Imagine spending like a quarter of a million
dollars, $237 ,500 to be exact, on a digital
receipt for a colon, a hyphen, and a bracket.
I mean, it sounds completely absurd on its face.
A literal fortune spent on just three standard
punctuation marks. Right. But that transaction
actually happened back in 2021. And what that
buyer was really paying for wasn't just like
punctuation, they were buying the documented
origin point of a global language. Yeah, they
bought the exact moment humanity figured out
how to inject its tone of voice into a machine,
which is it's a huge deal. It really is. And
it's the ultimate solution to a problem that
has plagued written communication for as long
as we've been writing. Like how do you convey
sarcasm or genuine sympathy or pure joy when
all you have is this rigid text only framework.
Exactly. The words are there, sure, but the music
of the conversation is completely missing. And
that missing music is exactly the focus of our
deep dive today. We are pulling from a really
comprehensive, incredibly detailed source, the
foundational Wikipedia article on the emoticon.
Which, just to define it officially right up
front, is a portmanteau of emotion and icon.
It's a pictorial representation of facial expressions
using regular characters, you know, like punctuation,
numbers, and letters to convey non -verbal cues.
Okay, let's unpack this because our mission today
is to explore the surprisingly centuries -old
history. the cultural variations, and the high
-stakes economy of these little faces. Yeah,
because every time you type a simple smiley face
on your phone, you are actually participating
in a lineage of human expression that goes back
way, way further than the internet. Way further,
right. Like, before we even get to computer screens,
we have to look at how people try to solve this
tone problem in print. Right. If you look at
the historical footprint, the earliest potential
sighting in our sources is actually from the
year 1648. Wow, 1648. Yeah, a poet named Robert
wrote a line of verse that ends with the phrase,
smiling yet, followed by a colon and a close
parenthesis. Wait, so a literal sideways smiley
face sitting right there in a 17th century poem?
Well... We do have to be a bit careful with intent
here. English professors like Alan Jacobs point
out that 17th century typography was notoriously
messy. Just kind of all over the place. Exactly.
Printers often just threw colons and semicolons
inside brackets as a matter of standard, albeit
chaotic, practice. So the consensus leans toward
it not being a deliberate face. Right. But even
if it was just a typesetting accident, I mean,
it highlights how long those specific shapes
have been hiding in our literature. Definitely.
And that ambiguity in print is exactly what forced
people to develop actual deliberate systems once
we hit the telegraph era. Like I was reading
about the telegraph operators in 1857, and this
completely shifted my perspective. Oh, the numeric
codes. Yeah, that's a fascinating era. Yeah.
They were using Morse code numbers to convey
tone and affection quickly. They used the number
73 to mean love and kisses. which eventually
evolved into best regards. And they used 88 for
a similar sign -off. And the mechanics of the
telegraph explain exactly why they did that.
Because telegraph communication was charged by
the word or the letter. Right, it wasn't cheap.
Not at all. And physically tapping out a message
was a slow, mechanical effort. Bandwidth was
incredibly expensive. So tapping out 73 is vastly
more efficient than transmitting, I am sending
you my warmest affections. It's basically the
19th century version of LO. You're just optimizing
for speed. Exactly. But people were still subconsciously
hunting for a visual solution, not just a numerical
code. Like in 1862, a typist transcribing a speech
by Abraham Lincoln noted the crowd's reaction.
Oh, right. I saw this in the sources. Yeah. In
the middle of the text, it says, quote, applause
and laughter, end quote. Semicolon, close parenthesis.
A winking face. But is that one real? or another
accident. Linguist Philip Surgeon argues that
one was just a pure typo, just a slip of the
finger on the typewriter. OK, but by 1881, it
definitely wasn't a typo anymore. Puck Magazine
published what they called typographical art.
Right. They explicitly laid out sequences of
punctuation marks to show joy, melancholy, indifference,
and astonishment. They were literally pointing
at the typewriter and showing the public, like,
look at what else these keys can do. And that
idea caught the attention of some brilliant literary
minds who recognized that the typewriter was,
well, emotionally bankrupt. In 1912, the satirist
Ambrose Bierce suggested using a curved horizontal
line. Like a little smile. Yeah, to represent
what he called cackination, or loud laughter.
