I know I’m usually driving the Finder pretty hard, but I think that’s a necessity, given its position as the center of macOS for power users, and its situation where it feels like Apple pretty much gave up on it.

But I also want to show things that Finder does well, and this might be something no one does nearly as thoughtfully: text truncation.

This is what happens when you have a filename that’s too long:

This is really nicely done, for many reasons that work in lockstep:

• Finder cleverly elides text from the middle, knowing that both the ending of the last words (or digits!) of the file name, and its extension are important.
• Finder shows the full name in a tooltip. I’m surprised how many tools forget to do that, offering no easy explanation for the missing letters. Here are some examples from Notion and Bear, neither of which offers help on hover:

• Finder position the tooltip exactly atop the existing text. I think this is really clever: it avoids overlapping other useful information, and makes it faster to reorient yourself. Compare with, for example, AirTable:

• Lastly, Finder only shows the tooltip when it’s needed. This is something where so many places lose their way. For example, here’s Paper and Google Drive, throwing up a tooltip indiscriminately, even if it has absolutely nothing to add to the conversation:

Why does this last thing matter? Because unnecessary tooltips are distracting, cover information, and also – maybe most importantly – turn the interface into a minefield where no safe places remain to just mindlessly rest your cursor without worry.

This last thing is very fuzzy, but so important. You know how unpleasant a lot of articles are on the web these days, solely because you’re always on the edge about what’s going to happen while you read? Am I going to be moved up and down? When and where is the ad going to appear? When will I encounter a new subscription pop-up, and what will be the weird way to close it this time around?

I know you don’t literally tense your muscles while reading those, but I feel like in some sense, in the back of your head, there is always this unpleasant worry that you’re dealing with an unstable interface.

This is not a strong, but I feel a similar way about spurious tooltips; they make interfaces feel less stable. You rest your cursor, something jumps up at you, you get distracted and move your cursor instinctively to avoid it, and with any luck, you trigger yet another tooltip, and so on.

I will write more about this in the future. If you asked my former coworkers, I bet a significant portion would say “this guy gets angry at tooltips, like, all the time.” I promise I will get angry at tooltips more here. But today? Today, kudos to the Finder. It shows us that if you care, you can make this small moment feel really great and thoughtful – knowing that small moments multiplied in the thousands are no longer small.

In my three decades online, it has never occurred for me to try this, and I found it so delightful once I did – both Chrome and Firefox will quietly rewrite backslashes in URLs into slashes:

Not Safari, however, even though the URL living standard says it should.

I am very curious if the presence of backslashes in URLs is owing to Windows still showing backslashes in file paths, or just because people casually don’t see any difference between / and \, which are arguably both similar, and relatively alien in everyday typography. (“Solidus” is the proper typograpical name for this kind of a slash, partly to disambiguate it from all the other slashes with their equally fascinating names.)

For a while, the digital artist James Dalzell Hodge kept a video diary of various design decisions while making his next game. This 13-minute video is interesting because it harks back to my mention of diegetic interfaces just a few days ago:

It’s a nice quick dive into the subject – a rare coverage of what “diegetic” means outside of the realm of movies.

I like these videos because Hodge focuses on details and shows working through things, including approaches rejected along the way. Inside, there are even occasional peeks at interfaces from Unreal Engine tools and Blender, not to mention examples from other games.

I thought about this the other day, and I thought it’d be fun to share this internal tool I made over a decade ago to aid with exploring options for Medium’s typographical redesign.

It’s called Fontificator. You can play with Fontificator here (desktop browsers only), or watch the likely confusing video below:

The motivation for building Fontificator came from two observations:

• font previews on type foundry sites were generally too limited to get a real sense of how a certain typeface feels, and it was best to see a font in situ,
• often an extremely tiny nuance – like adding some letter spacing, or messing with line height – was what separated something that was promising from something that seemed very far from working.

With Fontificator, I was aiming at this Doug Engelbart-esque notion of one hand on the keyboard + one hand on the mouse, and the UI where it was only necessary to point to an element, and the keys under your other hand would start working immediately – no clicking needed:

• F and G to change the font,
• – and + for font size,
• ← and → for letter spacing,
• ↑ and ↓ for line height,
• < and > for opacity (for all the above you can hold Shift for bigger moves),
• and, there are a few more shortcuts you can see at the top.

