Besides their big personalities and even bigger careers, both ladies have faced longstanding rumors of being secretly gay (Winfrey with her pal Gayle King and Parton with her childhood friend Judy Ogle).
"We do talk about that," Parton told ABC News of bonding with Winfrey over the false fodder.
"Gayle, her friend, Judy, my friend, they just think that you just can't be that close to somebody," explained the 66-year-old music legend. "Judy and I have been best friends since we were like in the third and fourth grade...I love her as much as I love anybody in the whole world, but we're not romantically involved."
Not that Parton has anything against the gay community. The camp-glam singer recounted a time when she actually entered a celebrity lookalike contest posing as a drag queen...and lost!
"They had a bunch of Chers and Dollys that year, so I just overexaggerated," she said. "Made my beauty mark bigger, the eyes bigger, the hair bigger, everything.
"All these other beautiful drag queens had worked for months and weeks getting their clothes and they were dressed like me. So I just got in the line and I just walked across, and they just thought I was some little short gay guy...but I got the least applause but I was just dying laughing inside."
Parton added with a laugh, "I say, it's a good thing I was a girl or I'd be a drag queen!"