The Trouble With Billy: How a ’90s Star Lost It All—and Filmed the Comeback

by | May 27, 2026

Being around celebrities was a normal occurrence for Billy McNamara growing up—less a novelty than a kind of ambient reality. Thanks to his mother, his childhood unfolded in rooms filled with artists, actors, and directors. “These people were really amazing people… real artists,” he recalls. Floating through that orbit were names that defined an era—Ryan O’Neal, William Goldman, Elliott Gould, Bob Fosse, George Roy Hill—figures McNamara absorbed as “a fly on the wall, just an observer.”  

It left an imprint. “That’s it.  I want to do that.” McNamara pinpoints the moment, as a child, when he knew he wanted to be an actor.  

His mother, a Manhattan-based interior designer, however, had other plans. The glamour came with a warning label. She “really tried to snuff out that flame,” steering him instead toward something safer, more stable. Boarding school on the East Coast. The Upper East Side. Columbia University. A future in finance. “I was kind of thinking about being an investment banker,” he says, “because that’s what everybody did.”  

But the pull toward acting didn’t fade—it just went underground.    

In New York, McNamara began quietly building a second life. He attended only the minimum number of college classes while seeking out small, serious acting studios. “I found all these independent, really good acting schools,” he says. He remembers sitting in one of them, as a total beginner, beside another total beginner, named Ben Stiller. “We were like two… absolute new students.”  

He trained at the Lee Strasberg Theatre and Film Institute. Then came Williamstown Theatre Festival—his version of artistic boot camp. “Seven days a week… eight in the morning till midnight,” he says. “Not even Sundays off.” It was grueling, exhilarating, and formative. “We just loved it so much.”  

The ascent, once it began, was swift. “Within six months of starting this, I was making money in commercials… a lot of money,” he says. “And within a year, I was doing movies… working nonstop.”  

Real life, for McNamara, would often become the blueprint for his work. But it would also become something else: the story itself.  

Ask him about 1989’s fantasy comedy Dream a Little Dream, starring Corey Feldman and Corey Haim, and he doesn’t wax nostalgic. He sounds puzzled.  

“It’s very strange,” he says. “It was not something I ever thought about… I didn’t think it was any good.”  

He pauses, still slightly incredulous at its enduring reputation.  

“But, people still contact me about it to this day.”  

It’s a humble, almost bemused distance from a film that audiences have embraced in ways he never anticipated—proof that, as he puts it, once something is released, “how the world receives it… That’s up to the universe.”  

If Dream a Little Dream is the enigma, Stealing Home is the cornerstone.  

“That was my big, big break,” McNamara says. “That movie really put me on the map.”  

Cast as the younger version of Mark Harmon’s character, he found himself in the kind of career-defining moment that actors spend years chasing. The competition was fierce. “Very famous actors tested for the role,” he says. “Four or five guys at the end.”  

Then came the moment that still feels surreal.  

“We’re testing with Jodie Foster herself,” he recalls. “And at the end of the screen test… she pointed at me. She goes, ‘That’s your guy.’”  

Within 24 hours, the role was his.  

For McNamara, it wasn’t just a job—it was something closer to destiny. As a child, he had watched Foster in Taxi Driver and Alice Doesn’t Live Here Anymore—memorizing performances, studying her instinctively. “I was just mesmerized,” he says.  

Now, suddenly, he was her co-star.  

What followed wasn’t what he expected.  

Foster kept her distance on set—no idle chatter, no shared lunches, no off-camera bonding. “She didn’t socialize,” he says. “She would go back to her trailer and isolate.”  

At first, he didn’t understand. Then came the turning point. Finally, after two and a half months of “the silent treatment” on set, towards the end of the shoot, Foster, uncharacteristically, called out McNamara’s name and asked him to help her do the shopping for the wrap party.  

McNamara was shocked, as she almost never spoke to him unless they were working a scene.  

And then, in a moment that feels lifted straight from a screenplay, reality blurred again. After the wrap party, Foster tapped McNamara to take a late-night walk on the beach. “It was like a scene out of the movie,” he recalls. “We held hands and walked in silence. Then, Jodie broke the silence with, “’Hey, I really like you, Billy, and I think you’re a great actor.’”  

McNamara was shocked. He wanted to know why, if she liked him so much, she didn’t talk to him.  

“‘How did you feel when you came to set?’ Jodie asked me.”  

McNamara answered that he couldn’t wait to interact with her. It was his only opportunity to connect to her, and the memorized lines were insignificant.   

“‘Exactly, it’s got nothing to do with the lines,’ she replied.”  

In that moment, everything clicked. McNamara realized that it was Foster pulling the strings, which elevated his acting to levels he himself was not capable of.  

“I’m not a great actor. She made me great,” McNamara says now.  

To him, Foster wasn’t just guiding a performance—she was shaping it in real time, intuitively, almost invisibly. “She’s a guru… she’s like a sorcerer,” he says. “She’s like one of these avatars that walks the earth.”  

After Foster had praised his acting, McNamara, still fishing for compliments, asked whether that was the reason he was cast. He calls Foster’s quick response.   

“‘No. The other guys were too tall.’”  

McNamara laughs.  

Once again, real life mirrored cinema—fleeting, heightened, and impossible to hold onto.  

