He isn’t a mystery, but he isn’t just magic. Jackson Wang is talented, generous and perhaps a little bit tragic.

Wang brought his globe-trotting Magic Man tour to Chicago’s Wintrust Arena on May 4. Opening the show with “100 Ways” set the tone for the first half of the show with a romantic melancholy. While it made for a bit of a slow start to the show, Wang performed them with a deep sincerity and that soaring, soulful voice of his. Magic Man really kicked off the moment he asked the audience’s consent to make the show a little hotter. Songs from his Magic Man album like “Champagne Cool” and “Drive It Like You Stole It” kept fans on their feet with their funky grooves and Wang’s unabashed confidence.

Without much exaggeration, Wang is a true chameleon. For songs like “Cruel” and his latest single “Cheetah,” he prowled across the stage with his impressive crew of backup dancers. For “LMLY,” he recreates the set from the music video so he can cavort amongst his crew as they perform happy couples completely ignorant of his pining. A motif that admittedly felt a little overused was the magic elevator, which rose and fell as each section of the show began and ended. While a creative idea that goes perfectly with the tone and title of the tour, watching the transitional object eventually got repetitive. The part that made it feel more natural was Wang himself, who believed every step he took and every word he said in way that could be felt from the third row.

In fact, the show was almost uncomfortably personal at points. Wang gave lengthy speeches about the purpose of the show and the hardships he’s endured during his time as an entertainer, but the songs tonally clashed with these speeches often. Many of them were about lost love, including the excellent “LMLY” and “Blue,” which That being said, when the show transitioned into the more overtly sexy numbers, it did make for a jarring experience at times, especially when Wang decided to bring out an entire bottle of Hennessy.

These aren’t the actions a man takes when everything’s alright. While he did share the whiskey with his bandmates, it was clear throughout the show who the majority of the bottle went to. It’s a total rock star move, but it’s more than slightly concerning within the context of Wang’s speeches expressing a growing distaste for the industry he spent so much of his life in and the sense of a deep, gutteral loneliness one can only experience in that position. Even more indicative of this are the literal mascara tears he painted down his cheeks: it’s one part circus, one part sadness. It’s brilliant and heartbreaking in the same breath.

The moments Wang brought fans onstage with him weren’t just highlights for those lucky chosen two. During “The Moment” and “Dead,” a young woman with pigtails and a fishnet crop top Wang chose fully understood the assignment. While she did visibly fawn over Wang like any fan in that audience would have, she took her moment by the hair by dropping it like it’s hot and actively playing along with and into the fanservice. What happened when they entered the magic elevator doors closed and it filled with smoke? That’s between her and Wang.

The encore was easily the best part of the entire night – rather than come back to perform more songs, he simply came out dancing to remixes of “Blow” and “100 Ways” while bringing more and more people onstage with him. It was here Jackson seemed well and truly happy to be there: comfortable clothes, no makeup and his signature black beanie made him look less like a sex demon and more like just a regular dude who just wants to party. It’s clear he’s spent a great deal of his life being who he needs to be, as a common thread of the show was his journey to become who he wants to be. Let’s just hope he’s taking care of himself as he goes along that journey.

Jackson Wang is a consummate entertainer with an eye for detail and a deep admiration for his fans. Whether he’s aware of it or not, he’s already made them incredibly proud. Let’s hope, one day, he’ll see that for and within himself.

The North American leg of Jackson Wang’s Magic Man tour wrapped up on May 11 in New York, New York. The tour’s final stop will take place in Mexico City’s CDMX Arena on May 25.