This way, we could move really, really fast. To accommodate that, Fontificator always tried to keep the current item under the cursor by counter-adjusting scroll position as needed.

On top of it all, a few more shortcuts:

• ⇥ and ⇧⇥ move very quickly between different types of stories so you can preview that,
• Space compares to the original/​current version,
• 1–9 allow you to switch to different “slots” so you can have various presets ready to compare,
• Esc hides the toolbar for maximum immersion,
• ⇧R resets.

You can also edit any text if you are so inclined, and also drag in any font file from your computer onto a paragraph – then that font becomes part of the F/G stack. (Bernino Sans and Freight Text were the starting fonts before the redesign.) On the left, you can also see a naïve mobile preview – there was also more sophisticated on-smartphone preview, but I removed it from this restored version.

Fontificator was literally made for an audience of 2–3 designers (and perhaps 1–2 stakeholders in read-only mode), and it was surprising to me how quickly one could master this strange tool, have fun with it, and feel the page’s typography becoming much more malleable. We also put up a more “traditional” list of contenders on the wall…

…but it was in Fontificator where we learned the most.

I love internal UIs because they allow you to go very wild and very tactical. If you have one you’d be willing to share (maybe it, too, is on the other side of the statute of limitations?), or one you already wrote about or spotted someone else doing so, please let me know!

A reader sent me this screenshot from PowerPoint, with one of the menus looking the best it’s ever looked, and the other one showing to work with what we could charitably call “a UI hangover”:

It’s obviously bad craft and crossing over to the “embarrassing” territory, but I thought it’s an interesting question: what happened?

The main piece of the puzzle is that the first menu shows the name of the font in San Francisco, but the second asks to render the font name in itself, serving as a font preview.

Font previews are fascinating because they are the perfect showcase of how tricky fonts can be at scale.

Some time ago, I wrote an essay called Typography is impossible. TL; DR: It’s actually impossible to left align or center text. Ever. Not just because each font does whatever it wants – font size is a number that doesn’t really give you anything to hang a hat on, and the font can place itself in its box however it desires, too – and not just because fonts often lie (via bad metrics) about what they store inside, but also because aligning and centering are really in the eye of the license holder, and have more than one definition.

So, every time you align text to anything, in whatever way, it’s only an approximation. Most of the time that’s good enough. Here it is not.

I worked on font previews at Figma, and wanted to show you three screenshots of what we did.

This first one shows the default attempt: we ask the fonts to render themselves in the same size (16px), vertically centered in a box that’s always 28px tall… and they oblige on paper, but it really doesn’t feel like they are:

The second take shows what happens if you nudge the fonts up and down so they’re aligned to their baselines. This at least creates vertical rhythm; in effect, we need to make the fonts uneven to make them feel even.

And this is the final result, with extra adjustments:

What do we do in the final version? Too many small things to mention, but in essence:

• We literally measure the fonts (programmatically) by rendering them and looking at them, and make adjustments. We blow them up (but not too much) if they’re optically too small, or reduce them (but not too much) if they’re too big.
• We have a multiplier for scripty fonts and monospace fonts, where the traditional measurements are likely to be off.
• We even special-case specific fonts by name. That feels like bad practice, but fonts are so varied and all over the place, that I think it’s perfectly fine to make exceptions for particular individual fonts that are popular or otherwise very important to your users.

These adjustments are all in the same category: getting off math balance to get to optical balance.

Here, you can compare before (the naïve version) with after (the final version):

If it feels subtle, imagine it applied to a much wilder menagerie of very thin, very huge, or very strange fonts. (The go-to example? Open a Mac and try typing in Zapfino.)

I’m not showing this to brag about my work – okay, fine, to some extent I am, we’re all human – and I truly believe this could be so much better, still. There are icon fonts, color fonts, and non-Western fonts so rich in variety and tradition that this category itself is basically a fractal.

Mostly, I wanted to share this lesson: dealing with fonts is hard, and dealing with fonts as a system even more so. Whether it’s the printing press, paper, or Illustrator, it takes people years or even decades to fully learn the craft of setting type, and to believe their eyes instead of only relying on math. But here, what’s needed is manufactured craft: we have to teach the machine to trust its eyes (which it doesn’t have) over math (which it can’t escape).