And later, in 1969, Vladimir Nabokov told the
New York Times that he desperately wanted a supine
round bracket to represent a smile in text. I
just, I look at Nabokov wishing for a smile punctuation
mark like a sci -fi author predicting the smartphone.
He knew exactly what society needed. decades
before the technology actually existed to make
it a daily standard. He saw the gap, but he was
just dreaming. Because the problem of tone couldn't
actually be solved until technology forced our
hand. Which happened disastrously in 1982. Yeah,
that brings us from the desire for emotional
texts to an absolute urgent necessity. Because
when early computer networks came online, they
stripped all vocal tone, all body language, and
all facial expressions from real -time communication.
And it didn't just cause awkwardness. No, it
caused genuine panic. The mercury spill. This
is the exact moment the conceptual became practical.
So the year is 1982. We are at Carnegie Mellon
University. Researchers are communicating on
an early digital bulletin board system, a BBS,
and someone posts a sarcastic joke about a mercury
spill in a university elevator. Think about the
mechanics of a BBS in 1982. You are looking at
a text only black and white or green and black
monitor. There is no formatting. There are no
images. Nothing to give it away. Exactly. A joke
about a lethal chemical spill looks fundamentally
identical to an official safety warning about
a lethal chemical spill. The readers had zero
context clues. So computer scientist Scott Fallman
steps in. He proposes a protocol to stop the
panic. He posts a message suggesting that users
type a colon, a hyphen, and a right bracket to
label attempted humor. And a colon, hyphen, left
bracket for serious messages. Right. And it's
spread with astonishing speed. across the ARPANET
and USENET. And to understand why it caught on
so fast, you really have to look at the culture
of those networks. ARPAN was heavily populated
by universities and the military. So, very structured
environments. Extremely. It was a high -density
environment of engineers and scientists who relied
entirely on standard protocols. Fallman essentially
handed them a simple, elegant protocol for human
emotion. But our sources mentioned that Fallman's
design wasn't actually the only one proposed.
People were actively trying to solve this problem
with different symbols, right? Yeah. Somebody
suggested using an asterisk and an ampersand,
with the ampersand supposed to represent a person
doubled over in laughter. Which is so complicated.
It is. Others suggested a percent sign or a pound
sign, but those alternative designs died out
almost instantly. Fallman's won decisively. And
I think there is a clear cognitive reason for
that. I was thinking about why the colon and
the brackets stuck while the ampersand vanished.
Has to be periodotly right. Oh, the psychological
phenomenon of seeing faces in random objects.
Exactly. The human brain is hard -wired to look
for faces in everything. Clouds, toast, the front
grill of a car. The sideways face is an instant,
universally recognizable pattern. That makes
perfect sense. Right. If you send me an ampersand,
I have to do... like cognitive work to remember
that it's supposed to be guy laughing. But a
colon and a bracket bypasses my intellect and
hits the face recognition center of my brain
immediately. Exactly. It was the most cognitively
elegant solution available on a standard keyboard.
And once that foundation was laid, the timeline
really accelerates. Because users realized they
didn't just have to use Falman's two faces. Right.
The shapes naturally evolved. emoticons stopped
being a rigid safety protocol and started functioning
exactly like spoken slang. You get the semicolon
for the wink. Yeah. The colon and the capital
P for sticking your tongue out. The XD for eyes
squinched shut in laughter. Even the less than
three for a heart. And as this visual slang expanded,
it underwent a subtle but highly significant
change. In 1996, the Smiley Company, run by Nicholas
Lufrani, launched the Smiley Dictionary to catalog
over 500 of these ASCII emoticons. their catalog
designs, they drop the hyphen. They removed the
nose. It went from colon hyphen bracket to just
colon bracket. Wait, so dropping the nose wasn't
just laziness or trying to save a single keystroke.
I mean, our sources note a researcher at Stanford
University actually analyzed four million tweets
and found that the noseless smiley is vastly
more common today than Fallman's original version
with the nose. It is vastly more common, yes.
