Dolly Parton paid for her longtime driver's gender-affirming care
Published in Entertainment News
If people need another reason to understand why Dolly Parton was so beloved in American culture, the entertainer, who died Aug. 25 at age 80, was known for being genuinely kind and generous to the people who worked for her.
That includes her longtime driver and assistant, Jason Pirro, with news surfacing this week that the country star, philanthropist and LGBTQ+ icon paid for his gender-affirming care in the 1990s, LGBTQ Nation reported.
Pirro was a well-known figure in Parton’s entourage — the heavyset chauffeur in a tuxedo who also became her “good friend,” trusted adviser and favorite wardrobe consultant, LGBTQ Nation reported. Over the 40 or so years that Pirro worked for Parton, he expressed appreciation for his boss’ support, including when a tabloid outed him as transgender man in a 1990 cover story.
As revealed by the editor of Parton’s 1994 autobiography, the Grammy winner’s support of Pirro extended to paying for his gender-affirming care.
“She was rightly known for her humanity and decency, and when a member of her team was transitioning — this was in the ’90s — she paid for their care,” Elissa Altman, Parton’s editor at HarperCollins, wrote on Instagram following news of Parton’s death.
“She was a profoundly good and kind person; it wasn’t an act,” Altman said.
Pirro said as much about his boss back when Star magazine approached him about a planned cover story, which tried to sensationalize his transgender journey and his relationship with Parton. He told Star, “I’m not real comfortable talking about myself. Dolly knows all about me and is a very nice lady.”
The Star story may or may not be the source of a memorable line from the singer, affirming her allyship with the LGBTQ+ community, LGBTQ Nation reported.
“If I were a man, I’d be a drag queen,” the Star story quoted Parton as saying. “I enjoy being a trashy dresser and I love gaudy things. I love to play with hair and makeup.”
For the most part, Pirro and Parton kept their friendship out of the spotlight, but his name surfaced a few times, according to LGBTQ Nation. Parton thanked him in the liner notes for her 2016 album “Pure & Simple” for his “time, love, and attention to details.” He also contributed to her 2023 fashion memoir, “Behind the Seams: My Life in Rhinestones.” In a Sept. 1 Facebook post, Gay Star News praised Parton for standing by Pirro, saying, “No headlines, no press tour — just three decades of loyalty. That was Dolly.”
The year Parton published “My Life in Rhinestones,” she also voiced support for the transgender community, shortly after her home state of Tennessee passed a bill that allowed for discrimination against trans people. In an interview The Hollywood Reporter, she said about the bill: “Well, what I always say, ‘I just want everybody to be treated good.'”
“I try not to get into the politics of everything. I try to get into the human element of it,” she continued. “I have some of everybody in my own immediate family and in my circle of employees. I’ve got transgender people. I’ve got gays. I’ve got lesbians. I’ve got drunks. I’ve got drug addicts — all within my own family. I know and love them all, and I do not judge.”
“If there’s something to be judged, that is God’s business,” she also said. “But we are all God’s children and how we are is who we are.”
©2026 MediaNews Group, Inc. Visit at mercurynews.com. Distributed by Tribune Content Agency, LLC.












Comments