Now if you’re wondering why font previews look bad in so many apps, I believe it’s because people working on those did not allocate enough time to deal with all that.

But I’ve used the word “embarrassing” as there’s one more thing that the original did poorly, and something the reader identified immediately. The makers of PowerPoint allowed the font to escape its containment:

This is another big lesson: fonts will ignore their bounds at every single opportunity. That infamous CSS IS AWESOME graphic? That’s CSS underestimating text. That naked URL or code snippet pushing the mobile site past the viewport and making it scroll? That’s the creators of the site not building up enough imagination of what fonts can do when they’re not watching. Zalgo text? A joke, but based in reality.

Fonts are so much more feral than you think. Are you ready for it?

Thank you to Giovanni Lanzani for sending in the original PowerPoint screenshots.

A nice moment in the iOS emoji keyboard – after selecting an emoji from the grid, its name shows up for a second:

I have small reservations here, as reusing a placeholder like this trips up my “this is cheap” alarm. But otherwise I like that this – just like keyboard shortcuts in menus or tooltips – ambiently teaches you the alternative representation of the emoji that you can use later to get to it faster.

(Another way of looking at it: This is a tooltip in a place where tooltips cannot exist.)

This is not italics. This is not even oblique. This is a side effect of how those displays work. Instead of a whole rectangle of pixels being changed at once, the display is updated line by line, starting from the top one. As it’s moving towards the bottom, the internal horizontal position might have already advanced, the subsequent lines will be drawn slightly to the left, and it all leads to a slanted appearance. (This is in effect the same problem as rolling shutter in photography.)

The interesting thing is that it could’ve gone the other way. Twice. In English or German, we treat scrolling left to be natural, and we consider only one direction of italic slant appropriate. The first has to do with the direction of reading. I believe the second is, like many things in typography, customary; there’s nothing inherently better than right-leaning letters, except we’re used to them since those are the only ones we ever see.

But, the person putting it all together could’ve just as well done it the other way: scrolling to the right, or slanting to the left (by updating the display bottom to top – not as unusual as you might think!). Were those intentional choices, or was it a default? I’m not sure, but it points to the value of knowing this stuff, or creating a culture where this stuff is treasured. Often, more craft will require more work. Sometimes, however, you will get it for free – but only if you choose the right fork in the road.

While we’re here, how about a few other examples of delightful moments in typography where I did not expect them? These, I believe, will be all intentional. But whether you consider them craft, or even good, I don’t know.

Here are some surprising small caps:

Here’s a cute depiction of a train carriage, somewhat hampered by the limitations of a similar workhorse 5×7 pixel font display:

But here’s something even better. This icon of a stadium cleverly leaned into the same limitations. It’s so delightful. These are, I believe, four characters side by side:

Here, someone added nice decoration to fill out the space:

Here, someone removed all the line height to create a fascinating vertical ligature. This is Gorton and the letters are carved into the plastic, so this required some effort!

Speaking of obliques, this NOT is too thick, and slightly too large, but you have to appreciate someone actually slanting the text rather than underlining it, or decorating in a simpler way:

Even if you underline, you can go a little… well, below and beyond:

Or, here, with maybe the most impressive, three-dimensional underline I’ve ever seen:

This I spotted on an old typesetting machine, and I would like to believe this is an intentional easter egg:

This was on a computer keyboard. You don’t expect hyphenation in this context…

…and you definitely don’t expect an old-fashioned contraction:

I hate lorem ipsum with passion, but guess what? There’s more intentionality in it than I assumed, and even easter eggs, as this fun 25-minute mini documentary from Emily Zhang/​Rabbit Hole shows:

You can tell that this was not the work of an amateur. The garbled text is done with a lot of care and knowledge. You can see a lot of rational decisions about why it looks the way it does in there. They are making very careful additions, such as adding letters… the “-and”s and the “-ng”s… The “y” got stuck in because that’s an English letter. […] I think the fact that it is garbled Latin text, and that it has those other letters in a fairly Latin-based alphabet amount of frequency, speaks to that it was done very, very carefully.

Just a fun watch all around.

In last week’s post, I made an off-hand comment about Vercel’s Geist Pixel announcement, and I thought it might be interesting to turn this into more of a full-fledged critique.