Are you saying the missing hyphen was a deliberate
social signal? It absolutely is. Linguist Vivian
Evans attributes this shift to a concept called
covert prestige. Covert prestige? What does that
mean exactly? Covert prestige occurs when a specific
demographic, very often younger users, deliberately
rejects the standard formal or quote unquote
proper way of doing something. They do it to
demonstrate in -group membership. Oh wow, that
makes perfect sense. It's exactly like a teenager
saying gonna. instead of going to. Precisely.
If someone texts you a smiley face with a hyphen
for a nose today, it almost feels like they're
writing you a formal letter. Yeah, it feels like
it's from my boss. Right. By dropping the nose,
you are signaling to the reader that you are
fluent in the casual modern digital landscape.
You are actively rejecting the formality of the
original 1982 protocol. You're saying, I'm fast,
I'm part of the current culture? It's wild that
there is an immense amount of social data packed
into the absence of that tiny horizontal line.
It really is. But we should note that all of
that social data, all those sideways faces, were
entirely dictated by the physical layout of Western
keyboards. Oh, right. You had to tilt your head
because of the specific keys we had available.
Exactly. But as the internet spread globally,
that physical limitation disappeared for a lot
of users. leads to a massive geographical divergence.
Because languages with different, much larger
character sets didn't have to tilt their heads.
They have the type of graphic tools to build
faces that you read straight on. Exactly. This
is where the creativity just explodes. We get
to cow emoji. Right. Arising on ASCIInet in Japan
around 1986, cow emoji are essentially vertical
emoticons. Japanese characters are often double
bite and offer a vast variety of curves and shapes.
So users could construct detailed expressions
without the sideways perspective. Like the classic
awo or uwu. Yes. And it didn't stay isolated
to Japan. Users on the Japanese discussion board
to channel. And users in Korea started pulling
from entirely different alphabets to build these
faces. Like they grabbed Canada script from India
to make that highly specific look of disapproval.
The two circles with dots in the middle of the
underscore. Write the T to matter face. And Korean
users utilized hangul vowel jamos to depict crying
faces where the vertical and horizontal lines
perfectly mimic streams of tears. And in Chinese
internet culture. They took it a step further
and repurposed actual ideographic characters,
right? They did. They found characters where
the structural lines naturally formed a face.
The character meaning patterned window is completely
co -opted because it looks uncannily like an
open -mouthed, distressed face. Oh, I see that
one. Or the character, which is a variant of
the word for plum. Because it resembles two little
people standing side by side, it's used online
to represent a double magnitude of dullness.
They took it. Ancient scripts and turn them into
modern emotional avatars. It's incredible. Yeah,
but we have to talk about the legend of oars
or Z The sources highlight this is a prime example
of internet culture, but I need you to break
down exactly how this started. It's a great story.
It starts in late 2002 on a Japanese personal
website forum called TechSide. A user was trying
to ask a highly specific technical question about
a cable and its cover. Okay, a cable and a cover.
Yeah, and to illustrate what they were talking
about, they typed out a sequence of characters.
an underscore, a vertical pipe, a sort of roof
character, another vertical pipe, and a circle.
Okay, I'm trying to picture that in my head.
A pipe, a roof shape, another pipe, and a circle.
It just sounds like a drawing of a tiny house
next to a ball. That's how it started, a completely
mundane hardware diagram. But look at the circle
as a head. Oh, wait, the roof character is the
back, the pipe is the arms, it's a person on
their hands and knees. Exactly. Other users looked
at that sequence of characters and instantly
recognized a stick figure doing a Japanese dogeza
bow, which is like a person kneeling on the ground,
head bowed in deep despair or frustration or
profound respect. Right. And the internet's collaborative
imagination took over instantly. That visual
of the kneeling man was so resonant that the
community quickly simplified it into standard
Western letters to make it easier to type. O,
R, and Z. Ah, so the O is the head on the ground.
The R is the arms pushing up. And the Z is the
bent legs, oars. That is wild. They saw a guy
completely defeated by life. in the drawing of
a cable cover. And ores spawn an entire subculture.
