
Yesterday I set out to illuminate Homer’s paintings using a silly font-selecting method: Pick the free fonts based primarily on their name alone.
What was my motivation? One of my friends asked, “I am curious why you underwent this exercise Matt”.
I asked myself the same question as I was doing this. A handful reasons why I did this (in no particular order):
The process
A serious of events led up to this. After writing the post about Winslow Homer’s dichotomies, I created the feature image as a collage of the 8 paintings.

The collage was kinda nice, but it doesn’t really illustrate the point of the dichotomies.
Since the dichotomies for each painting can be distilled down to just two words, I thought it might look interesting if each painting had the words plastered really big on each painting.
Since I was putting the text onto each painting, I needed a font to use. I could have used some bold or heavy font. Or I could have spent a lot of time trying to finesse and pick just the right font, but since these are descriptive words, there’s gotta be a font named after each word. Like, a font named Life, a font named Death, etc.
That would be my font selection method. Just pick the font based primarily on the font name.
Playing with the world of free fonts
The world of fonts is a fascinating world. There are SOOOOO many fonts out there, the volume is mind-blowing. When I learned design in the mid 90s, font availability was really limited. So limited that my design teacher got a CD-ROM of fonts that had ripoff names. Our ripoff version of Bodoni was named “Bodoxi”! Clearface was named “Clerface”.
To now live in a world with hundreds of thousands of font makes me want to delve into the options more. Five years ago I made a webcomic where I analyzed the absolute bottom of the barrel fonts from each website. I love those long tail fonts. It’s like searching for something in Spotify, and going into the long tail results. Those homemade songs that so so crappy, they are endearing.
When searching on font sites for specific descriptive words like “life” and “death”, I thought most of the results would be really bad fonts. But the results were pleasantly surprising. The fonts were actually pretty good! At least, for the purpose that I was using them—as single words plastered on an image.
Of course, most of these fonts wouldn’t be used as body text. The majority are decorative fonts. And for that purpose, they work pretty well!
Having fun with design
I don’t get to just straight-up design fun things like this for work. Since I work as the only designer in an in-house department, most of my work is within a particular style. It was refreshing to just have fun.
Along the way, this started to feel a little bit like a Design 101 assignment. As an experienced designer, that feeling turned me off a bit. But whatever, I just wanted to have fun with it.
No filter for unfocused work
Oftentimes my brain will think of something, and I’ll simply do it. I don’t have much of a filter to say “Oh this is stupid, don’t do it.” I have no filter that says, “this is not within the focus of what I want to do with my career.”
It indeed can be a fault of mine to not have this focus. But it can also be a strength. I enjoy being open-minded and exploring. This approach is heavily influenced by my Montessori upbringing. I went to Montessori pre-school/kindergarten, and my mom was a Montessori teacher (with a degree in psychology).
Sports look
Since I was plastering the text really big over the images, it started to feel like some of the designs that you’ll see in sports promos. I briefly looked at some sports designs on Behance for inspiration. I didn’t really carry any ideas forward, I just looked at Behance to be energized. At some point I’d like to look back at the sports designs and lift some of their tricks.
As a designer, it’s always good to be adding more tricks to your repertoire.
Plus, it’s just fun to think of designing a Winslow Homer painting to look like a modern sports promotion. That sort of approach is really intriguing to me. I might be exploring it with more open domain artwork.
Art Institute of Chicago obsession
I’ve written over 50 posts about the Art Institute Chicago on a variety of topics such as:
- Making art in the museum (Matching baseball cards with artwork, folding Felix Gonzalez-Torres’ artwork into origami)
- Observing the art in new ways (through a kaleidoscope lens or printed on toilet paper
- Their collection: (compared to Star Wars, analyzing their 11 napkins)
- Reviews of their shows (El Greco, Warhol, Picasso)
For a while in 2016, the Twitter account that @artinstitutechi replied to the most was @spudart.

I should gather up a collection of all the times they replied and retweeted me. It was a fun run. In 2018, @artinstitutechi gave me a very nice reply:
I just absolutely love playing around with their collection.
Winslow Homer
In college, our sculpture professor compared one of my artworks with Winslow Homer. It’s such a silly thing, but when your work is compared to someone famous, there’s this sort of newborn fascination for that artist. Like, you have a connection somehow with the artist. I still feel that way with Homer.
In my case, the connection was EXTREMELY thin. Here’s the artwork from 1997:

I called it “Twister Turner”—a play on the artist Joseph Mallord William Turner, the 19th Century English painter who would often depict dramatic storm scenes.
I painted a quick watercolor of a sky, framed it with some construction horse wood. In front of the watercolor is a long vertical bolt that connects the bottom part of the frame with the top. The viewer is invited to twist the nut on the bolt. You could make the nut go really low or make it really high. Or spin it to the middle.
I called it “Twisted Turner”
1) Twister: nut and screw (the nut twists around).
2) Twister: landscape with dramatic weather conditions implies a tornado is nearby. The construction horse wood frame implies the damage done by a twister.
3) Twisted: The watercolors call to mind the artist Joseph Mallord William Turner.
Ok, that was a little tangent. The point being: even though artwork is a twist on the Turner the artist, it still got compared to Winslow Homer. That stuck with me.
Human touch with free internet fonts
Every font is designed by a person. That may be obvious, but give it some thought for a moment. We often pick fonts from a menu, and simply apply it to our text. Done deal. We focus on the font and what it can do.
When I’m looking for a font, I’ll head to dafont.com and download 20-30 fonts without blinking an eye. Total mass product. Lots of fonts. They almost become anonymous. Just a bulk list. Then I try each font. Debating which one fits my purpose the best.
Once I select the font, sometimes I’ll head back to dafont.com to see who the designer is. I really enjoy seeing the humanity behind the fonts. For instance, in the Relaxed/Resigned image, I used the font named “Relax”

According to dafont.com, the “Relax” font is designed by a user named “put out into the deep“. In addition to “Relax”, she has designed 10 fonts.
Her dafont.com profile lists her website as calej.blogspot.com. From her blog, you can see that she is Catholic and blogs regularly. One of her recent posts is about resources for Lent. She also sings on soundcloud.com. I like her Psalm 98 track.
(Which is an interesting connect for me, because last year I was hand-writing Psalm 100 once a day).
She’s written about her font “Relax”, saying, “The Relax font is in a calligraphy script style that is playful and decidedly cheery.” I’ll definitely have to do a rendition of Psalm 100 in her font.
So fascinating! All this from discovering her font on dafont.com. The “Relax” font now has become alive and taken on so many new dimensions.