Kenny Chesney Remembers 'Terrible Loss' Of Beloved Dog In Emotional Moment

Kenny Chesney spoke about mourning the loss of his dog, Ruby, during a recent conversation with Anderson Cooper on his CNN podcast, All There Is.

Cooper shared a clip of his conversation with Chesney on Instagram on Tuesday (November 18). The 2025 Country Music Hall of Fame inductee said “it was really difficult” when he lost Ruby in 2022, “because we were a family. It’s a terrible loss.”

Cooper acknowledged that losing a pet is “a connection as strong as any other for many people.”

“When Ruby passed, it was really, really difficult. It was as terrible as any friend I’ve ever had that has passed,” Chesney said. Cooper played a clip of “Da Ruba Girl,” the song Chesney released in Ruby’s honor. The country megastar shared in 2022 that all proceeds from “Da Ruba Girl” would benefit Stray Rescue of St. Louis. He said at the time that he’s “very excited about that,” and “Ruby’s life gets to mean something. …Ruby’s life is gonna pay it forward, if you will, through this song. …I’m very, very proud of that.”

Chesney admitted it was an emotional moment when Cooper played a clip of “Da Ruba Girl” on All There Is. The singer-songwriter said, “I didn’t see this coming. I love it. You’ll see, this one’s gonna get me.”

“Ruby lived her life never holding anything against anybody,” Chesney wrote in his tribute to Ruby when he lost her in 2022. “She had an ancient, calming soul. She was honest and authentic, she was a protector, she took a warrior’s path in the journey of her life. Ruby loved the sun and how it felt on her face. She and I had that in common. Today I know Ruby is sitting somewhere with the sun on her face happy and grateful to have slipped her skin and body that was full of cancer. I know she is happy to have had Poncho in her life. They were partners in crime and never spent a day apart. But she is forever grateful that Mary saved her from the shelter. But really they ended up saving each other. I’m going to miss her, especially in the mornings. That’s when she and I really connected. So bye-bye, Ruby. You were a very good girl. We loved you and thank you for teaching us how to love unconditionally. You were one heaven of a dog.

“Losing Ruby has left a hole there are no words for,” Chesney added when he released “Da Ruba Girl.” “To honor her life, it only makes sense to let ‘Da Ruba Girl,’ the song she inspired, pay it forward by helping the incredible people at [Stray Rescue of St. Louis]. Ruby was everything good, and in her memory, this is her way of continuing to give and bring love where it’s most needed.”

Throughout his conversation with Cooper, Chesney also spoke about his lasting connection to a Sandy Hook family, grieving the loss of friend and legendary songwriter Brett James, and more. Find the full conversation here.