By Valerie Milano
Palm Springs, CA (The Hollywood Times) 10/29/25 – Few performers embody the intersection of comedy, activism, and authenticity quite like Jason Stuart. The veteran comedian, actor, and filmmaker joined me, his longtime friend, for a lively and heartfelt conversation ahead of his performance at the Sunset Music and Comedy Festival, where The Hollywood Times proudly serves as media partner.
Our chat, equal parts banter and reflection, unfolded with Jason in his Palm Springs home, his mother, as always, making a brief cameo from downstairs. “Mom, stop calling me, I’m doing an interview with Valerie!” he laughed. That kind of familial humor is exactly what makes Jason’s comedy so irresistibly human.
Performing in Palm Springs feels like a homecoming for Jason. “It’s show business, it’s like a small, big town,” he said. “I love it here. People always ask why I left L.A., and I tell them, I was looking for a parking spot and just kept driving!”
He’ll bring that charm to Two Roads: From Roots to Broadway on Friday, November 7, at the Palm Springs Cultural Center, alongside powerhouse performers Ann Hampton Callaway and Amythyst Kiah. The show celebrates storytelling through both music and laughter, a natural fit for Jason’s wide-ranging career.
When asked what the evening’s theme means to him, Jason reflected on his journey. “I’ve always dreamed of Broadway,” he said, recalling performances at New York’s Town Hall with legends Sandra Bernhardt and Joan Rivers. “So, I’ve kind of been Broadway-adjacent,” he quipped.
Jason’s path from stand-up clubs to film and television has been guided by an unwavering belief in authenticity. “Coming out changed everything,” he explained. “I stopped performing in disguise and started being myself. Ironically, one reporter said I became more masculine after coming out, which just meant I finally felt comfortable in my own skin.”
Comedy, for Jason, is no longer about defense. “It used to be armor,” he said. “Now it’s just fun.” His latest venture, a crowd work special, takes that joy even deeper, inviting audiences into the act. “I’ve been doing crowd work for years before it became trendy,” he laughed. “Now I’m jumping on my own bandwagon.”
But Jason’s storytelling extends far beyond the mic. His new film, Redlining, which he directed, tackles issues of gerrymandering and generational wealth through the lens of two families, one Black, one white, grappling over shared property and legacy. “It’s about fairness,” Jason emphasized. “About who gets to build generational wealth, and who’s been denied it.”
A pioneer in queer representation long before “diversity and inclusion” were buzzwords, Jason spoke candidly about Hollywood’s ongoing evolution. “We’re all catching up,” he said. “For those of us who didn’t get the same opportunities as straight actors early on, it’s about competing on the same level now. But I’m grateful, I get to tell stories that matter.”
His advice for emerging artists? “Be yourself. Don’t chase roles that just mirror who you are, create new ones. That’s what acting’s for.”
Jason’s memoir, Shut Up, I’m Talking, offers readers both laughter and lessons. “The only difference between me and anyone else,” he said, “is that more people know me. My father used to tell me to ‘wear a tie to show you mean business.’ What he really meant was: show up as your best self. That’s what I try to do every time.”
As Two Roads from Roots to Broadway nears, Jason sees comedy and music as two sides of the same coin. “Whether it’s a song or a joke,” he said, “if it makes you feel something, laugh, cry, dance, it’s all about connection.”
And when audiences leave the theater? Jason hopes they’ll remember “that I’m single and looking for someone great,” he joked. “Preferably someone younger, so they can push my chair!”
The laughter may come easy, but the impact of Jason Stuart’s voice, humorous, heartfelt, and profoundly human, lingers long after the curtain falls.
Catch Jason at Two Roads from Roots to Broadway on Friday, November 7, at the Palm Springs Cultural Center, as part of the Sunset Music and Comedy Festival.
Follow The Hollywood Times for exclusive interviews, red carpet highlights, and festival coverage on TheHollywoodTimes.today and AspiringMagazine.com.
Editor’s Note:
Jason Stuart is not only one of Hollywood’s most versatile talents but also a cherished personal friend whose candor and courage continue to inspire. – Valerie Milano
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