BY Madison Hill | September 18th, 2025
“Coneheads” nearly sold out the Petersen Events Center on September 16th to see Conan Gray’s Wishbone Tour. It’s been a long journey since Conan was first posting music on YouTube, but that early connection with fans is still there. With Kid Krow and Superache behind him and Wishbone just released, Pittsburgh was the next stop on his sixth headlining tour.
Fans dressed the part for the “pajama tour,” wearing pajamas, sailor hats, and red, white, and blue outfits. Hemlocke Springs kicked things off at 8 PM with a short, high-energy set, backed by a drummer and keyboardist. She had the arena moving, and by the end of her half-hour, the crowd was more than ready for Conan.
At 9 PM, Olivia Rodrigo’s Bad Idea Right? blasted through the speakers. The second Olivia sang “I know I should stop,”the lights cut out and the arena erupted. Moments later, Conan Gray appeared, riding a bicycle onto a stage decorated with grass, a windmill, and a mailbox labeled “Pittsburgh, PA 9/16/25.” He slipped letters into the mailbox and pulled his microphone from it to start the night.
One of the most personal moments of the night came when Conan spotted Sandy at the barricade. Sandy, a grandmother who went viral on TikTok after her granddaughter surprised her with tickets (TikTok), was there with her daughter and granddaughter. The three generations helped Conan snap a wishbone, and Sandy’s pick led to Alley Rose. During the song, he sang directly to her with the line, “Where did you go, Sandy Rose?”
That fan connection carried into Vodka Cranberry, when Conan led his TikTok chant (Conan Gray TikTok). He sang “then I will, “and the crowd roared back, “don’t make me do this to you.” The exchange grew louder each time, filling the entire arena.
Throughout the 90-minute set, Conan mixed Wishbone songs with older favorites. He had several outfit changes, but these are the three main outfits:
- Opening look: a sailor outfit with a navy top, wide-leg pants, and a matching hat trimmed with a red scarf.
- Mid-show: before starting Romeo, he changed into a flowy white ruffled blouse with dramatic sleeves and high-waisted pants.
- Finale: a navy blue sparkly sailor suit detailed with gold buttons, chains, medals, and silver fringe on the shoulders.
He closed with Memories from Superache and Caramel from Wishbone. Even though the album had only been out a few weeks, fans screamed every lyric like they’d known the songs forever.
For Pittsburgh, it wasn’t just another stop on tour. Conan made it feel personal, with the outfits, the props, and the small moments he shared with fans. If you weren’t there, you missed the chance to be part of Pittsburgh’s own chapter of The Story.
Madison Hill is a photojournalist for our publication, see more of her work here.
