Colbie Caillat Surprises Crowd With Gavin DeGraw, Ashley Cooke, Brett Young

Colbie Caillat surprised the crowd with several special guests during a recent rooftop show in Nashville, Tennessee.

The Grammy Award-winning singer-songwriter delivered surprise duets with Gavin DeGraw, Ashley Cooke and Brett Young as she performed music spanning her career last month. Caillat’s set included everything from her most recent album, Along The Way, a 13-track record that arrived in October 2023, to tracks that have long been fan-favorites from her debut album, Coco. The 2006 collection included breakthrough hit “Bubbly,” along with “Realize” and other highlights. That album paved the way for Caillat’s genre-transcending success with singles like “Fallin’ For You,” “Brighter Than The Sun,” “Try” and many others. The Rooftop on the Row show also included singer-songwriter Ryan Larkins, whose set included covers of Garth Brooks’ “Friends In Low Places” and Cody Johnson’s “The Painter,” in addition to originals like “King of Country Music.”

Caillat teamed up with “In Love With a Girl” hitmaker DeGraw on a duet of “I Never Told You,” from Caillat’s 2009 album, Breakthrough. She welcomed reigning CMT Music Awards Breakthrough Female Video of the Year winner Cooke to the stage to perform “mean girl,” the duo’s collaboration that appears on Cooke’s debut album, shot in the dark. Cooke, iHeartCountry’s On The Verge Artist, released the 24-track collection last summer. She surprised an intimate audience with Caillat during an exclusive album preview event. Cooke said at that time that as a longtime fan of Caillat’s, she was “so excited” to write a song together and “create something really special.” Cooke also included a collaboration on her album with Young, who joined Caillat to perform “Worth It” during her rooftop performance in Midtown Nashville. That’s one of the Along The Way tracks Caillat said she’s particularly proud of because of its post-breakup perspective.

“I will say this is my favorite album I’ve ever written and recorded,” Caillat said of Along The Way in a recent interview with iHeartRadio, ahead of the recent Power of Love gala honoring country megastar Blake Shelton. “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 described herself in that interview as “introverted” and “shy.” That’s why she appreciates the opportunity to get vulnerable in her songwriting, and share those experiences with listeners and live audiences. She said songwriting “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. …that’s what music does. It makes you feel like you’re not alone, and someone is speaking for the thoughts in your mind,” she said. “It’s very comforting.”