From ‘Sunset Season’ to ‘Wishbone’: Conan Gray Live in Philly

I started listening to Conan Gray when I was 14 years old. I found his 2018 EP Sunset Season randomly on Spotify and was immediately hooked. His songs felt like pages ripped straight out of a teenage diary, melodramatic, honest and somehow perfectly capturing every confusing emotion that came with growing up.

I first saw him live in 2022 at The Fillmore Philadelphia after he released his debut album Kid Krow, a truly no-skip album. My friends and I sat outside in the freezing cold for 10 hours waiting to get in, shivering but buzzing with excitement for a performance we knew would be unforgettable.

PHOTOS BY JACKILYN COOPER

Four years later, I found myself in a very different setting. This time it was in Xfinity Mobile Arena packed with thousands of fans for Gray’s largest headlining tour celebrating his fourth album, Wishbone. Somehow the night made me feel like that same middle school fan again, just with a few more years of lived experience, heartbreak and emotional damage under my belt. The music that once felt like dramatic teenage catharsis now felt more personal, like I had finally grown into the emotions behind the songs after experiencing my own share of messy relationships, heartbreak and the long process of discovering who I am.

The Wishbone era is rooted in visual storytelling, and that narrative was brought to life on stage. The concert unfolded in four acts, using the wishbone as a metaphor to explore heartbreak, yearning, bad luck in love and eventual growth.

The show opened with act one: “a wishbone never breaks even.” Gray came on stage riding a bicycle and wearing a sailor costume, dramatically delivering a letter into a mailbox labeled “Philadelphia.” It was quirky, theatrical and unmistakably Conan. Moments later the first notes of “My World” rang out and the energy in the arena exploded.

From the very beginning it was clear that everyone there knew every word. Fans screamed the lyrics like they had been waiting their entire lives for this moment. The arena felt electric, like thousands of people were suddenly sharing the exact same emotion.

It felt like everyone collectively agreed that the night would include dancing, crying, laughing and screaming every lyric at the top of our lungs.

And that’s exactly what we did.

He quickly launched into “Never Ending Song” from Found Heaven, a track filled with bright ’80s-inspired new wave energy. The momentum continued with fan favorites “Care” and “Wish You Were Sober.” The production was massive, with towering visuals, vibrant lighting and a full band, but Gray still managed to make the performance feel intimate, like he was singing directly to each person in the crowd.

The mood shifted during the second act, titled “I got the short end of the stick.” In a playful but vulnerable transition, Gray changed into sparkly periwinkle blue pajamas and flopped dramatically into a bed onstage, referencing the bedroom where much of the album was written.

This act leaned into some of his most emotionally raw songs and explored rejection, loneliness and self doubt through songs like “Class Clown” and “People Watching.”

“The Cut That Always Bleeds” and “Eleven Eleven” slowed everything down even further. Phones lit up the arena, turning the crowd into a sea of tiny glowing lights as thousands of voices softly sang along.

One of the most special moments of the night came during the acoustic “Conan’s Campfire” section, where Gray performs a surprise song each show. Nothing could have prepared me for the choice that night.

The opening notes of “Crush Culture” from Sunset Season began to play and the OG fans absolutely lost it.

This was a song I used to listen to religiously while doing homework in my childhood bedroom, so finally hearing it live eight years later felt surreal. It was like a tiny time capsule from my teenage years.

Act three, “I took the long way to realization” brought some surprises. “Romeo” was dramatic and theatrical, but the biggest moment came when Gray debuted an unreleased song titled “The Best,” performing it live for the very first time.

PHOTOS BY JACKILYN COOPER

Then came one of the most interactive traditions of the tour, the wishbone song pick; Each night Gray chooses a fan to break a wishbone with him. Whoever gets the bigger piece chooses between two songs.

Our fan representative was a girl dressed as a carrot, an iconic reference to Gray’s well-known love of carrot cake. When she won the bigger piece she chose “Sunset Tower,” a high-energy, upbeat track that was clearly meant to be performed live.

Then came “Heather.”

Gray grinned and said, “Heather, if you’re out there…I’m sorry. But I’m also not. Because this song is a banger.”

This song, which I repeatedly listened to during my sophomore and junior year of high school, has become Gray’s most recognizable hit thanks to its massive popularity on TikTok. This performance felt different though. He performed the extended version with the “lost verse,” first released on the five-year anniversary album Kid Krow, Decomposed. Hearing the entire arena scream those lyrics back at him felt almost cathartic.

“Family Line” and “Connell” brought the show into a quieter, more reflective space again without completely losing the energy. It felt emotional but comforting, like a collective deep breath before the final stretch.

By the fourth act, “I wished for love, and I found it,” the energy flipped again.

“Actor” and “Maniac” turned the arena into a full blown dance party. During the extended intro of “Maniac,” Gray introduced each member of the band while the crowd cheered wildly.

“Vodka Cranberry,” the lead single from Wishbone, closed the main set in a glittery rush of energy. The song’s message about reclaiming control after a messy relationship felt like the perfect triumphant ending.

As the band walked offstage, the lights dropped to black. The crowd immediately began chanting “Conan! Conan!” into the darkness, their voices filling the venue until the lights suddenly flickered back on for the encore.

Gray appeared back on stage in a glittery blue sailor outfit and began singing “Memories,” which felt softer, almost like a quiet conversation between him and the audience. “Caramel” wrapped up the night on a sweet and celebratory note. The upbeat song, about the bittersweet pull of a love you can’t quite quit, sent the crowd out on one last burst of energy.

What made this show stand out was not just the production or the theatrics — it was how natural everything felt. Even while performing in a massive arena, the show still felt intimate. He simply sang, let the crowd sing back and allowed the moment to exist.

By the end of the night everyone left smiling, exhausted and probably still belting lyrics at the top of their lungs on the way home.

At 27, the pop singer-songwriter has come a long way from his early days posting videos on YouTube. But somehow, even with arena lights, elaborate sets and thousands of screaming fans, Conan Gray still manages to make his music feel like it is meant for our younger selves listening alone in their bedrooms.

For those of us who have been listening since the early days, the night carried a quiet sense of nostalgia. For a few hours, singing along with thousands of other fans, I felt like that teenager again.

And judging by the crowd that night, I was not the only one.