I don’t think it’s a good announcement, but its flaws are pretty universal, so I want to put words to these flaws. This will extend to a lot of other writing about design, not even necessary even just about typography.

Here’s my advice that I believe would make announcements like this better:

• Write like a human being would. This is famously hard, and takes practice. Here, we see stuff like “unapologetically digital,” “a functional tool within a broader typographical system,” “the result feels both nostalgic and contemporary,” and “constraints weren’t a limitation, they were the design tool.” No one talks like this. I think people believe font releases have to use these kinds of words and phrases, as a way to bring legitimacy to the project. I do not subscribe to that way of thinking. I think it leads to writing that’s optimized only for admiration, which is not as much fun for anyone.
• Show a specific example of a problem you solved. This page hints at some things – “They don’t scale properly across viewports, their metrics conflict with existing typography, or they’re purely decorative.” – but that feels altogether too vague to be useful or even interesting. These are actually fascinating and hard challenges, yet I know as much at the bottom of the page as I did at the top.
• Show details you are proud of. Zoom in literally or figuratively. “Each glyph was manually refined to avoid visual noise, uneven weight distribution, and awkward diagonals.” I would love to see a few examples.
• Show work in progress! Show stuff you discarded. This will be hard, but why not? It’s good practice and I believe this, more than anything else, will have people appreciate what you did. Plus, everybody loves a blooper reel.
• Related: talk about struggle. But don’t just motion in the direction of challenges, or performatively announce that this was the hardest project of your life. Actually talk about something that was hard, and why. Be vulnerable. Be honest. People didn’t care that Rocky lost in the first movie, because people cared about Rocky.
• Talk about your inspiration or history. What we all do here is part of something much bigger. Why a pixel font to begin with? Why is this interesting to you? Is that because Vercel is filled with nerds, or because you got bored with bold and italic, or because it just seems visually interesting in a new way?
• Let me type! Immediately and on every relevant page. I don’t think any modern font announcement/​tester can exist without this. This is the easiest way to getting to know the font and explore specific things that matter to you. (To do this here, you have to go to the font page, switch to Geist Pixel at the top, and then scroll all the way to the bottom. This feels entirely too far away.)
• Show, don’t tell, generally. The Geist Pixel announcement feels rife for an avalanche of “show,” but has so little. I mentioned above wishing to see examples of manual refinements. There is a visual for “seamless mixing,” but it’s really a marketing photo, not a real-use example – it visualizes what, but you want to visualize what and why at the same time. I would love to see the spread of variants, specific examples of how the font is not “breaking in production” and “scaling properly across viewports.” I don’t know what is a “semi-mono approach” and I would like to learn.
• Motion is okay, but it has zero nutritional value. If you have limited resources, don’t spend it on motion. Anything interactive is better. (But again, the best interactive thing is letting you type.)
• The “Already shaping what’s next” is a narratively unsatisfying section, as it promises stuff that you cannot see yet. Either show those, or skip the tease altogether.

I know the elephant in the room here is “how big companies do things.” A lot of redesign announcements and font unveils exist chiefly to make the execs who championed them happy, and perhaps as fodder for future promotion – I bet the whole “Already shaping what’s next” section isn’t really written for external audience – and they get chewed by the big PR machine that often files away whatever personality and quirkiness might have been there. Your job is to fight that machine! But I acknowledge that it might be hard.

However, I’ve also seen all this seeping into personal font announcements, which is unfortunate. (I don’t want to link to specific examples, since that’d be punching down.)

Also, this is not just about the joy of reading or some general notion of “craft” – although they are important, too. This is also purely informational. I feel I haven’t learned enough from the Geist Pixel announcement for the amount of time I spent with it. I don’t understand “multiple variants for different densities and use cases” or “semi-mono approach” or what stylistic sets are included. (My general goal is to write in a way that people can learn something new from any design announcement, even if they don’t have any prior context, and if they never actually use the font.)

It‘s a shame, because the work itself seems thoughtful and excellent, deserves a better intro, and could help others interested in typography as a jumping off point, particularly because this feels like a typeface off the beaten path.

