Highlights
- Dolly Parton’s chauffeur and later assistant of 30+ years, Jason Pirro, is a transgender man she long supported.
- Pirro told Star in 1990 that Parton knew about his transition and treated him with warmth and respect.
- Parton publicly thanked Pirro by name in her memoir, a 2016 album, and her 2023 book, over three decades.
Dolly Parton died Tuesday (August 26, 2026) in Nashville at 80, after a brief battle with cancer.
In the hours since, tributes have poured in from across American life.
Her nephew, Bryan Seaver, delivered the news himself, on video. “She never saw a door she couldn’t open,” he said.
Among the memories being shared this week is a quieter one. It involves a man named Jason Pirro, who spent more than three decades as Parton’s Hollywood chauffeur and later as her personal assistant.
Pirro is a transgender man. Parton knew that from the start.
The public first learned of the arrangement in 1990, when the tabloid Star ran a story on Pirro built around his gender history. A transgender newsletter called Twenty Minutes picked up the interview that same year, preserving Pirro’s own words for the record.
“Dolly knows all about me and is a very nice lady,” Pirro told Star at the time.
He was 44 that year, working steadily, driving Parton to meetings and film sets whenever she came through Los Angeles. Those who knew him described him, in that same article, as gentle and easy to like.
The relationship outlasted the tabloid cycle by decades.
In her 1994 memoir, Dolly: My Life and Other Unfinished Business, Parton thanked Pirro by name in her acknowledgments. She also brought him up, unprompted, while answering a reader question about sex-change operations.
“If I hadn’t been a woman, I would have been a drag queen,” she said, before crediting Pirro directly as the friend who’d taught her what she knew on the subject.
Pirro’s name surfaces again in the liner notes of Parton’s 2016 album, Pure & Simple, where she thanked him for his “time, love, and attention to details.” He’s credited once more in her 2023 book, Behind the Seams.
That’s three decades of employment, acknowledged by name in the front matter of at least three separate projects. It isn’t a footnote. It’s a pattern.
Parton’s support for trans people was never confined to her payroll, either.
When North Carolina passed its bathroom bill in 2016, she didn’t dodge the question. “I just know if I have to pee, I’m gonna pee,” she said.
Asked again in 2023, as her home state of Tennessee moved against trans residents, her answer stayed just as plain. “I know and love them all, and I do not judge,” she told The Hollywood Reporter, describing the transgender people, gay people, and others already in her own family and on her staff.
None of this required Pirro to become a spokesperson. He does not appear to have given an interview about Parton in the thirty-plus years since that one tabloid story, and outlets reaching out to him this week say they have not yet heard back.
That, too, might be the point. Parton gave him a job, a friendship, and, as far as the record shows, no pressure to explain himself on camera.
She spent her career being loud about rhinestones and quiet about the people she loved. Pirro was one of them, for a very long time.
