Dolly Parton and her trans chauffeur Jason Pirro: Remembering her LGBTQ+ legacy

Following Dolly Parton’s death on 25 August, fans are celebrating her LGBTQ+ advocacy, particularly her support for the trans community, as it has come to light that her long-term chauffeur and assistant, Jason Pirro, was transgender.

Pirro worked as Parton’s chauffeur and reportedly remained a close friend and colleague for around 40 years. Parton knew he was transgender and, according to archival interviews, treated him with the utmost respect.

A 1990 issue of the transgender newsletter Twenty Minutes reported on Pirro’s relationship with Parton, reproducing quotes from his interview with the Star for a July 1990 report.

“Dolly has been good to me” – Jason Pirro on his relationship with Dolly Parton

Here's the text of the original Sun interview with Pirro https://t.co/vgTD1KYGxr pic.twitter.com/XAdWWGvcVo

— Gillian Branstetter (@GBBranstetter) August 25, 2026

Pirro told the Star: “Dolly has been good to me,” adding: “I’m not real comfortable talking about myself. 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.”

He had reportedly undergone gender-affirming surgery and changed his name in the 1980s. A family friend described Pirro as “a loving, warm, caring human being”. They added: “He teaches transcendental meditation. He has never had an enemy. People just take a liking to him.”

Parton name-checks Pirro in her 1994 memoir, Dolly: My Life and Other Unfinished Business

In her 1994 memoir, Dolly: My Life and Other Unfinished Business, she discussed her views on drag and trans people, famously saying: “Well, I’ve always said that if I hadn’t been a woman, I would have been a drag queen.”

She also name-checked Pirro, revealing that he had educated her about gender transition: “All I know about sex-change operations I’ve learned from my good friend Jason.”

In 2023, she drew attention to the LGBTQ+ people in her life, including colleagues, family members and fans. Speaking to The Hollywood Reporter, she said: “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.”

She continued: “I know and love them all, and I do not judge… That’s who they are. They cannot help that any more than I can help being Dolly Parton.”

Parton’s support for the trans community extended far beyond her personal relationship with Pirro, with her music and advocacy repeatedly embracing LGBTQ+ people.

Parton’s history of trans advocacy

She famously wrote ‘Travelin’ Thru’ for the 2005 film Transamerica, which follows a transgender woman travelling across the US with the son she has recently reconnected with.

Parton also spoke out against restrictions targeting transgender people, particularly when North Carolina introduced its controversial anti-trans bathroom law in 2016.

Speaking to CNN at the time, she said: “I think everybody should be treated with respect… I hope that everybody gets a chance to be who and what they are.”

In 2023, Parton was asked about anti-trans laws introduced in her home state of Tennessee, including a ban on gender-affirming healthcare for minors.

Parton told The Hollywood Reporter: “I just want everybody to be treated good… They cannot help that any more than I can help being Dolly Parton.”

The country music icon died peacefully at the Vanderbilt-Ingram Cancer Center in Nashville, Tennessee.