Just to round up this post, some recent counterexamples:

• Fran Sans announcement post by Emily Sneddon (complements the font page) – personal, distinctive, talks about the process, shows interesting artifacts.
• I feel that every small essay from David Jonathan Ross’s Font Of The Month Club teaches me something new – pick a font you like on that page, then click Notes next to it.
• Departure Mono font page by Helena Zhang doesn’t use a lot of words, but still says a lot.
• Shantell Sans process post by Shantell Martin (complements the font page) – already talked about it before.

Andrew Gleeson designed Analog Mono, “fixing the crimes of VCR OSD Mono.” There used to be this classic pixel font that you’d see everywhere in the 1990s on hi-fi equipment: VCRs, TVs, camcorders, etc. One of its challenges was a low baseline which resulted in all the letters with descenders pulled up, for example:

Analog Mono fixes that problem:

Elsewhere, Kumiko Yoshida made Coral Pixels (also on Google Fonts), a color font that comes with the 1990s and 2000s colorful fringing baked in. The fringing was once an artifact of subpixel rendering, but now it is meant to evoke nostalgia or just as an interesting visual element in and of itself. (Perhaps adjacent to chromatic aberration?)

Lastly, here’s Two Slice by Joseph Fatula – a font that’s only 2 pixels tall, “and somewhat readable.”

Of course, these are all vector fonts – e.g. ready to be installed on a modern operating system – pretending to be pixel fonts. That’s maybe a separate post altogether, but it leads us to the last font, Geist Pixel from Vercel:

The copy introducing the font is a little pretentious/​spicy, but it touches upon something important:

Geist Pixel isn’t a novelty font. It’s a system extension. [… It] was designed with real usage in mind, not as a visual gimmick, but as a functional tool within a broader typographic system. […] This matters because pixel fonts often break in production. They don’t scale properly across viewports, their metrics conflict with existing typography, or they’re purely decorative. Geist Pixel was built to solve these problems, maintaining the visual texture teams want while preserving the typographic rigor products require.

There are definitely fonts whose Achilles’ heel is not the letterforms, but the invisible hard work put into everything that surrounds them: the kerning, the metadata, the extra glyphs, the vertical metrics. It seems that the team being Geist Pixel is proud of especially that last part.

The iOS 26 update introduced a bug in the Czech keyboard. Instead of the customary háček (ǍǎĚěǦǧǏǐǑǒǓǔY̌y̌) in the bottom row, another key was duplicated, removing access to the accent character (or, a diacritic) very popular in that language.

Here is the before and after of this situation:

Ordinarily, this can be frustrating but not insurmountable; you can always copy/​paste, rely on autocorrect to help out, or even add some topical text replacements for common phrases. The problem is that this bug only appeared on the keyboard used for logging on, and at least a few people used that character in their password. There, none of these workarounds were available – and so those people were now completely locked out of their iPhones.

The Register reported on this on April 12, and a few days later suggested that Apple was working on a fix. I won’t keep you in suspense; I just verified that the fix landed with the recent May 11 update.

This is, in an of itself, not a fascinating story, but with interesting things to talk about at its periphery.

First of all, The Register never showed a single screenshot. This led to a lot of confusion and speculation in the comments. Turns out, screenshots are valuable not just with bug reporting, but also with bug reporting.

Second, check out this Czech keyboard. Even within the limitations of the ancient QWERTY, there’s a lot of cool stuff happening here. Two new accented keys just appear on the top layer when you switch to Czech. Both have magical properties, too. They’re the modern “dead keys” that either stand alone, or get combined with the previous letter if that makes sense.

This is the stuff typewriters, and even desktop keyboards, could only dream of. But, as always, more software means more bugs, including some with unforeseen consequences; a typewriter could never break this way.

Thirdly, there is this interesting tension between us being led to believe “more interesting passwords are safer,” but then sometimes being penalized for actually making them interesting. A decade ago someone used emoji in their password without realizing they won’t be able to input it, and I’m sure there were other examples.

But the most interesting, to me, part? It’s the diacritic itself. Under one of the posts, a commenter wrote:

Stick with the 7-bit ASCII subset. You will never go wrong.

7-bit ASCII basically means “26 Western letters and nothing else.”

I hate this. I know it’s objectively true – in the late 1980s I felt a sense of relief my name didn’t have any of Polish language’s nine diacritics, which would complicate my life. Even just yesterday in Germany, I spotted this:

Software still struggles beyond ASCII. But this is why we need to keep pushing. Diacritical characters are to be found everywhere in the world. They’re detailed, and varied, and filled with histories. Umlaut is not diaeresis. Kreska is not the acute. A háček is not a breve. They’re rarely optional decoration, and often not even decoration at all; learning about Turkish dotless i might completely upend your understanding of what’s an accent and what is not.

