Dolly Parton paid for the gender-affirming care of her 'good friend' & chauffeur of 30 years

Just when you thought Dolly Parton couldn't be any more sainted, her death at the age of 80 last week surfaced a story that makes it so. One of the most important staffers among Parton's close circle of supporters was a transgender man. Jason Pirro met Parton in the 1980s when he found himself chauffeuring the singer on a trip to Los Angeles. His clients already included Farah Fawcett, Kris Kristofferson, Willie Nelson, and Bewitched's Elizabeth Montgomery. The driver, who at 300 pounds cut a memorable figure in his chauffeur's tuxedo uniform, would work with Parton for over 30 years in that role and others, and become someone the singer described as her 'good friend.' Pirro first came to public notice in 1990, when the Star tabloid outed him on a cover. Splashed across a photo of Parton in signature rhinestones — and looking uncharacteristically fraught — the headline blared 'Sex change shocker in Dolly's limo' and 'Her driver is a man who used to be a woman.' The story inside belied the sensational windup. 'Dolly Parton is being chauffeured around Hollywood by a 300-lb. transsexual who has had an operation to change from a woman into a man,' the not-so 'shocking' story starts. 'The country queen shares 44-year-old Jason Pirro's 'secret' and has promised to help the obese, tuxedo-outfitted driver attain his goal to become a movie director.' 'Dolly has been good to me,' Pirro told the Star in an exclusive interview. 'I'm not real comfortable talking about myself. Dolly knows all about me and is a very nice lady.'' In a post last week, Parton's editor for her autobiography revealed the singer would go on to pay for Pirro's gender-affirming care. A post shared by Elissa Altman (@elissa_altman) The Star story may or may not be the source of a memorable line from the singer, affirming her longtime allyship with the trans and LGBTQ+ community. 'Dolly has said that there's nothing wrong with transexuals,' the Star story quoted the singer. ''If I were a man, I'd be a drag queen,' she admits. 'I enjoy being a trashy dresser and I love gaudy things. I love to play with hair and makeup,'' the story reported. Other facts about Pirro revealed in the Star exposé: he studied theater as a 'coed' at Syracuse University but left after eight years without graduating; he had a 'genius' IQ of 144; he taught Transcendental Meditation. Dolly likely had a lot of questions on the pair's rides between studios. In that same 1994 memoir, she shared, 'All I know about sex-change operations I've learned from my good friend Jason.' While Pirro's name surfaced again a few times over the years — Parton thanked him in liner notes for her 2016 album Pure & Simple for his 'time, love, and attention to details,' and he contributed to her 2023 book Behind the Seams about her extravagant wardrobe — their relationship was out of the spotlight of Parton's very public career, even as she championed for his rights. 'Well, what I always say, 'I just want everybody to be treated good,'' she told the Hollywood Reporter in 2023, as Tennessee was enacting discriminatory legislation against the trans community. 'I try not to get into the politics of everything. I try to get into the human element of it. 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,' Parton said. North Carolina's notorious bathroom bill in 2016 elicited a similar defense, and a characteristic, apolitical rejoinder: 'I just know if I have to pee, I'm gonna pee. I don't care where it's going to be,' she told The Tennessean. In that same interview, likely with Pirro in mind, Parton declared, 'I think everybody should be treated with respect. I hope that everybody gets a chance to be who and what they are.'