by Frank Gaimari

Jeff Copeland’s memoir, Love You Madly, Holly Woodlawn, vividly depicts his extraordinary friendship with the iconic transgender actress, set against the vibrant, chaotic backdrop of Hollywood. More than just a biography, the book offers a personal, heartfelt portrayal of Copeland’s journey as a young, ambitious writer navigating the unpredictable highs and lows of the entertainment industry.

Set in the mid-1980s, the story follows Copeland, a Missouri graduate with dreams of becoming a screenwriter, as he encounters the captivating Holly Woodlawn. Once the celebrated star of Andy Warhol’s films, Holly now lives in quiet obscurity, her life a poignant mix of fading glamour and hardship. This chance meeting sparks a friendship that dramatically alters the trajectory of both their lives. Together, they co-author the bestselling autobiography, A Low Life in High Heels, and embark on a whirlwind journey filled with fame, creativity, and personal challenges.

In Love You Madly, Copeland revisits their shared history with humor, honesty, and tenderness. The book recounts not only how they met but also the trials and triumphs of writing their book. From the very first page, Jeff’s writing pulls you in with its vivid storytelling and unflinching exploration of life’s complexities. Woodlawn’s vibrant, larger-than-life personality leaps off the page. At the same time, Copeland weaves his own experiences as a gay man and writer into the narrative.

What makes Love You Madly so compelling is its raw honesty. Copeland doesn’t shy away from the messy realities of their lives — Holly’s struggles with addiction, the challenges of being a transgender woman in a prejudiced world, and his own battles with self-doubt and the pressures of Hollywood.

After reading the book, I had the privilege of speaking with Jeff, who graciously answered my questions about the memoir and his journey with Holly. Here are the questions I asked him.

Frank Gaimari: What do you think Holly Woodlawn’s legacy represents, and how did you aim to capture that in Love You Madly, Holly Woodlawn?

Jeff Copeland: Holly’s greatest impact extends far beyond her contributions to the underground cinema — it lies in her unwavering advocacy for diversity, equity, and inclusion. As a young gay child, Holly faced immense societal pressure to deny her true self. This internal conflict eventually led her to run away from home, embarking on a journey to find authenticity and acceptance. Those years were fraught with hardship — living on the streets and turning to prostitution as a means of survival.

In Love You Madly: Holly Woodlawn, my goal was to fully immerse readers in her journey, capturing the extraordinary resilience and unwavering determination it takes to survive and pursue a better life.

FG: How did you balance staying true to Holly Woodlawn’s real-life story while adding your own creative perspective to the narrative?

JC: As a humorist, I saw this crazy story as a comedy of errors. Holly was genuinely hilarious, and I wanted to capture her essence on the page. The reality we experienced together was so ridiculous that humor often emerged organically, with little effort.

However, crafting the book’s tone was a delicate balance, as the story is multi-layered. It developed over numerous rewrites, and achieving consistency wasn’t always easy. The biggest creative challenge for me was ensuring I hit all the emotional notes without the story dragging.

I wanted this book to be a page-turner, and all the elements I needed to accomplish that were present: plenty of drama, lots of conflict, and it all hinged on how I presented them.

There were many sides to Holly. She was endearing, warm, compassionate, and hilarious. But she was also afflicted, and I had many challenging experiences with her. But my sole intent in writing this book wasn’t to bash her. It was to honor her, celebrate our friendship, and take readers on a wild ride that would have a profound impact.

FG: What’s the most unexpected thing you’ve learned about yourself through the process of writing this book?

JC: The most surprising thing I learned was that I could write another book and get it published. When I began working on this story ten years ago, I didn’t envision it as a book. I thought it might make an interesting article or perhaps a short story. The idea of writing a whole book felt intimidating to me. The voice I had created for A Low Life in High Heels was the only one I knew, and that voice wouldn’t work for Love You Madly. I needed to develop my own voice, which initially proved challenging because Holly’s voice kept emerging. I constantly had to push her away and say, “Back off, bitch!” However, over time, I did manage to develop a voice, and I believe it works well for the story.

FG: What was the most rewarding part of writing about someone as iconic and multifaceted as Holly Woodlawn?

JC: The most rewarding aspect for me was reliving all the fantastic and outrageous times we shared. I also love that, through this book, young people will have the opportunity to discover Holly. Thirty years ago, when A Low Life in High Heels became a success and reignited Holly’s fame, people minimized and overlooked my contributions to the story. Whenever Holly spoke about our collaboration, she essentially said that she spoke while I typed. This downplayed everything I did to make that book possible. Therefore, writing this new book on my own and receiving such a positive response has not only been rewarding but also incredibly validating.

