The story about the original Macintosh’s built-in font set being named after “world-class cities” is well known and documented by Susan Kare on the Folklore site:

The first Macintosh font was designed to be a bold system font with no jagged diagonals, and was originally called “Elefont”. There were going to be lots of fonts, so we were looking for a set of attractive, related names. Andy Hertzfeld and I had met in high school in suburban Philadelphia, so we started naming the other fonts after stops on the Paoli Local commuter train: Overbrook, Merion, Ardmore, and Rosemont. (Ransom was the only one that broke that convention; it was a font of mismatched letters intended to evoke messages from kidnapers made from cut-out letters).

One day Steve Jobs stopped by the software group, as he often did at the end of the day. He frowned as he looked at the font names on a menu. “What are those names?”, he asked, and we explained about the Paoli Local.

“Well”, he said, “cities are OK, but not little cities that nobody’s ever heard of. They ought to be WORLD CLASS cities!”

So that is how Chicago (Elefont), New York, Geneva, London, San Francisco (Ransom), Toronto, and Venice […] got their names.

If you check out the actual Philly stops and witness all their provinciality, you can understand what Jobs was after:

Go to first Macintosh via Infinite Mac, open Infinite HD and MacWrite within, and you can examine the nine eventual fonts in their pixellated, cosmopolitan glory:

The list goes in this order: New York, Geneva, Toronto, Monaco, Chicago, Venice, London, Athens, San Francisco.

But: How about some hard evidence for the original anecdote? Turns out, the March 1984 issue of Popular Computing used pre-release Mac software and printed a screenshot of the names rejected by Jobs:

Since on the facing page we see the output in the same order, coming up with the correct mapping is not hard:

• Cursive → Venice
• Old English → London
• City → Athens
• Ransom → San Francisco
• Overbrook → Toronto
• System → Chicago
• Rosemont → New York
• Ardmore → Geneva
• Merion → Monaco

One has to admire the final order of the Mac fonts that went from dependable and utilitarian at the top, to progressively more weird; this earlier list is all over the place.

In later releases of Mac OS, three other world-city fonts – Boston, Los Angeles, and Cairo – joined the party, so let’s show them here for completeness’s sake:

(Cairo is the classic icon font and in a way a predecessor of modern emoji, with inside jokes like Clarus The Dogcow.)

But that’s not the end of the story of the original Mac fonts. Let’s get back to 1983. On yet another page of the magazine, we see this list from MacPaint:

You can tell this screenshot is even older than the previous one, because it is itself set in an earlier version of Chicago, with a single-storey lowercase “a,” and many letterforms being works in progress. (I talked about the history of Chicago in my 2024 talk about pixel fonts.)

And it is old enough that this isn’t just interim names for surviving fonts – it’s actually quite a few old fonts that didn’t make it to the release day.

Unfortunately, this particular version of Macintosh software remains unknown, but one similar pre-release version of the first Mac software leaked, and so we can take a look at some of these fonts, too:

(You can download a lot of these fonts thanks to the hard work of John Duncan. They are still bitmap fonts and might not work in all the places in modern macOS, but they seem to work in TextEdit at least.)

Here’s what I learned from looking at this list:

• You can definitely see how unpolished some of these fonts are in terms of spacing, letterforms, and available sizes – kudos to the team for holding a high quality bar even though there was little precedent for proportional fonts on home computers at that time.

• Even the fonts that shipped – London (née Old English), Venice (née Cursive), and Chicago (née System) – have had their letterforms tweaked and improved.

• Chicago is not named Elefont, but simply System. Had the System name persisted, this Medium snafu from 2015 would have been even more hilarious.

• The name of the monospaced Elite font is likely inspired by one of the two classic sizes of typewriter fonts: pica (larger) and elite (smaller).

• Cream came all the way from Xerox’s Smalltalk and was the original system font for Macintosh-in-progress, before Susan Kare created Elefont/​Chicago.

• PaintFont was a symbol/​icon font, but distinct from Cairo and emoji in that it seems it was meant to be used only by the app to draw its interface. (Today, SF Symbols serve a similar purpose.)

• Apple originally planned to use Times Roman and Helvetica, but this hasn’t happened presumably because of licensing issues. Only years later, the proper Times and Helvetica fonts were introduced. Here’s a comparison:

But the most interesting thing I haven’t noticed before are two fonts called “Marie Osmond” and “Patti.”

I am reaching outside of my well of knowledge here, but from context clues I’ll assume the latter means Patti LaBelle. And so, pulling on that thread, it’s kind of cool to imagine an alternate universe where the original Mac fonts are neither suburban Philly stations, nor well known cities, but something like this:

I occasionally move older writing that still feels interesting to my new site, and today I republished the 2015 story about a strange bug that brought back an old pixel font from beyond the grave:

Some of the technical details inside are obsolete, but the story might still be fun. (Plus, it seems like at every job I have, I eventually stumble upon a bug that brings back something from the annals of history. Here’s one from 2019.)

It’s hard to imagine it now, but during iPhone’s first year, no emoji were available at all. It took four years until 2011’s iOS 5 gave everyone an emoji keyboard.

