Dolly Parton’s chauffeur and assistant of 30+ years was a trans man she supported and loved

This story originally appeared on Them.

As the world is still reeling from the news of the death of legendary Queen of Country Music Dolly Parton on Tuesday, many of her LGBTQ+ fans have resurfaced evidence of her long and enduring support of the LGBTQ+ community.

That support included a job and a lasting friendship with a transgender chauffeur, Jason Pirro, who previously spoke with the press about Parton, saying that the singer “knows all about me and is a very nice lady.”

Twenty Minutes, a transgender newsletter that circulated in the late 1980s and early 1990s, wrote about then 44-year-old Pirro in its August 1990 issue, pulled from a story in which the tabloid Star spoke to Pirro about his relationship with Parton.

The newsletter item gained renewed traction on social media following Parton’s passing when it was shared by writer Gillian Branstetter, who works as a communications strategist for the American Civil Liberties Union but posts online in a personal capacity.

Per Twenty Minutes, Parton was then being “chauffeured around Hollywood” by Pirro, whom the newsletter claims “had an operation to change from a woman into a man” — most likely language pulled directly from the Star article, though the contents of that issue were not immediately available for independent confirmation that it is a reprint.

The cover of that particular issue of Star — dated July 10, 1990 — remains online, however. In one eBay listing, the headline reads: “Sex change shocker in Dolly’s limo,” with a subheadline stating: “Her driver is a man who used to be a woman.”

The Twenty Minutes issue highlighting the Star article remains widely accessible through the Digital Transgender Archives, an online hub of materials meant to preserve trans history. That newsletter itself is housed in the Sexual Minorities Archives in Holyoke, Massachusetts, which also holds the research materials of late trans author and activist Leslie Feinberg.

In quotations selected from Star, Pirro seems to suggest that Parton was aware he is a transgender man. “Dolly has been good to me,” Pirro told Star, according to Twenty Minutes. “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.”

Though the article does deadname Pirro, it mentions that he had gender-affirming surgery and changed his name in the 1980s. It also claims he has a “genius-level I.Q. of 144.”

“He’s a loving, warm, caring human being,” a family friend told the tabloid. “He teaches transcendental meditation. He has never had an enemy. People just take a liking to him.”

A 1990 issue of prominent trans author Lou Sullivan’s newsletter also included an item about Pirro based on the Star interview, per a post on the Tumblr TransGuyArchive. That blurb claimed that Pirro had also worked as a driver for Farrah Fawcett, Kris Kristofferson, and Willie Nelson.

In her 1994 memoir, Dolly: My Life and Other Unfinished Business, Parton mentions Jason Pirro by name several times. When she gives “Special Thanks” to loved ones, she includes him by first and last name, per a copy of the book accessed through the Internet Archive.

She also mentions him in the book’s final section, a transcript of a Q&A in which Parton touches on many topics, including her support for LGBTQ+ people. (Per a note from Parton at the top of the chapter, these questions were sourced from a variety of people.)

“What do you think of female impersonators, transvestites and people who have sex-change operations?” one person asked Parton.

“Well, I’ve always said that if I hadn’t been a woman, I would have been a drag queen,” Parton started out. “I have seen men impersonate me, and I consider it flattering. I especially like it on Halloween. Then I can go anywhere in Hollywood and never be noticed.”

She continued, “All I know about sex-change operations I’ve learned from my good friend Jason…”

Pirro appears to have continued working for Parton in a capacity beyond being her driver for several decades, based on social media posts and various credits and acknowledgments. Parton thanked him for his “time, love, and attention to details” in the liner notes to her 2016 album Pure & Simple — and Pirro recently contributed to Parton’s 2023 book Behind the Seams, an illustrated look back at her legendary career.

Them reached out to Pirro and will update this story if we hear back.

Parton’s advocacy for trans people extended into politics — in her distinct, often universalizing way. In 2016, when North Carolina passed its controversial HB 2 bathroom bill, Parton stood with trans people.

“I think everybody should be treated with respect. I hope that everybody gets a chance to be who and what they are,” she said at the time, per the Knoxville News Sentinel. “I just know if I have to pee, I’m gonna pee. I don’t care where it’s going to be.”

In 2023, when trans people faced attacks in her home state of Tennessee, including a ban on gender-affirming care, she was also outspoken in her support.

“Well, what I always say, ‘I just want everybody to be treated good,’ she told the Hollywood Reporter. “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.”

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