I released Jillsville on August 14, 2002 as a paid typeface. The name came from my earlier play with the soft “Jill” sound in Jillican; I had considered calling it Coolsville because I wanted something that sounded like a cool town, but Jillsville felt more distinctive. At first it came in two styles—Regular and Bold—which were so light that the difference between them was minimal. The design itself came from a mistake with a typewriter and carbon paper, where overstruck letters left small ring shapes that inspired the letterforms.

On September 14, 2009, version 3 expanded the character set with more Latin accents and punctuation, and it introduced class-based kerning. By 2017 I decided the typeface needed more than adjustments; I rebuilt it from the ground up. The new Jillsville expanded into seven weights with matching italics, with spacing redone, punctuation replaced, and fractions supported. I also added Greek and Cyrillic support. The letterforms were so extensively revised that the result was essentially a new typeface, though it kept a thread of resemblance to the original.

Version 4.1, released in November 2024, refined naming conventions, renaming Ultra-Light to Thin and modernizing the overall structure for application compatibility. That update also fixed the encoding of the single base quote to improve cross-platform consistency. Jillsville never had any notable usage in the wider design world, but for me it marked a transition from a quirky experiment into a more substantial, multilingual family.