It makes perfect sense that Dolly Parton and Willie Nelson would be close friends. One is a brilliant and prolific songwriter, country music legend, fashion maverick, and adored by basically everyone. And the other is — also a brilliant songwriter, country legend, fashion maverick, and universally adored.

Parton gushed about the American icon to WSJ Magazine, “Willie’s loved because he’s a great person, he’s a great man, He’s honest, he’s fair, he’s very generous – he’ll sing with anybody that wants him to, he’ll just do anything. He’s got a good heart.” She didn’t skimp on praise for his work as an artist either, or how he’s come to represent America.

“That headband he wears, for one thing, and the dope he smokes, and the songs he writes, and the fact that he’s just down to earth, good ol’ boy, everybody relates to him,” she said. “High-class people relate to him because of his true musical gift — he can sing anything, he just has a Frank Sinatra album out now, and the ‘Stardust’ album, so you know he can sing anything from ‘On the Road Again’ to any choice of songs. But Willie is just likable, he is just an all-American boy — he’s from Texas and he acts like it.”

Obviously, we just had to dig deeper into the bond between these two.

The pair go way, way back

Dolly Parton is never shy when it comes to talking about her pal Willie Nelson, digging into how they got their start at around the same time in Nashville, and the many ways they’re so similar (the hair, for one thing).

“Willie and I came to town about the same time,” Parton said in a 2014 interview with CMT. “Back in 1964, ’65, ’66, we both were writing for Combine Music.”

She even hinted that there might have been a little love (missed) connection. “I think he’s a character, and when we got ready to do the song, Willie called me,” she said, referring to their duet recording of Parton’s “To the Moon and Back” on Nelson’s 2013 duet album. “He was doing his album, ‘All the Girls He’d Loved Before’ or ‘Made Love To,’ I don’t know. … I was one of the girls he loved. We never had a thing going. It’s a wonder, though.”

It doesn’t look like he’s bitter about it, though. As Parton recalled in a different interview in 2020, she asked her old friend to duet with her for her Christmas album — particularly, on the song “Pretty Paper.” He replied, “I could not do a Christmas album at this time without doing this song. Aw, hell, you think you gotta ask me that? Of course, I’m gonna sing a duet with you on it.”

Gotta love old friends.

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