Great Sketches #1: “Progression of a Mad Hatter” by Derrick Comedy

I like comedy. Do you like comedy? Not everyone does. But as someone who appreciates short stories, comic ideas and sharing YouTube videos, I’ve decided to do a series about the 50 sketches I consider among the best I’ve ever witnessed. These won’t be ranked and won’t come in any particular order, but since I’m trying to encapsulate a whole range of different styles and performers, chances are something you like will pop up on this list eventually. We begin today with a 2006 sketch from Derrick Comedy, the group that gave us the erstwhile Childish Gambino and Troy from Community, Donald Glover.

Derrick has more famous sketches, but this is the one that sticks with me the most. It’s very old-fashioned in its approach and feels almost like a vaudeville bit as filmed in someone’s living room on a home video camera. The same year this sketch appeared, the 23-year-old Glover would get hired as a writer for 30 Rock, setting the course for his future superstardom, and I can imagine him using this, at least in the early days, as a kind of sizzle real for everything he can do in a single clip.

The premise here is very simple. Donald Glover plays a modern day hatmaker who decides to practice his craft “the old fashioned way”, even though we’re told that this has led to previous hatters losing their sanity. It’s all really just a way to play out someone’s slow escape from reality, and what makes it is Glover’s commitment to what he’s doing as his actions gradually get more absurd.

Each ridiculous thing he says is delivered with a completely straight face, as if he’s speaking a different language (the line “slimy. What’s for dessert?” has shades of Tracy Morgan). Even when he’s dancing around in his underwear to Stevie Wonder, there’s never a sense that Glover’s playing up his silliness just for the camera. In a weird way, it’s almost tragic, pivoting to the same kind of poignancy as a zillion “right to life” dramas in the span of a second. And as far as comedy writing goes, it’s hard to argue that there’s ever been a more finely-crafted sentence than “I need you and the kids to get in this orange: I’m going to go build a lamppost out of cinnamon buns” in American history. The ability to get utterly caught up in your character, even for a goofy internet video, is a great tool for comedian and it’s clearly served Glover well.

Yes, you do have to get past the poor production values, which sometimes make the dialogue hard to hear. It’s also a pretty limited sketch: all of the comedy comes from one character, and the hatter’s wife (I can’t find the actor’s name, though it appears to be Melanie) is a traditional “straight” role, who only really exists to drive the plot forward. Still, she does an excellent job playing it like a drama, especially in the final scene, which couldn’t have been easy given everything leading up to it.

I remember an interview with Glover in which he said that the first Derrick sketches that appeared on YouTube in the early days were met with confusion, as if people didn’t yet understand that the platform wasn’t just for home movies. Derrick was certainly one of the first groups to take advantage of this and bits like this are still around to show us why.

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