Conan Gray Breaks the Wishbone in Clarkston

Review and Photos by Danie Beaman

Conan Gray for the Wishbone Pajama Show in Clarkston, MI

The lights cut out, plunging the concertgoers at Pine Knob Music Theatre into darkness midway through Olivia Rodrigo’s bad idea, right?. Anticipation ripples through the crowd, excited screams and cheers filling the venue as the words “1. a wishbone never breaks even” appear on a screen through the darkness. A spotlight flickers on the drummer at the back, and suddenly the stage is engulfed in golds and pinks. Conan Gray pedals into view on a vintage-looking bike, donning a sailor’s uniform and hat, and parks his bike among the wheat field covering the stage. He reaches into the basket of his bike to find a postcard, and slides it into a mailbox marked “Clarkston, MI, 9/17/2025,” and turns, seemingly noticing the sea of faces in front of him for the first time.

Opener “hemlocke springs” began the night with a high-energy setlist, including songs such as “head shoulders knees ankles” and the TikTok viral “girlfriend.” She did an incredible job of hyping up the crowd before Conan’s set, amplifying the already intense energy of the concertgoers.

Conan Gray kicked off his show with “My World” from his latest album, Wishbone, drawing the crowd into his world. He smoothly shifted to songs from his previous three albums, including “Never Ending Song” and “Wish You Were Sober.” After changing out of his sailor suit and into sparkly striped pajamas, Gray took his first of two “naps” as the stage transformed into a cloud-filled dreamland, ushering in the show’s second act, titled “i got the short end of the stick.”

The show continues with more songs from all four of Conan Gray’s albums, including the emotional “People Watching” and “Nauseous,” before we are transported once again, this time to a lake. A boat is wheeled onto the stage, and Conan appears from behind it, wearing a new outfit reminiscent of a prince out of a storybook.

This change of scenery marks the third act, “i took the long way to realization,” featuring the show’s popular surprise song segment. Out comes a prop wishbone. One lucky member of the crowd gets to break the wishbone with Gray. The rules are simple: two song choices—”The Exit” and “Astronomy” for Clarkston, both from his sophomore album Superache. Whoever gets the long end of the wishbone picks the song.

That is, until Gray gets the long end of the stick. Despite his original rules, Conan Gray allows the fans to choose between the songs because, in his own words, he is “the nicest guy who was ever born,” a statement the crowd enthusiastically agrees with. At the fan’s choice, Gray plays “Astronomy,” tells the crowd that they are loved before playing the devastating “Family Line,” and concludes his third act with a segment fans have lovingly dubbed “the Connell crash-out.”

We are then brought into the fourth and final act of the Wishbone Pajama Show, set once again in that same field the show began in, titled “i wished for love, and i found it.” Songs from this high-energy act included hits “Maniac” and “Vodka Cranberry.” Gray then informs the crowd that he has reached his final song of the night, though this declaration is accompanied by comical blinks (yes, not winks) and nudges that suggest an encore.

Conan Gray comes back onto the stage for a final time, singing “Memories” and “Caramel” before closing out the show to thunderous applause.

Conan Gray’s Wishbone Pajama Show is an incredible, vulnerable experience from the up-and-coming singer. Everything from the stage design to the setlist to the crowd’s energy is something worth checking out. Only a few shows remain on the Wishbone Pajama Show Tour, so if Conan and his merry band of sailors are coming to your area, don’t hesitate to check it out!