The Wild, Wild West of Late ’90s Shareware Fonts
by Matt Scott Barnes
Introduction / Lead Off
The basics: you’d insert the disc and let it load up. You are prompted a list of folders, majority of these CDs were crudely put together and the file names were partial the font name and a handful of underscores. You would select a file and drag a font into your system, double-click, and cross your fingers it didn’t break your machine. Inside the directories lived a typographic graveyard: Helvetica, but weirdly stretched versions, a few bootleg Comic Sans, and somewhere in the mix, you would find an occasional treasure, a wildly beautiful display font. These CDs brought me my first chance to use Cooper Black and in multiple weights. Also, they helped me realize that the magazine Thrasher’s masthead was set in Banco.ttf, which I discovered on one of the discs and immediately started using it on flyers for a show I was promoting. I also remember the font named Igloo, and from my digging around it was also known as Ice Caps, it’s the gas-station ice cooler typeface. It’s kind of like a feeling of randomly finding something like a secret, right? You instantly think, "I've discovered something new." It makes you feel like a type archaeologist digging through digital junk, or maybe a hacker finding a hidden file. That's how I felt when I found Bedrock, where the letters look like someone just chopped them out of cardboard with an X-Acto knife.
Dr. OS/2
by Dr. CD ROM
1993
No License, No Masters
There were two types of products that defined them: Freeware and Shareware.
- Freeware involved distributing fully functional software at no charge. The author retained copyright but waived the usage fee.
- Shareware, however, is operated on a trial basis. It allows users to test a full or limited version for free but were encouraged, and expected, to pay a fee for continued access, unlocking any extra features.
These two concepts were fundamental to this CD-ROM economy. The font packs were filled with both, with a large percentage given away by designers as Freeware, while others were Shareware demos, often including only the regular weight, with additional styles included when purchased. This method of distribution completely bypassed traditional foundries or conglomerate licensing systems, allowing anyone with a bootlegged copy of Windows 98 and a CD drive to experiment with typography on another level that I had never experienced previously.
This is an embrace of a sidelines distribution and it reflects a core principle of postmodern design, which Rick Poynor described as rejecting "professional design's orderly methods and polite conventions, revelling in deviation and chaos and refusing to acknowledge any such category as 'error'" (Poynor, 2003, as cited in SOAR). The availability of a thousands of fonts even if it’s a mix of "good taste, poor taste" its presented at the same level, if sometimes messy, typographic landscape that effectively promote a "post-taste, post-style" era where the old rules of Swiss modernism no longer applied (Keedy, n.d.). The CD-ROM distribution, much like the underground press and punk culture before it, proved that a low-cost, decentralized distribution was a powerful engine for cultural experimentation (OpenEdition Journals, 2022). It made the era for me both never ending and exciting.
Dr. OS/2
by Dr. CD ROM
1993
Letraset but digital: Font Is Corrupted
However, this democratization came with high effort and high risk. Letraset demanded time for searching for the right letter on the right sheet of type. You would then cut it out, delicately line it up, and rub it down onto your final piece. Each transfer was a leap of faith; an old spent sheet or a slight movement would throw the letter off the baseline. Even so, through this process a new aesthetic was created.
The tactile, error-prone nature of this process—often combined with collage and found imagery—was the hallmark of a new, anti-establishment visual culture, particularly within punk graphics (Poynor, 2003). As Soar notes, this era was defined by the "scissors and glue" approach, which fostered an aesthetic of visible labor, randomness, and non-professionalism (Soar, 2025).
The freeware and shareware CD-ROMs delivered a new version of this, being digitally different, but similar without so many limits. For example, my discovery of the font Lower West Side—a digital revival of the Letraset-produced face Shatter—showed the final evolutionary step. Where the dry-rub lettering of Shatter was permanently fixed and inherently limited, the digitized Lower West Side became limitless and editable on the computer. The lowbrow spirit of Letraset had successfully crossed into the digital world, replacing the physical limitations of the sheet with the endless possibilities of the file.
Dr. OS/2
by Dr. CD ROM
1993
Gutter Spelunking
These CD-roms were worth more than 5 bucks I paid for them. They were introductions of experimental typography. Aarcover (AARCO___.TTF), a wild lightning bolt font, that works for everything, while Hobo, the bell-bottomed font you see all over Vermont ski towns.