There were blogs dedicated to it. It became a
ubiquitous shorthand for crushing psychological
frustration. I love how minimalist that is. Just
like O7, where the O is the head and the seven
is the arm saluting, it communicates instant
respect with two keystrokes. It proves that once
humans are given a medium, even a highly restrictive
one like a standard keyboard, they will inevitably
bend it toward emotional expression. But the
medium didn't stay restrictive for long. because
as technology evolved to support rich media moving
from text -based bulletin boards to mobile phones
and instant messaging, the simple punctuation
marks were given a graphic facelift. Right. We
call this the second generation, or portrait
emoticons. In 1997, Nicholas Lufrani, who we
mentioned earlier from the Smiley Company, took
those ASSI text designs and officially registered
them as graphical GIFs at the U .S. Copyright
Office. Oh, wow. So he actually legally registered
them. He did. He gave them color, added features
like little white hands and gloves and categorized
them. And the text strings morphed into visual
icons. This is really where the emoticon economy
takes off. Because suddenly these quirky workarounds
became highly valuable commodities and the tech
giants realize they needed to control this space.
Absolutely. Between 2007 and 2009, companies
like Google and Apple petitioned the Unicode
Technical Committee to standardize emojis globally.
Which is a huge deal, right? It is a critical
mechanical shift. Unicode is the universal standard
for how text is represented in computing. By
getting emojis into Unicode, Google and Apple
ensured that these graphical faces stopped being
a localized software quirk -like, a specific
font you had to download, and became fundamental
global infrastructure. It meant a smiling face
sent from an Apple device would be universally
understood by a Google device. Exactly. And once
it's infrastructure, it dominates. A 2024 BBC
report noted that two of the top three emojis
used globally are actually portrait emoticons
faces representing emotion. And the media landscape
capitalized on it, too. Like in 2004, the chat
application Trillion introduced Amo the blips,
which were streaming audio and video equivalents.
Right. And in 2007, MTV created Emote Eclipse
to market their show The Hills. Emote accounts
were no longer just text protocols. They were
multimedia assets. And where there are valuable
assets, intellectual property battles inevitably
follow. The legal stakes and the sources are
fascinating. They really are. Like in the year
2000, a company called Despair Inc. got a satirical
trademark for the frowny face. Then in 2008,
a Russian entrepreneur claimed he held the trademark
for the winking face. Oh, yeah. And he actually
threatened that companies would have to pay tens
of thousands of dollars for a license to use
it. But those attempts generally fail in the
courts. And the legal mechanism for why they
fail is really important. You cannot easily copyright
or trademark a universal linguistic standard.
Because it belongs to everyone at that point.
Exactly. Once a symbol like a winking face is
adopted by the general public for everyday communication,
it becomes utilitarian. It's a functional piece
of language. Trademark law is designed to protect
distinct brand identities, not to let one person
own the alphabet. Which brings us full circle
back to Scott Fallman and that $237 ,000 NFT.
Yeah. You can't own the punctuation itself, but
you can own the digital artifact of its inception.
Exactly. The buyer of that NFT purchased the
digital equivalent of the Rosetta Stone. They
secured the original 1982 BBS message. Man, when
you lay it out like that, it completely changes
how I look at my own keyboard. And for you listening,
as you go about your day, think about this the
next time you send a message. Every time you
are deciding between a simple, noseless smiley,
an enthusiastic XD, or dramatic orays because
you spilled your coffee, you are not just typing.
No, you're really not. You are participating
in a rich... centuries old lineage. You are part
of the continuum that stretches from telegraph
operators in the 1800s straight to a quarter
million dollar piece of digital history. And
that leaves us with a critical question to consider.
We've seen the human need for tone force emoticons
to evolve from Morse code to text to fully rendered
3D graphics and multimedia sounds. Right. So
as we move rapidly into an era of virtual reality
or even direct brain computer interfaces where
your exact emotional state theoretically be transmitted
instantly to another person? What happens to
the emoticon? Will the text -based smiley eventually
go extinct as a primitive relic of early computing?
Or is there something so fundamentally elegant
about the simplicity of a colon and a bracket
that we will always need it to convey our truest
selves? When all the complex graphics and immersive
tech fall away, maybe all we really want is to
see a human smile hiding in the punctuation.
Thanks for joining us on this deep dive. Stay
curious and we'll see you next time.