But in between 2008 and 2011, there existed a peculiar interregnum where emoji were only available on Japanese iPhones. The situation had to be carefully explained and caveated:

Eventually, an enterprising developer realized that emoji outside Japan was as easy as toggling a UI-less preference with a great name KeyboardEmojiEverywhere, hiding inside the innards of the iPhone:

Except, “easy” is in the eye of the beholder. This was still a few too many hoops to jump for an average iPhone user. So, developers figured out that there could be an app for that: the above preference incantation wrapped inside an application with an easy UI, and put in the burgeoning App Store.

The interesting part is that Apple initially fought some of these efforts, by rejecting a Freemoji app and likely a few others. (Not sure if this was about emoji specifically, or more principally about losing control.)

The developers had to get sneaky, and started hiding emoji enablers inside other apps. A $0.99 “RSS reader for a Chinese Macintosh news site” called FrostyPlace unlocked emoji by “simply pok[ing] around in it for a minute or so by tapping in and out of an article and playing with the two buttons at the bottom of its screen. That part is important, so be sure to do some genuine tapping.”

Then there was the free Spell Number (you can still see its old App Store page), where punching in a certain secret number would give you the same.

The author called it an “easter egg” and even wrote candidly at the end of instructions that “you can also delete Spell Number if you don’t want it, the setting will still be here.” (The number also had to change from 9876543.21 to 91929394.59 at some point, perhaps to evade… something?)

Eventually, Apple seemingly gave up – Ars Technica has a fun interview from 2009 from someone who renamed their app from Typing Genius to “Typing Genius – Get Emoji” and got away with it:

Ars: As the screenshot at the start of this post shows, you haven’t been shy about advertising the Emoji support over at App Store. Are you worried that adding Emoji to your application might have negative consequences? Are you worried about Apple pulling it from App Store?

Fung: I’m obviously taking a risk here by advertising Emoji directly on iTunes. That being said, I’m not the first. Worst case scenario, I’ll update the application with Emoji support removed. I’m hoping that Apple will turn a blind eye to this because I can’t see any harm done in allowing users to use Emoji.

Not quite “I am ready to do some time for the good cause,” but close enough.

Yet, it still took until 2011 for emoji support to be universally available with iOS 5, and even then you had to enable the keyboard in settings.

I like this little story of a mysterious latent cool new thing hiding inside your device, a thing that you could unlock only if you followed some seemingly nefarious instructions that never fully made sense but that actually worked.

An interesting tidbit: At least early on in 2008, for emoji to work both the sender and the recipient had to follow the instructions. So the toggle wasn’t just about adding a keyboard, but also enabling the decoding and rendering. (And complicating things further, iPhone’s Japanese keyboard had emoticons, and that keyboard was widely available without any hacks. The difference between emoji and emoticons was not obvious to many people, leading to a lot of extra confusion.)

Lastly, a fun sidebar: I asked about all this an old internet buddy, Steven Troughton-Smith, whom I remembered back from my GUIdebook days, and who still routinely posts fun hacks and discoveries about Apple platforms on Mastodon. I thought “Steven might remember that story; he seems like the kind of person who’d at least know how to find an answer.” Turns out, my hunch was better than I thought: Steven was the enterprising developer who actually discovered how to give emoji to any iPhone, all the way back in 2008.

From May last year, a 21-minute video by Linus Boman about font piracy, specifically during the era of personal computing and early internet:

The nuances of what separates font piracy from non-pirated revivals or general inspiration are too much even for me, but I liked how the video moved on from the obvious and cheap “haha, you wouldn’t pirate a font” story to cover a few of the more complex issues with panache.

My small contribution to the discourse is that I just scanned an interesting booklet from 1979 called Typeface Analogue, which catalogs various names different phototypesetting manufacturers used for their “replica” fonts – a sort of a translation table between once-relevant parallel type ecosystems.

Some are pretty uninspired: CS for Century Schoolbook, OP for Optima, Eurostyle for Eurostile, and so on. Others are more interesting: a version of Palatino called Patina, American Classic becoming Colonial, or Futura renamed to Twentieth Century. Absolute fav? Helvetica becoming Megaron.

The display fonts you see on this blog are my vector conversion and slight improvement (kerning pairs!) over a bitmap PC/GEOS font called University, which itself was inspired by the original Macintosh’s Geneva. Inspired or downright stolen? You decide:

A fantastic 37-minute video by Nic Barker that explains ASCII, Unicode codepoints, and their relationship to UTF-8, UTF-16, and UTF-32.

I learned a lot, and I never thought I’d walk away from the video appreciating the craft of text encoding. Also, really good storytelling!

This is neither the first nor the last time I’m sharing David Jonathan Ross’s work; today I want to link to a really fun glyph explorer he put together recently:

That’s it. That’s the tweet. On this blog I generally want to capture the meaning of well-made things, deeper thinking, going beyond cheap sugary delight, the discomfort of rigor meeting joy and craft colliding with function, and the “why” of it all – and a lot of that is actually all here, too, as long as you keep clicking on things.

But: sometimes it’s also just so nice simply to look at beautiful letterforms for a while.

