How Colin Quinn Became Comedy’s Coolest History Teacher

When considering Colin Quinn’s place in history, he can’t help but seem – at least at first glance – like something of a tragic figure. There are two aspects of his career that every comedy nerd knows: his short-lived run as the anchor of Weekend Update and his even more short-lived run as the host of the cult classic series Tough Crowd. In each of those scenarios, it feels like he wasn’t really given a fair shot.

When he took over Update after the unceremonious firing of Norm MacDonald, he had the unenviable task of succeeding one of the most beloved anchors in the history of the segment. He poked at fun at the situation in his first Update, but he could never outrun the narrative. He was relieved of his duties after the 1999-2000 season, replaced by the more commercially viable tandem of Jimmy Fallon and Tina Fey. Three years later, on Tough Crowd, he hosted a show that involved intense debate between fellow comics, including regulars like Jim Norton, Greg Giraldo, Nick DiPaolo, and Patrice O’Neal. The show had its share of devoted fans, but never captured a mainstream audience, and it was canceled in 2004 and replaced with the more successful Colbert Report a year later. But while Quinn’s fate in these scenarios was unfortunate, anyone who views his career as a disappointment hasn’t been paying attention. In the 2010s, Quinn has re-invented himself with a new persona: comedy’s greatest historian.

Quinn’s latest Netflix special, The New York Story, debuted on the platform last month. In it, he gives an extremely thorough retelling of how the city of New York came to be, exploring everything from why the city wasn’t called New London, to the exact order that each group of immigrants came to the country and how they interacted with each other. Even for someone often known as a quintessential New York comic (at least partially due to his thick accent), it’s a stunningly comprehensive work, as he crams every bit of information he possibly can about New York’s history into the span of hour. This special would be surprising were it not the fact that he had already done similar projects twice before.

In 2011, he released the HBO special Long Story Short, which covered all of history from the prehistoric era to modern times. Two years later, he followed that up with Unconstitutional, which took a deep dive into the history of how the constitution was created, as well as the overall effect it had on the development of America. As we can see, Quinn has no problem taking a large, broad topic and exploring it in the most comprehensive way possible. What allows him to succeed at this is his stunning abilities as a storyteller. Anyone who has followed Quinn throughout his career knows that he has quite a knack for going into great detail with his stories, describing minutiae that seems unimportant at first but ends up being essential. He knows exactly what parts of the story to tell and what to leave out, and the tales he tells in his specials have been enthralling as a result.

While his transformation into comedy’s coolest 8th grade social studies teacher might be a bit surprising for someone who best remembers him from Update and Tough Crowd, it’s really not much of a departure, as he largely maintains the persona that defined him in his early years. Quinn is what you might call a rough-around-the-edges comic, as he often divulges into stereotypical humor that might catch the ire of the more culturally sensitive crowd. But what sets Quinn apart from many other comics who seek to challenge the so-called PC police is that he’s actually capable of justifying his decision to Go There. In The New York Story, several of his jokes play on ethnic stereotypes, and honestly, they would have fallen flat in the hands of any number of lesser comics. But what makes it work is that Quinn doesn’t make these jokes just for the sake of making them; rather, he has a larger point. Specifically, he discusses how New York’s various cultures and ethnicities actually interact less with each other now than they did 40 years ago, and perhaps the recent trend of being afraid to say anything potentially hurtful has (perhaps unintentionally) contributed to that divide. Admittedly, an argument like this will always seem spurious when coming from a white guy, but out of all the comics who trade in stereotypes, Colin Quinn is one of the rare few who actually has a greater purpose for it.

Quinn’s staying power is nothing short of admirable. After failing to find anything more than a cult audience on SNL and Tough Crowd, Quinn easily could have shrunk from the moment, and been known to history merely as “the guy who did Update after Norm and before Jimmy and Tina” and “the guy who was on after Jon Stewart before Colbert was.” Instead, he’s become so much more than that. His last three standup specials have proven that he is one of comedy’s most adept storytellers as well as its most thorough historian. He may never have become a mainstream comedian, but at this point it doesn’t matter – he’s firmly established himself as one of the most important (and underrated) comics of our time.

How Colin Quinn Became Comedy’s Coolest History Teacher