Dolly Parton supported trans man who worked with her for more than 30 years

As LGBTQ+ fans remember Dolly Parton following her passing, a piece of her history with the trans community is resurfacing. For decades, Parton employed and remained close to a transgender man named Jason Pirro.

Pirro was working as Parton’s chauffeur by 1990, when a story about him appeared in Star, a tabloid paper, and was subsequently reprinted in transgender newsletters of the era. An old eBay listing of the magazine, as reported by Them, shows outdated language about trans people in the headline, but Pirro’s own comments made clear that Parton knew about his transition and treated him with kindness and respect.

“Dolly has been good to me,” Pirro told Star at the time. “Dolly knows all about me and is a very nice lady. Whenever Dolly comes into Hollywood for a meeting, or for business, or for filming, or just staying here, she calls me and I drive her around.”

An August 1990 issue of the transgender newsletter Twenty Minutes reported that Pirro was chauffeuring Parton around Hollywood, while another contemporary newsletter from trans author and activist Lou Sullivan also highlighted his work with Parton and other celebrities.

Parton later mentioned Pirro by name several times in her 1994 memoir, Dolly: My Life and Other Unfinished Business. In a Q&A section addressing her views on trans people and gender-affirming surgery, Parton was asked what she thought about “sex-change operations”.

‘I just want everybody to be treated good’

“Well, I’ve always said that if I hadn’t been a woman, I would have been a drag queen,” she replied, before adding: “All I know about sex-change operations I’ve learned from my good friend Jason…”

Pirro appears to have remained part of Parton’s professional and personal orbit for decades. She thanked him by name in the liner notes of her 2016 album Pure & Simple for his “time, love, and attention to details”, and he later contributed to her 2023 book Behind the Seams, which chronicled her iconic career and wardrobe.

In 2023, as Tennessee lawmakers targeted trans people and gender-affirming healthcare, Parton was asked about the political attacks.

“I just want everybody to be treated good,” she said in a 2 November interview with The Hollywood Reporter. “I try not to get into the politics of everything. I try to get into the human element of it.”

She then made the personal nature of that position explicit, saying: “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 … all within my own family. I know and love them all, and I do not judge.”

‘I hope that everybody gets a chance to be who and what they are’

That philosophy also appeared in her response to North Carolina’s controversial 2016 anti-trans bathroom law.

“I think everybody should be treated with respect. I hope that everybody gets a chance to be who and what they are. I just know, if I have to pee, I’m gon’ pee, wherever it’s got to be”, Parton told CNN at the time.

For generations of LGBTQ+ fans, Parton became an icon partly because of this combination of warmth, humour and acceptance. She often avoided partisan political language, instead framing LGBTQ+ equality as a question of basic human dignity.

At a time when trans people were frequently sensationalised in the media and long before many celebrities were willing to publicly discuss transgender people or trans issues, Pirro was a trusted member of Parton’s world.

The surviving records don’t tell us everything about their relationship or exactly what Pirro’s role became over the following decades. But they do show she continued to acknowledge him publicly and privately, referred to him as a friend, and kept him in her professional circle for decades.

And perhaps most importantly, Parton’s own words about him were remarkably simple: Jason was her “good friend”.

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