town who are mostly dead now. Back in those days, people who wanted attention took to the streets. They’d put on wacky clothes and hang out at the bus stop. Or they’d cruise through town in a wacky car like Dennis Woodruff or take over billboards like Angelyne. There was one guy who dressed in a black unitard and performed a rollerblade ballet up and down the street. It was so wild and fun! But nowadays, people who crave attention don’t hit the streets. They hit Instagram, Facebook, and OnlyFans. We live in a different world now. But I think it’s just as grimy. Maybe even more chaotic because of all the social media platforms. But it’s not nearly as fun or cool.A: You mention amalgamating secondary characters to avoid jail time. Which real-life personality inspired the most colorful amalgam in the book?

J: I think my favorite is Delores Francine because, like me, she is such a loser when it comes to winning big. She’s a combination of a lot of people, all of whom had such big dreams of making it in Hollywood. But like most of us, she’s stuck in a job she doesn’t really like. And she soothes her disappointments by denigrating others and hoarding fake, illegal Rolex watches.

A: The book has a definite rhythm. Did you consciously structure it like a movie script or song, or did the events dictate the flow?

J: I am so flattered that you recognize this!  And yes… I consciously structured Love You Madly, Holly Woodlawn so it would inspire a film and stage adaptation. When I first wrote the story, there was so much hardship and struggle in the beginning that Holly didn’t make her entrance until page 160. So that was a problem. It was during the rewrite process that the structure was fine-tuned so that Tim Burton would recognize its big screen potential and Andrew Lippa would insist on bringing it to the Broadway stage.

A: Holly caused chaos in both your lives. What’s the wildest challenge you had to deal with?

J: We had so many challenges in the course of our friendship. Keeping our rent paid, putting food on the table… or, in our case, an ironing board. But I think the wildest challenge was the time I convinced an apartment manager to rent a unit to Holly based on her looks and celebrity. She didn’t have good credit. She had an awful rental history. But what she did have was a wonderful press kit with gorgeous photos and fabulous reviews. And I sold him on having a beautiful Andy Warhol superstar living in his building. He was totally blinded by her beauty. And then on the day she showed up to move in, she showed up looking like a man sporting a crewcut with hair on her arms and chest. So that was pretty wild. And then I tripped on a crack in the sidewalk and fell into porn.  And things only got worse.

A: Andy Warhol famously cast “drag queens” because they could “get excited about anything.” If he were alive today, how do you think he’d review your book?

J: When was Holly Woodlawn, Candy Darling, or Jackie Curtis ever a drag queen? To call them that just minimizes who they really were, which is wrong, Mr. Warhol! But if Andy Warhol were alive today and he did pick up a copy of Love You Madly, Holly Woodlawn, I think he’d skim through it until he got to all the dirty parts. He’d love all those gritty, sordid details. And then he’d get so wound up, he’d spin his wig, spank the monkey, and howl at the moon. Might even scoot his butt across the rug like a crazed terrier. Wouldn’t that be a sight to behold?

A: If Holly could see one thing about the world today, what do you think would surprise her?

J: That trans actors and actresses have a strong presence in the mainstream entertainment industry today, and their contributions are valued and revered more than ever.