But Hollywood arcs rarely stay linear.  

What followed was a career spanning 165 film and television credits. He starred alongside Jeff Bridges in Texasville, Sigourney Weaver and Holly Hunter in Copycat, which recently trended on Netflix, and Tom Berenger in Chasers. On television, he portrayed Montgomery Clift in Liz: The Elizabeth Taylor Story, earned a CableACE Award nomination for Wildflower, and held a series lead on the CW’s Disaster Strike Force.

“I had an ongoing drug problem, and that really gets in the way,” McNamara says plainly. Today, he marks “21 years sober… no drugs, no alcohol,” calling it his greatest success. Sobriety reordered his values. 

Then came a shift few could have predicted: animal rights activism.  

He made a deliberate decision to leave Hollywood for animal activism, joining Sea Shepherd Conservation Society, traveling to Taiji, Japan, where he was arrested documenting the annual dolphin slaughter. The footage his team captured contributed directly to The Cove, the Academy Award-winning documentary. He threw himself into it completely. “It becomes the only thing in the world to you.”  

Back in the U.S., he developed alongside Alison Eastwood, going undercover to document exotic animals in illegal captivity, work that would eventually sell: Animal Intervention for National Geographic. But the work came at a cost. “You don’t get paid,” he says. “You end up going through your savings.”  

He assumed he could return to acting at any time.  

“But as you get older… not so.” By the time he returned to Los Angeles, his savings were gone. 

That tension—between who he was and where he ended up—became the foundation for The Trouble With Billy, a project over a decade in the making.   

“So, what happened…” he begins, launching into the origin story: years spent filming undercover in Texas, living off dwindling funds, piecing together footage while his own life unraveled.  

The result is a series that blurs fiction and autobiography, peeling back the layers of fame.  

At its core is a relationship with a pit bull named Boo.  

Billy McNamara reflects on Hollywood, sobriety, animal activism, and the extraordinary true story behind The Trouble With Billy.

Landlords turned him away and told him he could stay if he gave up the dog. Within 24 hours, they were back in the car. When Boo was diagnosed with cancer, her chemotherapy cost $1,200 a week. McNamara traded his Honda Civic for a 1998 Chevy Monte Carlo, one that could idle for hours with the air conditioning running. He spent everything keeping her alive. During this period, he reached a point of such profound despair that he stood at the edge of suicide. “I stayed alive for her. That was my reason for being.” 

And the stranger elements? The UFO encounters woven into the narrative?  

“Unfortunately, it’s based on a lot of facts,” he says. “The UFO stuff—that’s all true too.”  

The making of The Trouble With Billy is as improbable as the story it tells.  

McNamara funded the early episodes himself on a microscopic budget. “I wrote it, I directed it… I did everything,” McNamara says. “Props, wardrobe, hair, makeup… everything.”  

At one point, he was instructing camera operators he’d found online: “Just stand here and hold the camera… change the lens.”  

When the money ran out, he considered stopping. Friends urged him to cut it into a film and move on.  

Then, good friend and actor Randall Batinkoff and his wife, Hilary Lambert, showed the film to Randall’s sister, Stephanie Winston Wolkoff, and her husband, David Wolkoff, who helped expand it into a full series through their production and distribution company, ZTA Entertainment, LLC. 

And yet, somehow, it worked.  

If there’s any lingering expectation about how The Trouble With Billy will land, McNamara doesn’t cling to it.   

“Or not,” he shrugs when asked if it will find an audience. “At least I did it.”  

In the end, the series distills his life into a single, disarming line:  

“It’s based on a true story… unfortunately.” And he wouldn’t tell it any other way.  “It was very cathartic taking some of the worst episodes in my life, some of my biggest mistakes, and distilling them into playable scenes. People can’t believe it really happened, but as we say in the show, unfortunately, most of it did.” 

It’s a joke—but not really.   

Because Billy McNamara’s story isn’t a clean narrative of success or failure, it’s something stranger, more uneven, more real. A life where childhood dreams come true, slip away, and then reassemble themselves in unexpected ways.  

“It’s a double-edged sword,” he says.  

The 10-episode series boasts an unbelievable cast that includes Randall Batinkoff, Billy Baldwin, Angus Macfadyen, Alison Eastwood, Claudia Charriez, Costas Mandylor, Ele Keats, Lindsey Pelas, Marilu Henner, Robert Wagner, and the late actors Corey Parker, Sally Kirkland, and Tom Sizemore. They all worked for almost nothing because they believed in the story. In one of its most significant creative choices, McNamara cast transgender actress Claudia Charriez as a central love interest, portrayed with full authenticity and emotional weight. A portion of the project remains deeply personal: “20 percent” of proceeds go to animal rescue efforts connected to Alison Eastwood, with plans to expand support to other organizations, including LGBTQ organizations. 

Billy McNamara reflects on Hollywood, sobriety, animal activism, and the extraordinary true story behind The Trouble With Billy.

The Trouble with Billy is now streaming on Red Coral Universe, bringing his signature wit, perspective, and life experience to a new generation of viewers.

To watch the complete first season, visit TheTroubleWithBilly.com.

 

Photographer: Eden Dozier

Post-production: Lidiia Berezhna
Layout: Jennie Salmorin
Publisher: Derek Warburton

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