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In some respects, Taylor Bennett has the cards stacked against him.
When you Google his name, he’s described as simply “Chance The Rapper’s brother,” which, while true, isn’t really fair to an up-and-coming artist looking to make a name for himself. So when it was his turn to take the spotlight on Friday evening for a 6:30 p.m. slot at the Miller Lite Oasis, or any stage, there was understandable pressure for him to live up to his brother’s accolades. It is quite literally little brother syndrome, albeit on a grander scale given the magnitude of Chance The Rapper at his peak.
However, that little brother syndrome manifested itself in Friday’s performance, which was in disarray from the jump. At 6:30, a logo for Taylor Bennett Entertainment appeared on the LED screens behind the stage, as Milwaukee’s DJ Nic Stokes warmed up the crowd. His band, comprised of a drummer, DJ., and bass player, began line checking over Stokes’ set, which is fine in short bursts. Then it would continue to the point of an audio cluster that would give you the impression something was really off. Bennett would hit the stage at 7:10, unphased.
When he did get to the stage, he was locked in, trying to do his best to hype the crowd up during his set. He kept urging “Wisconsin” to get their hands up, as if he didn’t live just 90 minutes south of Milwaukee. That being said, his flow was on point, bringing a plethora of lyrics to “Roof Gone” and “Dancing In The Rain” and performing intricate verses with ease. To intro the latter track, he would blame his tardiness on the rain… except it hadn’t rained at that point on Friday. It was a swing, but a miss.
It’s fitting that Bennett’s most recent single is titled “2 Much,” because frankly, that was his approach to his performance. There was certainly effort on Bennett’s behalf, but things didn’t really seem to click for him at the Oasis. In the course of 45 minutes, he utilized just about every audience-invoking gimmick that he could to try and get the crowd going. A pair of backup dancers hit the stage behind him for select songs, and he’d take his shirt off midway through the set to try and elicit some cheers from the crowd. He’d ask for phones and lighters up in the sky, which also fell flat, because it was still light out. Through no real fault of his own, the show failed to resonate with a crowd that formed to see him.
Being that the schedule was pushed back, Bennett’s set flowed right into rapper Gloss Up, who was slated for the 8 p.m. set time at the Oasis. Bennett attempted an encore of sorts, though, which is when things finally came to life. He stated that his time was up, but he had a crew from Chicago with him, so he needed to do his finale. A quick medley of Chicago tracks, including a bold choice in playing Kanye West’s “Father Stretch My Hands Pt. 1,” got the crowd up. That led into the footwork-ready “Chi-Town Anthem” to close things out. It was a sign of life from a show that was snakebit from the start, but always had plenty of potential.
In some respects, Taylor Bennett is forced to ride the wave of his brother. The two look very similar, vocally sound like one another, and from a style standpoint, have similar sounding music. That being said, Chance’s stock has fallen in recent years, and Taylor may also have to bear that weight as well. On Friday night, he gave a good effort to try and distinguish his own persona on all of the aforementioned fronts, but the pieces never really came together for him.
