Using a silly font-picking method to illuminate Winslow Homer

Croquet Flirt

Winslow Homer’s paintings are full of dichotomies. Earlier this week, I uncovered eight paintings in the Art Institute of Chicago’s collection with wonderful dual meanings. Themes like life and death captured in one painting.

To really punch these double interpretations, I had fun photoshopping two words onto each painting. Each word is really BIG—as in it bleeds off the edges of the painting. Adding to the flair, each word is set in a different font.

Which font should I use? I’m applying an unusual method for the font selection. If the word is “life”, then I search for a font named “Life” and use that font to style the “life” word. For the word “death”, I use a font named “Death“.

Yes, there are actually fonts with the name “Life”, and fonts named “Death”. Hundreds of thousands of fonts exist online on sites like and Font creators often name their fonts with fun or descriptive names.

Using this constraint, I’ll be finding fonts with the following names:

Some of these words may be challenging, but let’s see how it plays out. We might uncover some really BAD fonts, because there are plenty of silly fonts online.

An extra bonus is that there may be some really BAD fonts. I love bad fonts. I even made a webcomic where I used each of the absolute least popular font from each of the 8 biggest font websites.

Matching up 19th century masterpiece paintings with 21st century home-made fonts

Alert & Lost

Font for “Alert”
Five fonts exist with the word “alert”. This one has nice letter forms.
• Alert Covid by Khurasan

Font for “Lost”
• Lost Type by Xerographer Fonts

Image: Adirondacks Guide, 1892 (via CC0 Public Domain Designation)

Caption: “His gaze, forward and slightly elevated, is evocative; one senses that the old man is at once alert to nature and lost in his own contemplations.”

Nurtures & Deprives

Font for “Nurtures”
No font with the word “nurture” or “nurturing”, so instead I went with a font that has the word “care”
• Care Bear Family

Font for “Deprives”
This was a really tough painting. Both words didn’t have a font. For “deprives” I went with “bankrupt”.
• Bankruptcy by Chequered Ink

Image: The Herring Net, 1885 (via CC0 Public Domain Designation)

Caption: “While one fisherman hauls in the netted and glistening herring, the other unloads the catch. Utilizing the teamwork so necessary for survival, both strive to steady the precarious boat as it rides the incoming swells. Homer’s isolation of these two figures underscores the monumentality of their task: the elemental struggle against a sea that both nurtures and deprives.”

Life & Death

Font for “Life”
I love how this is a graffiti font set against a Gothic metal style.
• City Life by Andreas Marinos

Font for “Death”
• Death Crow by Senzana

Image: Life-Size Black Bass, 1904 (via CC0 Public Domain Designation)

Caption: “With trademark ambiguity, Homer presented the bass suspended between life and death. Will it succeed in grabbing its bright target only to seal its fate? The fish’s sudden jump slices through the dark, quiet jungle with a momentary flash of life and color.”

Croquet & Flirt

Croquet Scene, 1866 (via CC0 Public Domain Designation)

Font for “Croquet”
Sadly there is no font named after “Croquet”. Instead, I searched for Victorian.
Great Victorian by Dharma Type

Font for “Flirt”
Only one font exists with the name “Flirt”. At first the lack of legibility was a turn-off. But once this got typeset into the layout, I actually really like it.
Flirt Bobo Bold by Federico Selmi

Image: Croquet Scene, 1866 (via CC0 Public Domain Designation)

Caption by me (not from the Art Institute): The man crouching down is either repositioning his croquet ball, or he is being flirty with the woman in the red and white dress. The woman in the blue dress is either shielding her eyes from the sun, or she’s trying to not watch this man’s flirting actions. Thus, this man is either playing the game of croquet or he’s playing the game of flirtation.

Relaxed & Resigned

Font for “Relaxed”
Three fonts for “relax” exist. This one captures the feeling of being relaxed. I wrote about why I designed these compositions. As an example of why I really like using internet fonts, I did a little more digging into this creator, and found out some really cool things. Check it out in my blog post, “Why did I illuminate Winslow Homer with free internet fonts?
Relax by “put out into the deep”

Font for “Resigned”
No fonts exist with the name “resigned”. Instead, I searched for “lose”.
Nothing To Lose by Jonathan S. Harris

Image: The Gulf Stream, probably 1899 (via CC0 Public Domain Designation)

Caption: “the impassive (or dazed) expression of the castaway and his surprisingly relaxed (or resigned) pose imbue the subject with ambiguity.”

Threatened & Beautiful

Winslow Homer North Woods Club, Adirondacks (The Interrupted Tete-a-Tete), 1892 (via CC0 Public Domain Designation)

Font for “Threatened”
We knew some of the results would be ugly fonts, and this is certainly an ugly font. Wow. This font is the only one with “threat” in its name. This layout was the hardest to work with. I was debating on not including this image in the list, but I wanted to show how some of these just didn’t work out.
Threatened by Hatemachine

Font for “Beautiful”
Many many options for fonts with “beautiful” in the name. Since I was stuck with the “Threatened” font, I picked a beautiful font that somewhat matches. The flairs at the top of the letters in this font match the bursts in “Threatened”.
Beautiful Roses by Bangkit Tri Setiadi

Image: Winslow Homer North Woods Club, Adirondacks (The Interrupted Tete-a-Tete), 1892 (via CC0 Public Domain Designation)

Caption: “In North Woods Club, Adirondacks (The Interrupted Tête-à-tête), hunting is only hinted at in a subliminal way. Homer pictured two white-tailed deer, a doe and a buck, at the edge of a mountain meadow. Homer selected the exact moment when the deer become aware of another presence, the identity of whom is left to the viewer’s imagination.”

“Two tall white pines stand silhouetted against the view, echoing the two deer. White pine had been dangerously over harvested in this period, and worry over its dwindling numbers in the Adirondacks paralleled concern for excessive hunting of deer. Homer drew the pine trees and deer carefully in pencil before adding watercolor, making sure that the distinctive characteristics of both threatened species would be clearly identifiable.”

Neatly attired & Rustic

Netting the Fish, 1889 (via CC0 Public Domain Designation)

Font for “Neatly attired”
Why did I go with a bitmap font for this one? There were several other fonts with the name “Neat”, but I went with this one, because the forms in the font are so regulated. The repeated bumps make it very straight-lined.
Neato by memesbruh03

Font for “Rustic”
The Rustic by Nirmana Visual

Image: Netting the Fish, 1889 (via CC0 Public Domain Designation)

Caption: “Young, well groomed, and neatly attired, the fisherman in this watercolor stands in contrast to the rustic guides featured in many of the artist’s other Adirondacks works.”

Expressive & Protecting

Font for “Expressive”
The Expressions by Java Pep

Font for “Protecting”
There are a couple fonts for “protect”, but none of them fit. Instead I searched for “defend”. This font gives a good strong feel.
Urban Defender by Iconian Fonts

Image: Campfire, Adirondacks, c. 1892 (via CC0 Public Domain Designation)

Caption: “The tree’s roots are expressive formal elements in their own right, but these ancient tentacles also seem to protect the resting man.”

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