Conan Gray sings with the crowd during the Chicago leg of his "Superache" tour. Gray gave an electric and exciting performance, bringing themes of love and heartbreak onto the main stage. Photos by Lianna Amoruso / North by Northwestern

Surrounded by electric energy, we waited for the Chicago leg of Conan Gray’s Superache Tour to start. We quickly realized that being a fan of Conan is synonymous with being a Swiftie, as Taylor Swift classics blared over the loudspeakers and thousands of fans sang along. Most people wore merch from the Superache album, with some die-hard fans wearing merch from Conan’s first album or even his EP.

The enormous venue, flanked by towering bleacher-seats, loomed behind us in the pit; and even though I expected it, I was surprised at the sea of people waiting behind me to get a glimpse of the rising star.

Conan Gray is a 23-year-old YouTuber turned musician and UCLA-dropout, popular among Gen Z for his songs “Heather,” “Maniac” and more from his first pop album Kid Krow. One of his biggest influences is Taylor Swift, who inspires him due to her lyricism, poise and because she is badass, Gray has said.

The opener, Kacy Hill, had a calm and ethereal vibe that was very similar to Gray’s, but her lilting voice and bassbeat-heavy techno tracks didn’t satisfy my group’s hunger for teenage-angst heartbreak pop. We were embarrassed for the artist as the crowd was mostly silent, sometimes cheering when they were on the jumbotrons. Other fans held up their phones with text reading “clap” or “cheer” in an effort to engage attendees, but overall everyone eagerly awaited Gray’s entrance.

After Hill left the stage, fans began chanting Gray’s name. When he finally took the stage nearly an hour after the opener, he emerged from behind two white curtains, adorned by spotlights and backlighting from a heart-shaped screen. He wore a red matching set of flare pants and a vest with gold accents, complete with matching platform gold boots, his signature curls bouncing as he ran around the stage. I could barely hear him singing his hit song “Disaster” over the deafening cheers of his fans.

The show begins!

Superache is the quintessential Conan Gray album, building off the themes of heartbreak, unrequited love and emotional trauma of Kid Krow. It highlights his troubled past relationships in all spheres through songs like “Family Line,” “Yours” and “Memories,” emphasizing the pain he has gone through in the last few years. Gray is known for being extremely real in his work, making him one of the most listened to artists on Spotify– he is ranked 176 in the world and has over 20 million listeners monthly.

While his album’s themes are a bit depressing, Gray kept an energy about the crowd and commanded the stage, engaging with fans crowding the barricade. One of my favorite parts of hearing his songs live is that he actually changed them: most of the saddest songs were given new life, through more musicality or deeper bass and more fills by the musicians. For example, his song “Memories” has an explosive chorus on the record, but in the concert, it was like he took the song and put it on steroids. Gray also took numerous vocal risks, belting far higher notes and ad libbing more than he does in his records.

Despite this being his first ever sold-out show with over 8,000 fans, I felt very connected to Gray and the other fans around me. At one point in the show, Gray jokingly tried to deepen relationships between fans. For context, many of his songs are about a friend he was in love with that didn’t love him back, and that he never told about his affection. He joked that he wanted to fix that problem for us when he said, “are there any best friends here tonight…give them a hug…or even a kiss…on the mouth?!” The entire crowd screamed in glee as he subtly referenced his song “Heather.” During a more tender moment, he explained that his song “Family Line,” is about his troubled past and shaky family bonds. He asserted that, “You are not your family” and that your past experiences don’t define who you are. Cliché, but important advice that goes to show his maturity.

"You are not your family."

After the last song, the crowd once again chanted Gray’s name, basically begging for an encore. He obliged, and came bounding back onto the stage singing “Memories” which is a song about wishing a past love could just stay in memory, and not be someone you see day-to-day. I could not stop listening to that song for weeks after the concert. The entire crowd sang for their lives and Gray sang louder, and with more emotion, than he had the entire night; which is saying a lot about his ability to perform considering this was his last song of an entire album of heartbreak.

I nearly cried at the end of the cathartic performance, as these songs meant so much to us. Even though I had already heard almost every song he performed, they took on new life when they were live – something about each chord rumbling through my bones with the loudness of the speakers made each emotion he sang about more passionate and full. This concert was definitely worth the wait, and I think this was the perfect time to see him: while tickets are affordable! I would highly recommend seeing him before his Superache tour ends early next year.