The Stealthy Confidence of Jacob Williams

Matt Craig
3 min readApr 3, 2017

A comedian who’s great by convincing you he sucks

One thing that has always fascinated me is the art of stand-up comedy. The concept that one person talking, usually about nothing in particular, could be so valuable as to attract a crowd of people to come watch it is incredible. And while I appreciate the structure, the rhythms, and the vocabulary required to produce laughter from a crowd, what really impresses me is the risk involved. The comedian cannot know whether or not a joke is going to land until he tells it, so in a sense he is stepping blindly off a cliff hoping to be caught by laughs, over and over again.

I hadn’t planned on going to see Jacob Williams on Wednesday until that afternoon, when I received an email detailing who he was and when the show was. I had frankly never heard of him, hadn’t seen him on America’s Got Talent, and had only a very minor knowledge of the show he was on, “Wild n’ Out.” But my interest in stand-up compelled me, and I decided to attend.

I grabbed a picture with Williams after the show. Point at the guy who does worse with the ladies!

First impressions are important everywhere, but in stand-up they are absolutely vital. When Gabriel Iglesias walks out on the stage, the audience can expect jokes about his weight. If you see Dave Chappelle you know you’ll hear racial jokes.

The comedian essentially plays a character of himself, and for lesser-known performers it’s often beneficial for his or her “shtick” to be easily identifiable. It’s something that Williams does exceptionally well.

His dress was normal, jeans and a t-shirt, but his glasses and haircut immediately call to mind any number of dorks or nerds you’ve inevitably seen on television or in movies. Even the way he walked to the microphone screamed, “I AM NOT THREATENING IN ANY WAY,” emphasized by his slumped shoulders and the way he went on to hold the microphone as if he could barely keep it up.

The whole set was a tirade of self-abuse, taking charming self-deprecation to its absurd extreme. “My dream date would be going on one” was one of his milder lines. Instead of segues, Williams would simply pause for a moment and say, “so there’s that” before going to his next bit. Topics included his lack of friends, his lack of romantic relationships, and even his lack of career success. The act even ended with a grand finale of, “so, uh does anyone have any questions?”

That isn’t to say he wasn’t funny, as I found myself laughing for the entire hour. The way that he was able to set the audience up with his storytelling and then deliver a surprising, expectation-shattering punch line was top notch. And he navigated the waters between “clean” comedy and comedy for adults excellently.

One of the questions at the end was, in fact, whether or not he was this awkward in real life. His reply was that he was. But the primary question that came to my mind was how one could be so obviously self-conscious, riddled with self-doubt, and still perform stand-up comedy? If the stories he was telling about himself were true, how could he put himself out on that ledge and have the courage to step off?

I imagine myself standing in front of a crowd trying to get them to laugh, telling a story about the funniest day of my life. That is scary enough. But to share stories of embarrassment? What if the audience doesn’t find them funny? Then is it just sad?

That’s the territory Jacob Williams thrives in, and I applaud him for it. For a guy who talks about not having the courage to approach women, and makes a living telling jokes about people not coming to his birthday party, he certainly has the confidence necessary to become a great comedian.

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