Country superstar Kenny Chesney sat down with Anderson Cooper for an emotional new episode of CNN’s All There Is podcast this week, where the two reflected on grief, friendship, and the power of music to connect people through loss. In one of the most moving parts of the conversation, Chesney opened up about his enduring relationship with a Sandy Hook family whose late daughter, Grace, was a huge fan of his.

During the interview, Cooper recalled how he first introduced Chesney to the McDonnell family in the days following the 2012 tragedy.

“Before that interview, I was in their kitchen,” Cooper said. “This was just days after their daughter was killed. There was a photo of you on the refrigerator. I said to Lynn, ‘Oh, do you like Kenny Chesney?’ And her eyes lit up and she said, ‘Grace loved Kenny Chesney. The morning she was killed, we were waiting for the bus, singing one of his songs.’”

Cooper said he texted Chesney that night, letting him know how much his music had meant to the family.

“You texted me right back and said you wanted to reach out to Lynn,” Cooper continued. “You called her, and you spoke for a long time.”

Chesney recalled that moment vividly and said the connection has lasted for years.

“Yeah, and we have since then become really good friends,” Chesney said. “I can’t tell you how many shows her and Chris have come to over the years. They actually brought me a piece of art that Grace painted and gave it to me. I had it framed, and it was in my bus for years.”

Chesney then noted an extraordinary coincidence, based on the day the podcast was recorded.

“Today’s November 4 — the day my book comes out — and it’s Grace’s birthday. She would have been 20 today,” he told Cooper. “I get chills thinking about it.”

As the two reflected on the power of compassion, Cooper praised Chesney for staying connected with Grace’s mother, Lynn, over the years.

“There’s not a lot of people who would have reached out in the worst moment of her life and kept in touch,” Cooper said.

Chesney replied, “You just try to be there for them. There’s not a lot to say. I can’t imagine being a parent and that happening. She told me things about Grace that made me feel incredible — how much she loved the music, how much the family would go to the beach and listen to it. When Grace passed, they had ‘No Shoes, No Shirt, No Problems’ written on the casket. I just think it’s unbelievable that we’re having this conversation on what would’ve been her 20th birthday.”

Later in the episode, Chesney also spoke about losing his longtime friend and songwriting partner Brett James, who was killed in a plane crash earlier this year.

“I’ve lost someone recently, someone that I created with for a very long time,” he said. “My friend Brett James, who was killed in a plane crash a couple of months ago. It’s been hard because we were brothers and songwriting partners… his creative soul changed my life.”

He described how emotional it was to perform one of James’ songs live for the first time after his passing.

“The first time I sang one of his songs after he passed was at Farm Aid with Willie Nelson in Minneapolis. I was going to do ‘When the Sun Goes Down,’ which he wrote by himself, and all of a sudden, the wound was really open. But I’m going to keep singing it — in a celebratory way now,” said Chesney.

“Brett was just one of those guys I thought would always be around,” he continued. “And with Grace and her family, I’ve learned how much music can matter to people in ways you never expect. You just try to be there — for them and for the song.”