If you don’t have a favourite diacritic, you are missing out. Even the names – grave! ogonek! horn! – are beautiful. (Háček is also known as caron and a wedge depending on context, and in other regions referred to with beautiful words kvačica and strešica.)

If you’re interested, here is David J. Ross’s 22-minute talk about getting to love diacritics from the perspective of a type designer. It’s filled with craft and playfulness:

My favourite accent is, obviously, ogonek. Just looking at Adam Twardoch’s guide on how it should be drawn fills my heart with joy:

Should you ever be worried that displaying just one glyph could take almost 2 seconds and slow down your website by as much? Naw, of course not. This wasn’t a problem already in the 1980s and, in the lord’s year 2026, computers are pretty good at rendering a letter or a symbol at a moment’s notice.

Ha. I was just messing with you. Of course you should alwaysbe worried about fonts. All the time. Typography is beautiful, but fonts are brutal. They will constantly put you to the test, they will find ways to get out of alignment faster than a Zastava Yugo, and they will teach you about corner cases in places you didn’t even realize had edges.

Fonts will break your heart like it’s the month before the prom again, and again, and again.

Or, in Allen Pike’s case, break a heart somewhat literally. Pike wrote a nice quick story of the complexity of what needed to happen to show the heart emoji, and how under a very specific set of conditions – a certain browser, a certain emoji font, a certain emoji within that font – this led to an extreme slowdown.

What’s really interesting is that in order to fix it, Apple can either improve Safari or the font itself, and at the moment of writing, it wasn’t clear what was the right thing to do. (Oh, yeah. Fonts don’t just have bugs. Fonts have many kinds of bugs.)

Another interesting in-between-the-lines thing is that Apple’s emoji are perhaps the only survivor of the original skeuomorphic pre-iOS 7 era. Even today’s emoji party like 2008 never ended – still glossy, still textured, still bitmapped. I’m curious whether somewhere deep inside Apple, there exist exploratory designs for flat, vector versions of emoji that never saw the light of day.

A 19-minute video from Tantacrul about a parallel universe that’s right next to ours, but most of us don’t get to think about – typography of fonts for music notation:

The video has some nice things going on besides specific details and conventions: there is a glimps of an obsolete app with a fascinatingly obtuse interface, a mention of modern standardization developments, and even a little (sad?) story of perfectionism and legacy.

I’m also kind of mesmerized by this shot of what music typesetting used to be:

There is also a short 1936 video showing more of that process. And small contribution from my end – a photo of the Keaton Music Typewriter from a museum in Catalonia:

Found in an archive of font design (for Olivetti typewriters) and smiled:

Handoff problems were there before us and will remain after we’re gone.

This, too:

From 2010 to 2021, Justin O’Beirne had been writing about online cartography, specifically in Google Maps and Apple Maps.

While both of these services changed a lot since the essays, they are still worth reading. They might be the closest to modern reviews of software as I can think of, and the way the essays are done also teaches us storytelling lessons – from nice visualizations and comparisons, to rich footnotes. There is also a great balance of high-level overview, and then jumping into specifics that reinforce it.

Here’s one example of cool tooling O’Beirne used to make his points more sticky:

I wrote a script that takes monthly screenshots of Google and Apple Maps. And thirteen months later, we now have a year’s worth of images:

The result is informative and mesmerizing:

Among the essays, I’d particularly recommend these:

• The back-and-forth of Google Maps’s Moat and New Apple Maps: Reverse engineering areas of interest, thinking of how the slow changes in visuals lead up to strategy, good visual comparison of competition, and small fascinating anecdotes of places like Parkfield, California. (And a great example of the old adage: don’t get into the business of predicting the future as this will age your writing the most.)
• A Year Of Google Maps & Apple Maps: Evolution and redesign as ways to “increase capacity.”
• Google Maps & Label Readability: A fascinating discovery of “city donuts.”
• What Happens to Google Maps? How cross-device compatibility can mess up maps.

There are also book recommendations and a memorable user story.

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)