In the week or so since Dolly Parton’s death, stories about the country music legend’s longtime support for the LGBTQ+ community have resurfaced. One of them centers on someone who worked alongside her for more than three decades.
Jason Pirro, a transgender man, worked with Parton in several roles over the years, including as her chauffeur, assistant and photographer.
By 1987, Pirro was already part of Parton’s professional circle. He was included in the special thanks for her album “Rainbow,” and credits for Parton’s 1987–88 ABC variety series “Dolly” list him as an assistant to Parton on six episodes.
Three years later, Pirro’s gender history became public when a supermarket tabloid known as Star published a story about him. An August 1990 issue of Twenty Minutes, a newsletter for the transgender community, reported on the story and reproduced comments attributed to Pirro.
“Dolly has been good to me,” Pirro said at the time. “Dolly knows all about me and is a very nice lady.”
Pirro, who was 44 at the time, also described his work driving Parton when she was in Hollywood.
“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,” he said.
The surviving accounts don’t answer some of the more interesting questions about their relationship. It’s unclear how Pirro first came to work for Parton, whether she knew he was transgender when she hired him or when she learned. Pirro’s comments do establish that she knew by 1990.
Following Parton’s death, a man identifying himself as Pirro’s cousin offered another glimpse into their long working relationship. In a Facebook post, Joe Pirro said his cousin had been Parton’s personal assistant for 40 years.
“She is everything you hope she would be — caring, generous, loyal, smart, and funny,” he wrote.
Parton mentioned Pirro several times in her 1994 memoir, “Dolly: My Life and Other Unfinished Business.” While answering a question about drag performers, cross-dressing and people who had undergone gender-affirming surgery, she referred to him as her “good friend Jason.”
“All I know about sex-change operations I’ve learned from my good friend Jason,” Parton wrote.
Pirro continued working with Parton in the years that followed. He received a photography credit on her 1998 album “Hungry Again” and was thanked for his “time, love, and attention to details” in the liner notes for her 2016 album “Pure & Simple.”
His name was still connected to Parton’s work decades later. Pirro contributed to the audiobook edition of her 2023 book “Behind the Seams: My Life in Rhinestones,” where he was included among a group described as Parton’s “lifelong fashion collaborators.”
By then, Parton was also speaking publicly on behalf of transgender people.
In 2016, as North Carolina faced national backlash over House Bill 2 and its restrictions on transgender people’s access to public restrooms, Parton said she believed “everybody should be treated with respect.”
“I hope that everybody gets a chance to be who and what they are,” she said. “I just know if I have to pee, I’m gonna pee. I don’t care where it’s going to be.”
Parton returned to the subject in 2023 when The Hollywood Reporter asked her about legislation targeting transgender people in her home state of Tennessee.
“I try not to get into the politics of everything. I try to get into the human element of it,” Parton said, explaining that LGBTQ+ people were among her family and circle of employees.
“I know and love them all, and I do not judge,” she said.
According to public records, Pirro is now 80 and maintains a residence in Canoga Park, California. He has made no known public statements about Parton since the Star article over 35 years ago.
This story is brought to you by Rosedale Health and Wellness and Dudley’s Place.
