Upstatement Talks with Typographer Cyrus Highsmith

Will Millar
Upstatement
Published in
4 min readFeb 25, 2019

Cyrus Highsmith is a designer, illustrator, author, and teacher based in Providence, Rhode Island. After working at Font Bureau, he started Occupant Fonts in 2016. He teaches typography at RISD and is the author of Inside Paragraphs: Typographic Fundamentals, which he describes as an educational comic book.

Cyrus has designed typefaces for The Wall Street Journal, Ford Motor Company, and ESPN. He recently came to Upstatement to give a talk about his work, and we had a chance to ask him some questions.

Allium from Occupant Fonts

Your work combines design, writing, teaching, and illustration. How do all these things fit together for you?

I do the things I’m interested in doing. I guess the thing that unites them at a very basic level is telling a story. Abstract drawing is like a conversation in your head, but a typeface is used to tell a story in the literal sense.

There’s a story that’s inside the type about how the layers get along and have a conversation because they have to work together. It becomes an argument if it becomes too loud, but if everyone is agreeing with each other too much, then all the letters look the same and you won’t be able to read it. So there’s a kind of dialogue between it all.

Inside Paragraphs: Typographic Fundamentals

What was hard about writing your book Inside Paragraphs?

I had never written a book before, so that took a long time. A lot of drafts — a lot of taking stuff out. My wife, Anna, was the editor and I realize now she should have been the co-author because she went over every single sentence in that book and helped me make it clear.

It was tricky because I’d write the text and then I’d try to do the drawing. If I realized if the drawing was hard to do, it meant that I hadn’t written clearly! So there was this kind of interesting back-and-forth between writing the thing and trying to draw it — or figuring out the drawing and realizing that’s not actually what I wrote.

Do you have a favorite letter? Or one that you start a typeface with?

When I’m sketching an idea I draw whatever letter I feel like. A lot of times we see the uppercase R because it has one of everything — one straight, one diagonal, and one round shape.

For me, lowercase tends to have more personality. I like the lowercase g. I notice in my sketchbooks I draw a lot of lowercase as. I think they have a lot of personality in the shapes. But when I really sit down to draw a typeface, I usually draw a lowercase n, a lowercase o, and a lowercase e. With those you can also start to figure out the spacing and things like that.

Contributors to the Letter G

How do you think about drawing as part of your practice?

I physically just like to draw. I keep a sketchbook and draw every day. In terms of type design, I like to draw shapes. I don’t tend to draw volume. I draw flat shapes, which has been influenced by drawing letters.

When you draw letters with vectors — you’re not drawing a line — you’re drawing an edge of a black shape and a white shape at the same time. If you think of a line as an edge between the shape of thing you’re drawing and the shape of the space — you’re drawing two things at once. When you think about the line that way and edges that way, then you can switch to thinking about shape.

“Tiny drawings for my daughter”

What do you think is essential about type design today?

When you focus on a very specific use, think about that in a deep way, and combine that with a seriousness about craft, then you end up with work that is imaginative and inventive and work that adds stuff to the typographic system.

Apple Bear Cat

Thanks to Cyrus for coming in for a great talk and for answering our questions! Thanks to Joseph Allegro for the Upstatement connection and help with the interview. Follow type design commentary from Cyrus and Occupant Fonts on Twitter, or check out more illustrations on his Tumblr.

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Will Millar
Upstatement

Designer at Upstatement and bathrobe evangelist