Colbie Caillat is gearing up to honor longtime friend and beloved country star Blake Shelton, including with a cover of one of the Oklahoma-born artist’s career-spanning songs.

Caillat has known Shelton since his early days of coaching on The Voice, and reunited with him on his TV game show, Barmageddon, last year. Caillat knows Shelton as “hilarious,” and “one of the coolest guys.”

Shelton will be honored at the 27th annual Power of Love gala on Friday (May 10), hosted at MGM Grand Garden Arena in Las Vegas, Nevada. Keep Memory Alive announced the star-studded lineup of the fundraising event last month, including Caillat, Jay Allen, Kristin Chenoweth, Andy Grammer, Mickey Guyton, Gary LeVox and Cassadee Pope. The philanthropic event supports the Cleveland Clinic Lou Ruvo Center for Brain Health and its efforts to support those affected by Alzheimer’s, Parkinson’s and Huntington’s disease, multiple system atrophy and multiple sclerosis.

“I’ve always been a fan and friends with Blake Shelton, and I’m so happy that they’re honoring him, and I’m so excited I get to sing a couple songs — one of my own (‘Bubbly,’ and) one of his songs — and get to hear all the other artists that are playing,” Caillat said during a recent conversation with iHeartRadio. “I’m happy to be a part of it.”

Caillat has remained close to the country genre since the beginning of her Grammy Award-winning career, including by starting a country band (Gone West) and working with Nashville, Tennessee-based songwriting friends and collaborating with other artists. Recent collaborations include iHeartCountry On The Verge Artist Ashley Cooke, who teamed up with Caillat on “mean girl,” featured on her debut album, and Rock and Roll Hall of Fame inductee Sheryl Crow on “I’ll Be Here.” That duet appears on Caillat’s latest full-length album, Along the Way.

“I will say this is my favorite album I’ve ever written and recorded,” Caillat told iHeartRadio of the project she debuted in October 2023. “And I think because it’s a heartbreak album, but I really love the whole tone behind it. …I wrote it about how proud I was of the relationship that I was in, and although we’re not together, I still love the times we experienced and the love that we shared, and so my song ‘Worth It,’ I love for that reason. The songs I wrote by myself I’m really proud of. ‘Blue’ and ‘Two Birds’ and ‘Old & New.’ It’s kind of rare when I write by myself, so I was really proud of those.

“When you write a song by yourself, obviously you get the song that you create,” she continued. “But when you write with different people, you get different perspectives and different outlooks and experiences. And then add on a voice that you love and making it a duet and adding those harmonies and different vocal tones, it makes it so much fun.”

Caillat embraces the moments she can observe the audience’s reaction when she can surprise them with a special guest, or begins playing some of her biggest, career-spanning hits, including “Bubbly,” “Try” and others. She said it “it makes me happy to be able to play these songs, and reminds me why I wrote them, and why I’m out there performing,” including with upcoming appearances at CMA Fest and other music festivals on the horizon. The Grammy winner wrote her first song when she was 19 years old, after her first guitar lesson, and “because I actually knew so little on guitar, it made me have to get more creative vocally.” Caillat credited her parents with being “right,” when they encouraged her to pick up an instrument. Now, she sees songwriting as “so therapeutic.”

“That’s something that I’ve always loved, and I would’ve thought — because I’m very introverted, I’m shy, I’m reserved a lot of the time. But when I get to write songs, I like that I get to be vulnerable and share what I’m going through, and I’m excited for people to hear them or to play them live,” Caillat said of expressing herself and connecting with others through songwriting. “It connects us all. It’s so cool to see the audience listening to those songs, listening to the lyrics (and) either crying because it fills their heart or makes them feel like they’re not alone going through a loss or a breakup. And I’m like, ‘wow, I thought I was alone in whatever I was writing about,’ and these people probably felt like they’re alone in what they’re feeling right now in what they’re going through in life. And it — that’s what music does. it makes you feel like you’re not alone, and someone is speaking for the thoughts in your mind, and it’s very comforting.”

Noah Kahan - "Stick Season"

Harry Styles - "Daylight"