So you’ve probably seen this around:

I’ve been wondering where the smiley came from for a while now (keeps me up most nights), and over the last couple days today I’ve done some digging to find out its history. As :awesome: is part of the emoticon set for the f13 forums, I began by asking schild, f13 founder.

driph: so whats the story of the gigantic smiley anyway?
schild: some guy on something awful made it
schild: some guy on 4chan made it BIGGER
schild: some guy on neogaf made it small
schild: schild made a tiny set of smilies out of them.
schild: fin.

That gave me a place to start, and further searching on the f13 boards led to this post by Fabricated, referring to the use of the smiley by Yahtzee in the most recent Zero Punctuation:

Um no.

That smiley originated from a Cyanide and Happiness comic, and became a smiley on Something Awful’s forums long before it was beaten to death here. He’s a goon.

Ah ha, Cyanide and Happiness! I was getting closer, and a random pumpkin carving blog entry led me to the particular comic referenced:

So, the source was found, or so I’d thought.

This epic thread on Something Awful from January of 2007, over a month before the comic went up, shows the escalation of the icon already well underway.

Originally purchased and added to the Something Awful smiley roster (SA has a pay system allowing members to add smileys) just prior to the above linked thread, it took off like a rocket. Known as :awesome:, the emoticon eventually reappeared as :fuckyou: and later :iamafag: after excessive overuse within GBS and other areas of Something Awful. This explosion of popularity led to its migration onto other forums, most notably 4chan (especially within /v/), where it was embraced with great vigor and enthusiasm.

*** Interstitial! A couple more web comics that have been erroneously linked as the source at one time or another.

After learning that the original purchaser of the smiley on SA was a user named Whalley, my next step was to get in touch with him. Finding Whalley wasn’t too difficult, and we chatted for a bit about :awesome:. Still amused at how widespread the whole thing has become, Whalley told me about its genesis:

driph: you originally bought that one on SA, right?
whalley: that i did
driph: was it a BYOB invention, or did you find it somewhere else?
whalley: much to my dismay of what i started
driph: I’ve heard everything from 4chan to SA to newgrounds, etc etc
whalley: some guy in byob drew it for this tiny little offsite forum he was at
whalley: i can’t remember who it was, i haven’t looked at an internet forum for like two months
whalley: he posted it one day though and i went “THAT IS SO AWESOME”
driph: nice.
whalley: and well now it’s the mascot for 4chan and has infected the entire internet
driph: the internet is a weird place.
whalley: i have come to be afraid of it

There you have it. Even with potential loose ends to tie up (who the artist was and the site he’d originally drawn it for), this wraps things up enough for me. schild was right, :awesome: did originate at SA, and while it was enormously popular there for a while, it wasn’t until its spread to 4chan that things really went nuts. Peaking in popularity in mid to late 2007, the reign of :awesome: has not yet ended. Spend any amount of time in /v/ on 4chan and you’re bound to see it pop up, and with its continued spread across forums and exposure to new audiences, :awesome: is here to stay.

An update!

Yes, as sleuthed by folks in the comments, the icon (and several other expressions) was indeed originally drawn for Pokemopolis. I recently corresponded with the creator of the smiley, and with her permission, here’s the story of the genesis, in her words:

I drew the icon years ago as part of an emoticon set he wanted for their new forum software, and I think he showed you all the other ones that were designed along with it. I’m not really sure what exactly I wanted it to represent but I think the ‘ridiculous childish glee’ that it now signifies is probably close!

I’m also a member at Something Awful and the first time I saw it posted I did a double take… I even remember my mind racing as to why and HOW someone had picked up a crappy lil’ icon off a tiny website, and I’m still not sure to this day… I assume a Pokemopolis member posted it on 4Chan. At that point I thought its posting would be a one time thing, but then I saw it more and more. It got to the point where I couldn’t read SA because everytime I saw it I’d just be completely freaked out, and naturally I came to hate it! I hoped every day that it would become bannable to post it, but the next best thing was replacing the VBCode. I also posted in BYOB in a thread Whalley made saying that I had made the icon originally, trying to get him to divulge where *he* had gotten it from. Most of SA assumed it was a ‘BYOB thing’ which was probably good because they’d probably want to lynch me if they actually knew where it was from.

I never expected it to become such a widespread meme, and I can’t say I even understand why its popular or why people want to make bag pins of it (Sure wish I could get some commission for the design though haha). It still weirds me out when I see webcomics use it though I’ve grown used to it now, sometimes I even tell nerdy neckbeard types that my dirty secret is *psst I drew THAT smiley*, which makes them say “MOAR!” or whatever is cool on 4Chan this week.

Though just for clarity sake my excuse for being on a Pokemon site in the first place was that I was young and stupid. But that’s the price of Internet fame!

So there ya go, mystery solved.