FG: How did your experience writing A Low Life in High Heels influence your approach to Love You Madly, Holly Woodlawn? Did any lessons or insights from that journey shape the creation of this book?

JC: I was honestly disappointed with the numerous typos I noticed after the publication of A Low Life in High Heels. I wrote it so quickly that I didn’t have time to polish it thoroughly. In contrast, Love You Madly, Holly Woodlawn took ten years to complete, and because it hadn’t been pre-sold, I had the luxury of taking my time. I worked diligently to create a clean, succinct narrative that really packs a punch.

I wanted to fulfill the wishes Holly left unfulfilled in the previous book with this new one. For example, while we were working on Low Life, Holly dreamed of a wild, fun, and vibrant cover, but she never received that. With Love You Madly, I created a cover that she would love. We faced many challenges with A Low Life, and Love You Madly, Holly Woodlawn was my opportunity to correct those issues and make things right.

Holly Woodlawn / Copyright ©️Peter Palladino

FG: What insights or emotions do you hope readers will take away about Holly after reading your book?

JC: I want people to love Holly the way I did when we were together, living at the Las Palmas Apartments and working on Low Life. I want them to laugh out loud and savor all the wacky adventures we experienced. Most importantly, I want people to understand that the essence of the human spirit is what truly matters. That is what defines a person, not their sexual organs. When Holly and I were collaborating, people frequently asked me if she “cut it off” or what bathroom she used. Who cares? Yet, people were completely preoccupied with her genitalia.

So, when I write about that in Love You Madly, I do it in an over-the-top way. This was intentional, almost like a covert “fuck you” to everyone who was rude enough to ask those stupid questions.

I want people to understand the difficult choice Holly faced when she dropped out of school and left home at 15. Her story highlights a harsh reality: if the government genuinely prioritized diversity, equity, and inclusion, perhaps children who feel different wouldn’t be so overlooked or unsupported.

This reminds me of Anita Bryant’s infamous “Save Our Children” campaign in 1977. I was 14 when I saw Anita get a pie in the face on the evening news. I vividly remember my grandmother watching alongside me, saying, “They should leave her alone.” Hearing those words from someone I loved deeply, knowing they reflected a rejection of who I truly was, was devastating. That kind of rejection leaves lasting scars on a child.

If Holly had grown up in a society that celebrated diversity and fostered inclusivity, her path might have been very different. Instead, she faced challenges that no child should ever have to endure.

FG: If Holly were here today, how do you think she would respond to your portrayal of her in the book?

JC: She would be thrilled because the portraits of her are gorgeous. It’s such a fun story, and she is an absolute delight. We had our ups and downs, but even when she was having a hissy fit — screaming about Madonna or cursing me out — she was hilarious.

FG: What was the most challenging part about sharing your own story alongside Holly’s? Did you ever feel exposed by revealing so much of yourself?

JC: I felt it was essential to reveal certain things about myself because I thought it was important for readers to understand why I got involved with Holly in the first place. We were two desperate, broken misfits struggling to make our dreams come true because, quite frankly, that’s all we had to look forward to.

Writing this story never made me feel exposed, but it did leave me emotionally drained. The most difficult part was revisiting the devastating situation with Madonna and the subsequent chaos that followed. These events were tough to confront because I had buried those painful emotions for over thirty years, never truly processing them. My anger over their occurrence kept me from facing them head-on. Reliving those moments while writing was deeply challenging — it made me cringe, brought tears to my eyes, and reopened wounds I had tried to ignore. What we endured was both unnecessary and heartbreaking, and it should never have happened. Despite countless revisions, I could never dull the pain of that section. It was, and always will be, gut-wrenching to relive.

Holly Woodlawn / Photo by Thomas Cunningham

For fans of Hollywood history, LGBTQ+ culture, or anyone who appreciates a story of perseverance and love, this book is a must-read. Holly’s story is one of triumph and tragedy, humor and heartbreak, and Copeland’s heartfelt prose ensures her legacy will continue to inspire for generations to come.

Don’t miss your chance to take a walk on the wild side — grab your copy of Love You Madly, Holly Woodlawn, and experience the magic of this unforgettable memoir.

Love You Madly, Holly Woodlawn book link: https://a.co/d/iCl0MBl

Frank Gaimari is an author and film reviewer in Seattle, where he lives with his husband and their two golden retrievers. You can learn more about his work at http://www.FrankGaimari.com.