Holly came from Miami, F-L-A
Hitch-hiked her way across the USA
Plucked her eyebrows along the way
Shaved her legs and then he was a she
She says, “Hey babe, take a walk on the wild side”
—“Walk on the Wild Side,” Lou Reed, 1972
Holly Woodlawn, the transgender actress—one of Andy Warhol’s original “superstars”—made her mark in cult cinema with her affecting turn in Paul Morrissey’s Trash (1970), but it was Lou Reed’s opening lyrics to “Walk on the Wild Side” that cemented her place in pop culture history, as a footnote to some, but a trailblazer to others.
Either way, by the ‘80s, Woodlawn was a down-and-out survivor in Los Angeles, hanging on by her acrylic nails with sporadic cabaret gigs, phone-sex lines, gallons of Glen Ellen Chardonnay —and by turning the occasional trick.
Enter Jeff Copeland, a gay small-town Missouri transplant with stars in his eyes and dreams of making it as a screenwriter. Together, they wrote her 1991 autobiography A Low Life in High Heels: The Holly Woodlawn Story (St. Martin’s Press), filling details Reed left out.
Woodlawn died in 2015, but Copeland’s new memoir, Love You Madly, Holly Woodlawn (Feral House, 2025) revisits their unconventional partnership. It is a rambunctious ride through the grit and glamour of ‘80s Los Angeles, with everyone from Madonna to Pee-wee Herman lurking around the edges of the page. Imagine Sunset Boulevard written with a sharpened eyebrow pencil.
Windy City Times spoke to Copeland, now residing outside St. Louis, about the book and memories of Holly.
Windy City Times: Why do you think Holly Woodlawn’s life still resonates today?
Jeff Copeland: She was a trailblazer. I think Holly Woodlawn’s story is a testament to why DEI initiatives are so important.
WCT: Why do you say that?
JC: Because Holly ran away from home in 1962. I grew up in the 1970s. During both those periods, bullying was accepted. We lived in a homophobic culture. If a gay person appeared on television, it was usually in a sitcom, and they were the butt of the joke. That’s why DEI matters. When you grow up being told you’re worthless, a pervert—it’s damaging. That’s why Holly ran away. She couldn’t conform to what her parents wanted. She had the guts to hit the road, go to New York, and live on the streets.
WCT: Growing up gay in a small town outside St. Louis—what did the Warhol scene represent to you?
JC: I wasn’t into the New York underground. I had no knowledge of Warhol or the Factory. I grew up in a redneck, homophobic community where I didn’t fit in. My escape was old movies—Joan Crawford, Barbara Stanwyck, Bette Davis. I read all their biographies—and Rona Barrett’s autobiography. That’s why I decided: “Go to Hollywood. The Midwest isn’t for you.” I wanted mainstream success, Rona Barrett–style.
WCT: How did you first meet Holly?
JC: I was at a birthday party and saw this person across the room. I didn’t know if it was a man or a woman, so asked, “Who is that?” Someone said, “Oh, that’s Holly Woodlawn. Don’t bother; she’s a mess.” But she stuck in my head. I thought: You need to do something bold to relaunch your career. Write your own movie. Cast someone interesting who’ll get you press. That’s how Holly and I came together.
WCT: What made you want to revisit that story now?
JC: I wrote Love You Madly, Holly Woodlawn because I didn’t want to forget all that Holly meant to me, and all the ups-and-downs that we shared. Whenever Holly talked about how A Low Life in High Heels came to be in the press, she never told the whole story. It was usually one line: “Jeffrey called me up and said I should write a book.” What really happened is that our movie project was discovered in the trash by a literary agent’s assistant. That’s what jumpstarted our crazy adventure, which just got more ridiculous over time.”
WCT: Your book also captures ‘80s gay Hollywood as both glamorous and gritty.
JC: Yeah. AIDS was raging then, so it was terrifying, but also a very fun time.
WCT: And our language around gender identity for someone like Holly has dramatically changed, too.
JC: There’s much more sensitivity now. Back then, no one said they/them. On Saturday Night Live, the “Pat” character was a joke. No one had language for gender fluidity.
WCT: Holly was still referred to as an Andy Warhol “superstar.” Ironic, since by the time you meet her, she was struggling and at times turning to sex work to pay her rent.
JC: Exactly. Warhol used his superstars. They were the antithesis of movie stars. It was all bullshit and ephemeral. Holly used me the same way. When someone better came along, I got ditched. It was hard for her to ditch me because of our legal ties, but yeah, that’s what happened.
WCT: Yes, because you write trying to turn the book into a screenplay ultimately strained your friendship with her.
JC: It destroyed it. She was my best friend. But writing Love You Madly was about taking a terrible wrong and making it right, taking that horrible turd and spinning it into gold.
WCT: Did the screenplay of Low Life in High Heels ever get made?
JC: No. We wound up in development hell. To Wong Foo and Priscilla Queen of the Desert came out and stole our thunder—no one wanted another drag-queen movie. Holly’s lawyer was supposed to represent both of us, but once conflicts started, things got messy.
WCT: My favorite aspect of the book is the vivid portrait of a young writer in Hollywood.
JC: I moved to Los Angeles in 1985 for TV and film, but didn’t catch a break until I turned 30. It was a crazy, precarious journey filled with hardship and struggle, with Holly in the middle.
WCT: At one point, you even took a photography assistant gig that had you powdering a model’s butthole—not exactly the Hollywood break you were hoping for.
JC: [Laughs] That was demoralizing. I was a prude, honestly. When I took that photography job, I honestly didn’t think it would involve porn. I thought they were just male nudes for greeting cards. Porn, drugs—not for me. I wanted to win an Oscar, not an AVN Award.
WCT: Would you consider adapting Love You Madly for the screen?
JC: Maybe as a stage play—even a musical. I’ve thought about who could play Holly Woodlawn, and I’d love to see Jane Lynch. If you look at photos, they don’t look identical, but Jane has that blend of masculine and feminine that would work beautifully.
WCT: What do you think Holly would make of this book?
JC:
I think Holly would be genuinely thrilled with Love You Madly, Holly Woodlawn, because the story is so fun and funny, and for the most part she is just delightful in it. One of her closest friends told me this book captures the real Holly Woodlawn. Even though this story does have moments when it’s unflattering, those moments give rare insight into the real human Holly was.
This article has been edited and condensed for length and clarity.
Chris LaMorte is a Chicago-based journalist and writer whose work has appeared in Windy City Times, Chicago Tribune, Crain’s Chicago Business and at ChrisLaMorte.com.