(Also available on Masto and on Pixelfed.)

I was reminded of and rewatched this 43-minute 2016 talk by David Jonathan Ross with great interest:

Ross designed Input, a coding font superfamily which was very inspiring to me in the day, and taught me that coding fonts could be a place of surprising creativity and innovation.

First of all, Input has four width options: from regular through Narrow to Condensed to Compressed – this not only allows to avoid the “blocky/​squareish” nature of many coding fonts, but also, pragmatically, to squeeze in more stuff on mobile screens.

Secondly, since a lot of coding environments didn’t (and maybe still don’t) allow for fine-tuned typography settings, you can bake them into a font upon download – choose a different default line height to be there in the font itself, or have your favorite style of zero just hanging there in the default slot.

Thirdly, serif versions of Input coexist with sans serif, and so does italic, and you can mix them together.

But most important thing comes at the end: you can imagine coding in non-monospaced fonts! What seemed like blasphemy before made so much sense once I put it to use – I still code in Input Sans Narrow (non monospaced) to this day:

Of course, since the release of Input in 2014 a few other coding fonts did interesting creative things in this (mono)space. But to me this will always be the original that opened my eyes to what’s possible, and the talk captures so well a lot of deep thinking that went into the font. To quote Ross:

Type design is design and design is about solving problems.

You might not encounter them often in polished fonts unless you’re knee-deep into typography, but: fonts have bugs, too.

Paul van der Laan on Mastodon:

Did anyone ever notice that Avenir LT has some serious errors in the descender lengths of p and q in certain weights?

Florian Hardwig adds:

It’s one of the things that got revised in Avenir Next. But it’s bonkers that it hasn’t been fixed in the “legacy” Avenir that’s still being sold – and bundled with Mac OS – after all these years.

Downthread there’s an original Avenir drawing that for some reason I found very evocative:

I hate most font reveals; they’re written in a pretentious, corporate-meets-Design-with-capital-D way that’s devoid of any value or meaning or feeling, with the requisite highly polished motion graphics that feel pretty like empty sugar calories. They did feel like written by AI before that became a meme.

This feels like the opposite: an actual personal font announcement of Shantell Sans that made me feel things. From Shantell Martin:

When I was 20 or 21, I found out that I was dyslexic. When I started my art degree at Central Saint Martins in London, I was in an environment where it felt like the majority of people were dyslexic. I was instantly part of a cool group of creative people. However, I was disappointed about the amount of teachers who had never spotted my reading challenges. Instead of supporting me to learn to read and write, they punished me.

What I liked about this post is that it hands the mic off to other involved people: Stephen Nixon who “produced” the typeface, and Anya Danilova who took care of the Cyrillic side. It’s a simple technique, but I feel much more effective than doing the “oral history” a.k.a. “journalistic” approach of different people having various quotes interspersed. It can work, but only if you do it really well. Almost no one does it really well.

There’s just so much to love here. The motion graphics are actually useful, informative, and allow you to learn things! Even the “in use” photographs are delightful and don’t feel arbitrary.

Just well done all around.

(Also, I hate Comic Sans, so having something new in the same vein will be genuinely useful.)

I was just looking at some old 1980s screenshots and wondering “why don’t you ever see syntax highlighting in inverse video”? And then I randomly stumbled upon this deep dive into syntax highlighting from Nikita Prokopov.

I don’t know if I disagree with everything here, but there’s a lot of great stuff in there, and a lot of food for thought.

Highlighting everything is like assigning “top priority” to every task in Linear. It only works if most of the tasks have lesser priorities.

I thought the mention that comments should be visually promoted, not demoted, was particularly insightful.

Also, the idea that light themes are not popular because the colors are duller… this is very interesting. It could be so interesting to try a light theme with very prominent chiefly at the periphery of Display P3.

I have never been very invested in syntax highlighting because I find the UI to change it in text editors is usually pretty harrowing, but now I’m interested.

Oh, this is a fantastic adage I haven’t heard before, mentioned here in 1978, arguing against distorted, or “faux” typography:

A Linotype assembly elevator with the gate closed. This is the center of an operator’s attention as the mats tumble down and are arranged automatically in lines. The spacer bands adjust themselves to fill out the line but only so many letters can fit in any measure, proving the old trade adage that “type is not rubber.” Modern photocompositors have lenses that can distort the image of the letters to fit where they couldn’t. Today, type is rubber.

I’ve always been curious whether those “dyslexic-friendly” fonts amount to anything, and this 2022 post I haven’t seen before puts this idea to rest:

But the new fonts—and the odd assortment of paraphernalia that came before them—assume that dyslexia is a visual problem rooted in imprecise letter recognition. That’s a myth, explains Joanne Pierson, a speech-language pathologist at the University of Michigan. “Contrary to popular belief, the core problem in dyslexia is not reversing letters (although it can be an indicator),” she writes. The difficulty lies in identifying the discrete units of sound that make up words and “matching those individual sounds to the letters and combinations of letters in order to read and spell.”

(via Daring Fireball, whom I quoted for the title, via Jens Kutílek, whose fonts I use)