Kacey Musgraves Recalls Bringing Her Actual Grandpa to 'Fantasy Grandpa' Willie Nelson's Poker Night

Kacey Musgraves is sharing stories about time spent with a country legend.

On an April 20 episode of the Texas Monthly podcast One By Willie, the musician recalled a time "several Christmases ago" when she vacationed in Hawaii with family and brought her real-life grandpa to one of Willie Nelson's star-studded poker nights at his home.

While on a trip to Maui around four years ago, Musgraves says she booked a spot to stay with her family that happened to be close to the 88-year-old "Whiskey River" musician and his wife, Annie D'Angelo. One night, the "High Horse" singer was invited to Nelson's home for his son Lukas's birthday and soon joined a poker match in his game room.

"First off, it was really cute — Owen Wilson was there," the country star, 33, detailed of the evening. "Flash forward, we're just like hanging out. Willie has this, like, amazing poker room in the back. He and his buddies get out there every night and they play poker and listen to music, a lot of Willie's music, which I think is so baller. You're just like playing poker, passing around joints, and listening to your own music. It's kind of amazing — like, why wouldn't you?"

At one point during the hangout, Musgraves remembers seeing a familiar face but not quite knowing who the person was, so she decided to introduce herself.

"So I turn and introduce; I'm like, 'Hey.' I was like, 'What's your name?' And he said, 'My name's Paul.' And I said, 'Nice to meet you, Paul. I'm Kacey,'" she told the podcast. "And he said, he shook my hand and said, 'Nice to meet you too.' And then we turned back around and faced the poker game. In about two minutes, it kinda dawned on me that that was motherf—ing Paul Simon."

Nelson was hosting another poker night the following evening, so Musgraves asked if she could bring her grandpa, Darrell, an avid player of the card game.

"So, I was like, this would be crazy to see, like, who would win. My actual, real-life grandpa or my, like, fantasy grandpa, Willie Nelson," said the Star-Crossed performer, noting the Grammy-winning country icon said "Sure," but informed her the "buy-in" was going to be $300. "I went to an ATM, I got out some money, and when I got home — like I said, it was almost Christmas — I handed Pop a wad of cash, and I said, 'Merry Christmas.'"

Musgraves admittedly felt "so nervous" to bring her grandfather into the mix, as that night's group of players included Emmy-winning actor Woody Harrelson, but her "Pop" was up for the challenge. "He loses all of his money, and then he eventually wins it all back, and then he stood up and said, 'Well, I got to go.' And he ended on a high note," she explained. "So it was like, 'Holy s—, this is actually really happening.' He like, he lost to Willie, and then beat Willie's ass, and then we left."

"And then my grandpa, of course, was like the talk of their little Texas town," Musgraves told One By Willie, concluding the story. "He was like, all of his friends were so jealous. It was really cute."