Conan Gray’s Oct. 3 “Wishbone Pajama Tour” stop was a concert that felt like diary entries coming to life — a staged dream sequence at Shoreline Amphitheatre, where heartbreak, nostalgia and yearning unfolded with the polish of a Broadway production and the sincerity of a bedroom confession.
Even before Gray appeared, the audience was electric. Fans donned pajamas and sailor costumes (a reference to the “Wishbone” album aesthetic), screamed lyrics to the pre-show playlist and erupted into spontaneous standing ovations with the mere flicker of the lights. When Gray’s opening act, indie artist Hemlocke Springs, emerged in a purple corset to match her purple-streaked hair, the crowd welcomed her like a returning friend. Her quirky stage presence and infectious energy carried through her viral hit “girlfriend,” which sent the amphitheater into its first collective singalong of the night. By the end of her set, she’d earned one of the rare honors for an opener: a standing ovation from the audience.
Then the stage darkened, and the words “Act I: a wishbone never breaks even” glowed across the back screen. Gray rolled in on a bicycle, grinning as his band, dressed in matching uniforms, launched into “My World” and “Never Ending Song.” The crowd’s scream was instant and deafening.
The set was equal parts concert and coming-of-age. A patch of grass spread across the stage, dotted with clouds and a bed that Gray would later roll out for a costume change — slipping into a pajama set mid-show, as if inviting us deeper into his dream world. Between acts, the stage transformed through sound and color: birds and cicadas chirped through transitions, and blue and yellow papers fluttered like petals as Gray strummed an acoustic guitar marked with a painted wishbone.
Act II, “I got the short end of the stick,” leaned darker, stretching across the heartbreak’s raw edge. Gray’s voice, delicate but cutting, carried through “Class Clown,” “People Watching” and “The Cut That Always Bleeds,” songs that felt less performed than intimately confessed. Yet amid all the theatrics, there was still warmth — in the crowd harmonies, in Gray’s small smiles when fans sang back every word and especially in his mid-show message: “If you don’t feel loved, know that you are loved by me.”
Each act deepened the narrative. By Act III — “I took the long way to realization” — a boat had appeared onstage, and Gray, now in a sailor costume, seemed to steer through his own emotional reckoning. He paused to invite a fan celebrating their birthday onstage, offering them the chance to “break” a wishbone and choose the next song. The fan’s winning pick — “Care” — became a moment of shared catharsis, Gray hugging them tightly before launching into the chorus. Then came “Heather,” the song that cemented Gray’s rise from bedroom pop to mainstream voice of heartbreak. When he reached the line “Why would you ever kiss me?”, the entire amphitheater echoed it like a collective confession — one of those rare, suspended concert moments where no one’s pretending to be fine anymore.
The final act, “I wished for love, and I found it,” offered something softer, lighter, not resolution, but release. Gray reemerged in a sailor-style ensemble for “Maniac,” dancing with playful abandon as the crowd bounced along. “Vodka Cranberry” followed, a bittersweet anthem of letting go, its self-aware humor underscoring just how far Gray has come from the quiet longing of his first album, “Kid Krow.”
As the stage glowed with soft pinks and golds, Gray named his band one by one in appreciation before heading offstage… only to return moments later in a sequin-encrusted nutcracker suit for the encore. “Memories” and “Caramel” shimmered with nostalgia and relief, closing the night with that rare mix of ache and uplift that defines his artistry.
I cannot say I consciously had any expectations going into Gray’s show. But after reading Arts & Life columnist Audrey Chang’s review of “Wishbone” and seeing Gray live, it seems that the raw emotion conveyed through his lyrics is precisely what he delivers on stage. If Gray’s early music captured the ache of youth, his Wishbone Pajama tour shows him reimagining that ache as something to stage, share and celebrate. His show at Shoreline wasn’t about mending a broken wishbone: it was about finding beauty in the uneven pieces.