Somewhere deep in those folders, I found David Rakowski. Not and explanation of who he was or that I even knew who he was at the time, but I found his work scattered through the disks, tucked between Comic Sans wannabes, Enya Font, and other absurdities.
From there, my research brought me to Dan Solo. Dan Solo was not a type designer, he was a collector. He saved and persevered type specimens, he assembled archives of type from blocks to phototype by lots of unnamed typographers. These collections might have been lost to time with out his collecting and sharing. I found even on my own bookshelf a Dover book that was a collection of Solotype, Special-Effects and Topical Alphabets, Which showed me printed specimens of the collection before they were digitized. Other designers, including Rakowski, likely took these printed collections and turned them into working digital fonts.
Rakowski’s submitted fonts in these packs were stood out in the folders on plain san serif mediocrity. His selection that he submitted were lively and musical, it showed me someone was experimenting and having fun with what fonts could be. Solo’s collection provided the inspiration, the printed evidence of what had come before, and Rakowski and others did the legwork of digitizing, cleaning, and making them usable on your system.
Among these fonts, I saw Shatter as it stood out. Wildly, it was originally produced through a contest by Letraset. It was produced as a dry-rub lettering sheet, Rakowski renamed it to “Lower West Side” when converted to a working font. Lower West Side, as Shatter it was limited by what was provided, but now it has become limitless, and editable.
Live Wire: High Voltage Typeface
“Aarcover is an all caps Type 1 PostScript font, plus numbers and punctuation, whose characters look like static electricity or limp lightning. It was done at the request of a group called, oddly enough, AARCOVER. This font was made on a Mac and converted with Wrefont for use with ATM/PC. No warranty is expressed or implied as to its working as expected. No warranty is made as to its functionality when ported to any platform other than Apple Macintoshes.
Aarcover is shareware, with the following terms: if you use or keep it you must do one of the following: send a check that will not bounce in the amount of $12,341,709.12 to Cynthia Lemiesz at the Columbia University Music Department, 703 Dodge Hall, Columbia University, New York, NY 10027; send a crisp one dollar bill to the same address, along with a blurred photograph; or bow on your knees every day for twelve days and face Spencer, Massachusetts, repeating the mantra, ‘I like jam! I don’t understand!’ for 18 minutes.
Aarcover is © 1991 by David Rakowski, who holds onto Insect Bytes until they stop itching.”
It made a joke of early day licensing, but also a created a new idealogy; some things are meant to share and be put out into the world, to mutate and be used.
Preservation, Legacy, and Dafont as Punk Zine
It was much later in my career, revisiting these discs, that I first encountered Logger. That stacked log font, perfectly at home on a Vermont ski lodge marquee, pulled me right back to the feeling of exploring those original CD-ROMs. Many of these digital artifacts survive today. Sites like Dafont.com and FontSquirrel maintain as archives of early freeware and shareware fonts. These repositories are like the fan zines of digital typography. no rules and free to experiment without much of a critique. They celebrate equally the beautifully crafted and the ugly. Its kinda like anyone with access to a Xerox machine could produce a zine on their favorite local bands and bars in the 1980s, to anyone with Fontographer or FontLab could release a font in the 90s. There really isn’t a scale of what was good or cool versus bad and lame.
When you search enough and you find emerging patterns, the early web-era maximalism, transitional technologies,the rebirth of Letraset and Solo catalogs. Fonts like Lower West Side, Aarcover, Logger, Hobo, and Bedrock coexist with various iterations. Dafont and its kin are archives of experimentation and community, much like punk fanzines preserved music and subcultural visual aesthetics outside main popculture. Contemporary Design culture has long shit talked these sites, but doing so is to miss what actually is there; These sites are living platforms that archive digital folk typography, full of creativity and experimentation.
The Hopeful Future
Somewhere in an attic or thrift store bin sits a cracked jewel case labeled “5000 Fonts for Windows 95.” Inside are digital fossils: early experiments, lost display faces, homemade revivals. And maybe, someday, a new designer will pop one in, not to find the next Helvetica, but to rediscover the charm in a font like Guardian Bold, or wacky display, or a beautiful script that fails so completely it circles back to brilliance.
The hope is that they’ll see what we once did: that fonts are alive, that the past is still editable, and that design’s most exciting moments often start with a bad idea burned onto a cheap disc..