Inside Jimmy Fallon And Dolly Parton's Relationship

Sometimes, it seems like Dolly Parton is one of Jimmy Fallon's favorite guests on "The Tonight Show." Whenever the legendary country singer, entrepreneur, and all-around entertainer appears on Fallon's late-night gabfest, she never fails to make the host crack up because she always has something shocking to say or do.

In fact, there seems to be a mutual admiration society going on between this talk show host and his frequent guest, who tells elaborate stories that sometimes don't even turn out to be true. In an October 2021 People interview, Parton confessed how she really feels about Fallon. "Well, I have a crush on Jimmy Fallon, but I'm big now, I can't excuse myself on that! I think he is precious," she said. "He's so funny. We get along so good." 

So how and when did this crush begin, and how has Parton thrilled Fallon over the years through her various guest appearances? Read on to find out.

Dolly Parton made Jimmy Fallon blush with a Jennifer Aniston story

During one of Dolly Parton's appearances on "The Tonight Show" in 2018 (via YouTube), she used a racy story about her husband, Carl Dean, to make Fallon blush. Parton was promoting the music she wrote for Jennifer Aniston's latest movie at the time, "Dumplin'," the story of a plus-size daughter of a former beauty queen who decides to join the pageant circuit (via IMDb). Just the idea of his wife doing anything with Aniston apparently thrilled Parton's longtime husband. 

"He was more excited that I was gonna do a movie with her than he was [about how] I got the chance to write all this music," she said. "I think he kinda fantasizes like a threesome with us." As soon as Parton mentioned the threesome, Fallon tried to cut to the band, but Parton had more to say. "But I'm serious, he does," she said. "I think he can't even get it out to pee much less get it up for three." That's when Fallon couldn't take anymore and dropped straight to the floor, looking like he was about to crawl away.

When Fallon did eventually get it together, he expressed his joy at having Parton there. "I just love you so much," Fallon said. "And I can't tell you ... how nice you are, in real-life, in person ... You're Dolly Parton, you can do whatever you want, but you're so nice to everyone."

Dolly Parton pranked pal Jimmy Fallon

During a 2019 "The Tonight Show" appearance (via YouTube), Dolly Parton made Jimmy Fallon roll with laughter once again with an alleged childhood story.

The story involved Parton taking her family for pancakes as a teen with some money she earned from her songs. "Once when I took them up there, we were in the restaurant and we were having our meal, and then this old man came over to our table," she recalled. "He sat down, and he was just talking to us and we were all laughing. We didn't know him."

However, the man apparently told the restaurant owner that he was Parton's grandfather and left his bill for her to pay. She realized she'd been scammed, paid the bill, and then confronted the man in the street, she said. "I went over to him and said, 'I would have been happy to have paid your bill, but telling them that you're my grandpa ... ' And he took his walking stick and he started just beating me across the chest. Just as hard as he could ... And it hurt."

Fallon could barely believe his ears and asked what happened next. That's when Parton stood up, showed off her chest, and said, "What do you mean what happened? These two big lumps came up and never did go down!" Parton then laughed and simply said, "Gotcha," leaving Fallon in stitches.

Dolly Parton and Jimmy Fallon offered holiday cheer

Everyone needed a little cheer near the end of 2020 after the COVID-19 pandemic threw the world for a loop and turned everyone's lives upside down across the globe. In October 2020, Dolly Parton released a new studio album, "A Holly Dolly Christmas," featuring a lovely duet with Jimmy Fallon of Mariah Carey's hit "All I Want for Christmas."

In the official video for the song (via YouTube), the two entertainers even engage in a little playful banter. "I don't know how to say this without sounding all mushy and romantic," Parton said, to which Fallon replied, "I kinda like mushy and romantic."

Perhaps the idea for the recording came from that same "Tonight Show" appearance when Parton told Fallon the story about her husband wanting a threesome with Jennifer Aniston. After Fallon recovered from his laughter, the pair took to the mic and performed a Christmas medley, spreading their signature good cheer (via The Boot).