Ryan spilled on the hilarious story when he stopped by TooFab earlier this week. According to the heartthrob, Billy was so on board with him meeting Miley that he invited him over to stay in a tent he had pitched on the front lawn of his Tennessee home.
"One of my favorite stories was I was in Nashville, I think, and I was playing a show," Ryan told us. "And Billy was like, 'Hey! I'm at the ranch!' It was like 30 minutes outside Nashville or something. And he was like, 'Just come! Stay at the house! I set up tents in front of the house. Miley's gonna be there.' I'm like, 'Billy, I got my tour bus right here. I think I'm good about staying on your front lawn.'"
"But Billy was like, 'C'mon, Ryan! Please? Just stay in my tent!'" Cabrera laughed as he broke out his best Billy accent. "I was like, 'No, Billy. I'm good. Thanks for the invite.'"
"We actually ended up going to the set," Ryan continued. "This was like 'Hannah Montana' days. They were filming ['Hannah Montana: The Movie].' And I had saw, somebody sent me Miley, I guess when she was, I forget what age, but her celebrity crush. They asked her celebrity crush, and she said, 'Ryan Cabrera.' And so I was friends with Billy, and Billy was like, 'You have to come meet Miley. You're her celebrity crush. We'll embarrass her! Come on set of the movie. Sleep out in front in the tents. You can stay at the house!' I was like, 'I'll come say hi and hang out with you guys, but I'm gonna sleep on the bus.'"
"We all laughed about it. She laughs about it," Cabrera added. "And then I ended up becoming friends with Trace [Cyrus] and everybody, and they're all like the sweetest [people]."
Ryan went on to describe Miley as "hilarious," "very unique" and "super, super talented."
By the way, the celebrity crush quote was from 2008, when the then-"Hannah Montana" star told Us Weekly at the time, "Ryan Cabrera is really cute. He's a friend of my dad's!"
Meanwhile, during a conversation about "Live from Ryan's Living Room," Cabrera revealed one of his favorite guests was actually Billy, who appeared on his live-music, for-charity web series in December of last year. Cyrus sang his hit, "Achy Breaky Heart," as well as an off-the-cuff original, "In Ryan's Living Room." Together, they raised $24,000.
One week later, the country star's cameo on Lil Nas X's "Old Town Road" dropped -- and although Ryan had no idea the unsuspecting collab was even in the works, he thinks the country-rap crossover was pure genius.
"I was like, 'Gimme the heads up next time!'" Ryan joked. "He's had the No. 1 single, like, since then. I was so happy for him because he's such an incredible artist and just human being. Every time I've asked him to do something, he's like, 'For charity? I'm in. Let's do it, Ryan.' He's great. Very happy for him."