Author Jeff Copeland was not like the other boys growing up in exurban St. Louis in the 1970s. Rather than playing sports, he was fascinated by the glitz and glamour of Hollywood. Copeland decided early on that he wanted to write about celebrities, and with the help and encouragement of his resourceful mother, who came up with inventive ways to get their attention, he was able to land big-time celebrity interviews when entertainers visited the area. While still in high school, he successfully published pieces in St. Louis daily newspapers.
Cover photo by and used courtesy of Peter Palladino
Immediately after graduating from Webster University in 1985, he borrowed a little money from his working-class parents and crossed the country, bound for Los Angeles in an old, overheating Plymouth — without a job or the faintest idea of how to secure an apartment — fueled entirely by his ambition to become a television writer.
In the 1980s, one could say that Los Angeles was between its glamorous eras. The entertainment industry was churning out a lot of cheap crap, and the city was gritty and tacky by today’s standards.
After landing a few entry-level positions by channeling his mother’s resourcefulness, Copeland was barely eking out a living. But he got a big bump forward when he landed a production assistant job at Paramount Pictures on a landmark gay-themed TV series called Brothers.
“A gay show written and produced by straight white men,” he says with rolling eyes. “Go figure. But I was so thrilled to be there. I remember thinking I’d hit the jackpot when I got that job.”
In short order, however, the 1988 Writers Guild strike put the kibosh on that project. Most TV production shut down and Copeland was quickly laid off. To survive, he worked a low paying secretarial job at an A-list PR firm that represented Michael Jackson and Barbra Streisand.
“It was the worst job ever,” he says. “My first day, there was so much pressure and stress, I chugged a Budweiser for lunch just to calm down.”
But he never lost hope that one day things would ultimately work out.
Jeff Copeland, Marie Connolly and Hollow Woodlawn. Facebook.
About seven months later, while at a party, he spotted transgender actress Holly Woodlawn, who skyrocketed to fame in the 1970s as one of Andy Warhol’s most beloved superstars. When Lou Reed sang about her in his classic radio hit,
“Walk on the Wild Side,” Woodlawn was forever immortalized in the annals of pop culture. Still, unlike the earlier superstars of the Warhol Factory (i.e. Edie Sedgwick), she was no blue-blooded heiress: She was a petty thief, an ex-con, and a street urchin who hustled tricks to survive, which made her trajectory from the gutter to the screen all the more extraordinary.
Woodlawn’s life had been a rollercoaster ride through New York’s underground arts world. Throughout the ’60s and ’70s, she was a fixture in New York’s avant-garde theater scene, appearing in a handful of movies (most notably Andy Warhol’s Trash), partying at Studio 54, and headlining a successful cabaret act.
By the 1980s, though, the creative world had changed dramatically, and with it Woodlawn’s whole life. The New York arts scene was ravaged by AIDS; far too many of her friends had died, and the theaters and cabarets where she performed had gone dark. Lost and reeling, she decided in 1988 to swap coasts and try life in Hollywood in the hopes of rekindling her limelight. But opportunities in the land of her namesake were slim, and the prematurely faded superstar wound up living in a squalid apartment on the verge of eviction.
Holly Woodlawn. Courtesy of Jeff Copeland.
Then, at that fateful party in 1988, young Jeff Copeland caught his first in-person glimpse of Holly Woodlawn. He was immediately fascinated by the aging star’s strange presence, which was only heightened by the fact that she was out of drag. Their eventual meeting a few days later led to a life-changing collaboration, in which Copeland eventually
became Woodlawn’s biographer, promoter, handler, coach, dear friend and biggest fan.
Copeland’s initial dream was for Woodlawn to star in a movie he’d written and was trying to produce.
“That movie never got made because I didn’t know what I was doing,” he admits. “I was just pushing to make something good happen for us.”
Holly Woodlawn. Photo credit: Greg Gorman.
Ironically, however, something good did happen when his screenplay was literally pulled out of the trash by a literary agent’s assistant. “The assistant called me up and said, ‘We don’t work with screenwriters. We represent book authors. And I think there’s a book in Holly Woodlawn.”
So Copeland teamed up with Woodlawn to write her autobiography, A Low Life in High Heels: The Holly Woodlawn Story. It was an arduous task fraught with challenges. Naysayers declared that she was a mess and that he was wasting his time. But he’d grown genuinely fond of Woodlawn, and together they persevered.
A Low Life in High Heels was published by St. Martin’s Press in 1991. It didn’t make the bestseller list — but when Madonna attached herself to the film rights, Woodlawn’s fame reignited in a most spectacular way and Copeland was able to get a taste of Hollywood success. The two of them were glitzing it up, flying between New York and LA for events and partying with the stars. Woodlawn did a cabaret events around the country, and even appeared in Madonna’s star-drenched ultra-clubbing video for “Deeper and Deeper.”
As is its cruel way, the spotlight didn’t linger on Woodlawn much longer, and Copeland meanwhile found other film and TV-related projects to keep him occupied, eventually becoming an Emmy-nominated television producer. He has wound his own path through the industry, but he credits Woodlawn for giving him his first big break.
“One night, while thinking about all the shows I’d worked on, I realized none of them compared to the fantastic whirlwind I experienced with Holly,” he says. “It was quite magical. And because I didn’t want to forget those memories, I began writing them down.”
That was in 2016, a year after Woodlawn’s death. But then other projects got in the way and the story was shelved until 2019, when Copeland moved back to St. Louis to help with his parents’ care.
“Like Holly in 1988, I was lost,” he says. “My career was over. And it was time to reinvent. And my memories of Holly Woodlawn, and my intent to honor her and celebrate the journey we shared, allowed me to do just that.”
To Copeland, Woodlawn is more than just a footnote in LGBTQ+ history. “Holly’s story is more relevant than ever because she’s a great example of why diversity, equity, and inclusion programs are so important,” he said in a recent interview. “As a kid, she was shamed and mistreated because she was different, so she ran away from home and survived as a teenage prostitute. Had she grown up in a supportive, encouraging environment, she would have had other options.”
Love You Madly, Holly Woodlawn is a madcap, yet poignant adventure — a tale of two unlikely friends who dramatically changed the course of one another’s lives. If you think it might be too racy for you, consider taking a walk on the wild side.
