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Jeremy Messersmith makes his Toronto debut at the Drake Hotel

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Jeremy Messersmith

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In the ‘60s, the original hipster—the hippie—was born. The original hipster’s music was emotional and spoke about real issues that united a whole generation, but ultimately simmered down and was replaced with other genres.

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Until the 2010s.

Jeremey Messersmith, playing at Toronto’s Drake Hotel on Feb. 11, 2014, is the latest in a long line of indie singers trying to make a unique mark on the music world.

Unfortunately, it wasn’t as memorable as he might have hoped.

Looking like a vague physical copy of Buddy Holly, Messersmith, clad in all black and wearing plastic glasses, did bring semi-entertaining music but was lacking in the repartee department. The crowd at the Drake couldn’t be called full by any stretch of the imagination, with those in attendance showing the same kind of reticence as teens at a high school dance: there seemed to be an invisible line drawn halfway in the room with a force field that prevented people from getting close to the stage.

Messersmith joked about the quietness and distance of the crowd a few times, but it only served to draw attention to sparse attendance, and he would have been better served to coax them nearer. It’s a hipster quality to speak as though you don’t care about things like attention and audience, but even Bob Dylan would have admitted that his career wouldn’t have gone anywhere had crowds like Messersmith’s consistently showed up.

It was almost painful watching him josh with the audience about their meagreness, even when it was disguised with wit. “I don’t want a riot on my hands,” Messersmith said in response to asking the crowd what songs they wanted to hear, but lamenting a second later, “Oh, I wish I had a riot on my hands.”

Musically speaking, his set was fairly tight as the band transitioned smoothly from one song to another. Thankfully, he didn’t spend a lot of time ruing the library atmosphere and instead focused on the music that’s made him a small draw in Toronto.

There were a couple of hiccups—with Messersmith the weakest instrumentally—but his band is composed of solid musicians who know it’s best to stay on track and not try to reinvent the wheel.

From a quick search on the internet, Messersmith appears to be a big-deal-in-the-making in his native United States, but loses something in transition up north. For whatever reason, his blasé hipster attitude tends to divide crowds rather than speak to him, and he would be well-served to address the different climates if he wants to successfully break into Canada.

It’s not that Torontonians—or Canadians in general—are a snobby, hard-to-please bunch, but that they’re a little more reserved than their American counterparts and need a bit more encouragement to come out of their shells.

But until that happens, his potential remains untapped.

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