The Secret Ska History of That Weird Levitating Businessman Emoji

The site emojitracker, before it was announced that it was shutting down earlier this month, documented the real-time usage of emoji. It featured a massive spreadsheet of the icons, and every time an emoji was used on Twitter, its box would light up. It was a fascinating document of public moods. Toward the top, the most popular expressions—crying with laughter, kissy face, heart eyes—flared up multiple times per second. Toward the bottom, the least popular icons, mostly outdated tech like floppy discs and pagers, lit up every couple of minutes.

Missing entirely from the list was perhaps the most enigmatic emoji of all:

What is that for? It's one of the least popular emojis (ranked 1233 of 1679 on Twitter), perhaps because nobody is really sure what it is or how to use it. There aren't many hints. It's filed under the "activity" section on iOS, and its description, when rolling over the icon in iMessage—"Man in business suit levitating" (MIBSL)—isn't exactly helpful. Fusion called him "confusing" and the Paris Review's blog described him as the eerie "floating face of capitalism."

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As it turns out, there's a pretty strange history behind the icon involving ska music, Peter Tosh and the guy who created Comic Sans.

MIBSL was born in the late '90s, while Microsoft was working on Internet Explorer 4.0. The browser featured a new symbol font called Webdings, a sort of web-optimized version of Wingdings. For those who didn't use a computer in the '90s, Wingdings swapped letters on your keyboard for little black-and-white images, kind of like emoji but way more difficult to use and way less socially acceptable. (And yet somehow it was cool to use as many campy gifs as possible. It was a strange time.)

Webdings included 230 images, culled from when Microsoft's "team of iconographers traveled the world asking site designers and users which symbols, icons and pictograms they thought would be most appropriate for a font of this kind." This included useful things like a disembodied eye and a smiling pirate inside a "no" symbol (likely for offices prone to vicious pirate attacks). There was also this guy, set to the letter "m." Look familiar?

That suave looking levitating man was created by Vincent Connare, who was working in the Microsoft typography department at the time. He's perhaps most infamous for designing the much-derided font Comic Sans. When I spoke to him, he was slightly wistful about his time at the company, describing it like being in college. His office was near beach volleyball courts and a softball field. "We played a lot of volleyball," he said.

After deciding to incorporate Webdings in the browser, the Internet Explorer team and Connare's manager, Simon Daniels, drew up a list of symbols to design, mostly stuff that might look good on a website in 1997. Connare went down the list, selecting the ones he was interested in. One option immediately stood out.

"I had a Specials Japanese import LP, and I saw one of the keywords was 'jump' so thought it would be good to make a jumping, pogoing man," he said. "The style of the 2 Tone guy was black on white, and it was graphic, so it was easy to make something like it into a font."

For those who never went through an awkward ska music phase as a teenager (pickitup, pickitup, pickitup!), 2 Tone Records was a label formed in 1979 by The Specials keyboard player and songwriter Jerry Dammers. Their logo depicts a man dressed in the rude boy style of the British ska revival, complete with sunglasses, a black suit and a porkpie hat. Dammers loosely based it on a photo of reggae musician Peter Tosh, from the cover of the Wailers' 1965 album The Wailing Wailers, and named him Walt Jabsco, a name he lifted from an old T-shirt.

This wasn't the only musical reference hidden in Webdings. "There is also an Aladdin Sane Ziggy bolt in there, and a Shure 55 mic," Connare said. "The keyboard is a MIDI keyboard based on an old Sequential Circuits Pro One and Kawai K4 that I owned in the '80s and '90s."

Additionally—and partially as a response to an odd conspiracy theory claiming that Wingdings included secret anti-Semitic messages that spread via email in the early '90s (and again after 9/11)—he inserted his own little Easter egg in the font. "I made NYC equal 'eye heart city' or 'I love New York,'" he said.

Seventeen years later, in 2014, the Unicode Consortium—the nonprofit organization that manages the Unicode standard and determines, among other things, which emoji get approved—announced that Version 7.0 would add a bunch of new icons. Most of the new additions were adaptations of Wingdings and Webdings characters and, thus, the jumping rude boy became the levitating businessman, receiving the official Unicode designation U+1F574. (Weirdly, there's still no option to change the character's skin tone, even though he was based on the image of a black man. Hmm.)

But long, circuitous story short: The levitating businessman emoji was based on a Webdings character, which was based on the logo for a '70s ska punk record company mascot which was based on a photo of Tosh. Whew. Ska music lives on—in emoji form.

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