Conan Gray's journey has come full circle — and it all led him back to Madison Square Garden. Speaking live from the Mercedes-Benz Interview Lounge backstage at this year's iHeartRadio Z100 Jingle Ball presented by Capital One, the singer-songwriter reflected on how surreal it feels to now be performing at the very event where he once stood in the crowd as a fan.

Just a few years ago, Conan was "barricade watching Olivia Rodrigo" at Jingle Ball. Now, he’s stepping onto the same stage himself. “It’s exciting,” he said, soaking in the moment. “I feel like this whole event is just very ... everyone’s very happy. And Jingle Ball has had so many special performers over the years, so I feel very lucky.”

That sense of gratitude followed him throughout the conversation, especially as he talked about the camaraderie backstage. Jingle Ball, for Conan, feels less like a high-pressure industry event and more like a reunion. “I love Audrey Hobert,” he shared, adding that seeing friends like Laufey on the lineup has turned the tour into “a nice little friend group affair… a nice excuse to see each other.”

As a songwriter known for emotional honesty, Conan didn’t shy away from discussing the less glamorous parts of the creative process—namely, writer’s block. In classic Conan fashion, he explained it with a vivid metaphor. “Sometimes you just gotta pee out the kidney stone,” he joked. “It’s painful. You just like — even if you’re making crap — just keep trying, ’cause you never know something beautiful, a kidney stone might come out.” Crude imagery aside, the message was clear: persistence is everything.

That raw, no-expectations mindset played a huge role in Wishbone, the album he released over the summer. Conan described it as his most personal work yet. “Every guard that I’ve ever had is down,” he said. “There was no expectation for it. I wrote it at a time where no one was thinking that I was going to make an album… and it ended up just being this passion project for me.” He added proudly, “It’s really just unbelievably me.”

Performing that music at Madison Square Garden only amplifies the emotion. Despite having played the venue before, Conan admitted the magic hasn’t worn off. “I definitely was holding back tears the first time I walked out and I was supposed to sing my first note,” he said. “There’s just something about it. When you’re a kid, you hear New York City and you think Madison Square Garden—that’s your only concept of what this city even is.”

From barricade fan to Jingle Ball performer, Conan Gray’s story is a reminder that dreams can sneak up on you when you’re busy being yourself — and sometimes, standing on the world’s most iconic stage, it all finally sinks in.

To relive the holiday magic, iHeartRadio is partnering with ABC to bring the iHeartRadio Jingle Ball Tour to even more fans across the country, as an exclusive network special will be aired on December 17th and next day on Hulu.