Taylor Bennett sings “2 Much” at his Summerfest performance

In some respects, Taylor Bennett is not in a good position.

If you google his name, he’s simply described as “Chance The Rapper’s brother,” which is true, but isn’t really fair to an up-and-coming artist looking to make a name for himself. So when he took the spotlight at Miller Lite Oasis or another stage at 6:30 on Friday night, he was understandably under pressure to live up to his brother’s fame. It’s little brother syndrome in every sense of the word, albeit on a grander scale considering the size of Chance The Rapper at his peak.

That “little brother” syndrome, however, showed up at Friday’s performance, which was chaotic from the start. At 6:30 a.m., a Taylor Bennett Entertainment logo appeared on the LED screens backstage while Milwaukee DJ Nic Stokes was pumping up the crowd. His band, consisting of a drummer, DJ and bassist, started line-checking Stokes’ set, which is fine in short bursts. Then it continued until an audio cluster that gave you the impression that something was really wrong. Bennett took the stage at 7:10 a.m., unfazed.

Once he got on stage, he was all in, trying his best to pump up the crowd during his performance, repeatedly urging “Wisconsin” to put his hands up as if he didn’t live just 90 minutes south of Milwaukee. Still, his flow was perfect, delivering a wealth of lyrics for “Roof Gone” and “Dancing In The Rain,” and delivering complicated verses with ease. As an intro to the latter track, he blamed the rain for his tardiness… only it hadn’t rained at that point on Friday. It was a swing, but a miss.

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It’s fitting that Bennett’s latest single is titled ‘2 Much’ because, frankly, that was his approach to his performance too. Bennett certainly tried hard, but at Oasis he didn’t seem to have it quite working. Over the course of 45 minutes, he used pretty much every crowd-pleasing trick he could find to get the crowd going. A few background dancers came on stage behind him for select songs, and mid-set, he took off his shirt to get a few cheers from the crowd. He asked for phones and lighters in the sky, which didn’t work either because it was still light outside. Through no real fault of his own, the show didn’t go down well with the crowd that had gathered to see him.

With the schedule shifted, Bennett’s set segued right into rapper Gloss Up’s performance, which was scheduled for 8 p.m. at Oasis. Bennett attempted an encore of sorts, though, and that’s when things finally came alive. He said his time was up, but he had a crew from Chicago with him, so he had to do his last song. A quick medley of Chicago tracks, including a bold decision to play Kanye West’s “Father Stretch My Hands Pt. 1,” got the crowd cheering. That led to the footwork-ready “Chi-Town Anthem” to close things out. It was a sign of life from a show that was dogged by bad luck from the start but always had plenty of potential.

In some ways, Taylor Bennett is forced to ride his brother’s wave. The two look a lot alike, sound alike vocally, and have similar music stylistically. However, Chance’s reputation has declined in recent years, and Taylor may have to bear that burden as well. On Friday night, he tried hard to carve out his own personality on all of the above fronts, but the pieces never really fit together.