Conan Gray is one of the lucky ones. He got his start as a teenager in Texas, documenting his experiences with AP art class and applying and eventually getting into UCLA on YouTube. Somewhere along the way, he began posting covers and eventually original music that outperformed his other content. His latest amphitheater tour is a far cry from his influencer roots, a household name who has escaped the “YouTuber” title. The “Wishbone Pajama Tour” is a 5-act production, including an encore, in support of Gray’s 5th studio album.
The show began with act i: a wishbone never breaks even. A windmill and mailbox bookended the stage. Conan Gray made a grand entrance on a bicycle with a note card in hand, which he ran to place in a mailbox, marked with Nashville and the date of the show. For the first few songs, Conan ran from end to end of the stage with an energetic and experienced presence. “Bourgeoisieses” brought a more sultry energy to the 26-year-old performer. This is a change of pace for the artist who has been quite vocal throughout his career about being a bit of a late bloomer. The opening notes of “Wish You Were Sober,” one of the big hits off of Gray’s debut, sent the crowd into a frenzy.
Conan’s live set brought more of a rock energy to his classic pop hits, a refreshing spin, without losing the familiarity fans have with the music. The staging evolved continuously, a boat and a bed were brought in and out, and Conan had a wealth of costume changes. The setlist was flawless, with a perfect mix of ballads and high-energy records as well as hits and B-sides. In act iii, Conan gave a fan in the crowd, coincidentally named Gray, the opportunity of choosing a B-side to add to the set by breaking a wishbone.
Before his platinum hit, “Heather,” Conan apologized to the namesake of the song, before retracting it because “this song is a f***ing banger.” The crowd erupted in laughter as he began playing an alternate version of the song. Before taking his final bow, Gray donned a glittery military outfit, a regal end to a beautiful set. His rough childhood has transformed into a dazzling, theatrical live experience that satiated fans both old and new. With a production that’s equal parts intimate storytelling and arena-ready spectacle, it’s hard to believe that he wasn’t born a pop star.
GALLERY: Conan Gray at Ascend Amphitheater in Nashville, Tennessee (September 24,2025)
