“Twenty years ago, I made the best font in the world,” declared Vincent Connare to a packed audience at Wired’s annual conference in London.

Not everyone will agree with that assertion, of course, when they learn that the font Connare’s referring to is Comic Sans. However, one detects that Connare’s tongue was planted firmly in his cheek when he made that on-stage boast.

For many, Comic Sans is the laughingstock of the typography world. For others, it’s simply another font that has its (niche) place in the design world. But to understand where Comic Sans is at, it may help to know how it came to be.

Comic Sans Font

Above: Comic Sans Font

Image Credit: Paul Sawers / VentureBeat

After working as a senior CAD designer at Agfa for some six years, Connare joined Microsoft as a program manager in 1993, around the time the Seattle-based software company was gearing up to launch Windows 95. “Everybody in the company was working on this program,” said Connare. “It was the biggest launch in the history of computing at that time. I’m privileged to have been part of that time in computer history — it was very exciting to be at the beginning of consumer software.”

AI Weekly

The must-read newsletter for AI and Big Data industry written by Khari Johnson, Kyle Wiggers, and Seth Colaner.

Included with VentureBeat Insider and VentureBeat VIP memberships.

Connare says that when he first joined Microsoft, there was a strong entrepreneurial spirit in the company. “They told us that you were the best in the world at what you do,” he said. “So, if you aren’t supposed to wait for your boss to tell you what to do, you tell your boss what you want to do. And that was key. Everyone was thinking what is the best thing to do now, and not listening to the boss if they (the boss) were trying to tell them what they thought the next big thing was. Everyone was entrepreneurial, and everyone was thinking in those terms.”

Microsoft Bob

Above: Microsoft Bob

Image Credit: Wikimedia Commons

It’s not clear whether that had a direct influence on the emergence of Comic Sans, but it surely played a role. In the early days, Microsoft used to create a lot of consumer programs, such as Creative Writer, which was kind of like an early version of Microsoft Word for kids, featuring fonts, effects, clip art, and so on. But then one day, one of Microsoft’s program managers arrived in the office with a new piece of software called Utopia, which later became Microsoft Bob — a sort of more user-friendly version of the Windows operating system.

Microsoft Bob itself wasn’t well received, and over the years it has cropped up in various worst product lists. But that’s irrelevant to this story.

Connare was asked what he thought of the fonts. “I saw this dog, talking in Times New Roman, and I just thought, ‘That’s wrong’,” he said. “I like comics, I have comic books, and they don’t talk in Times New Roman. I looked at a few (comic books), and realized that most comic books (fonts) are hand-done.”

It turns out that the main inspiration for Comic Sans came from two comics — The Dark Knight Returns and Watchmen. “Watchmen was the closest one to a typeface, so I looked at it and just slowly, with a mouse on a computer, drew letters one at a time, trying to get the weight about right,” explained Connare.

Watchmen

Above: Watchmen

“It didn’t have to be perfect,” he continued. “I would do it over and over and over again, until I got something that resembled, but wasn’t copying, Dave Gibbons‘ lettering from the comic book. I wanted to make it … different. I wanted it to look like handwriting.”

As things transpired, Comic Sans didn’t actually make it into Microsoft Bob — but it did make it into 3D Movie Maker, which was similar to Microsoft Bob insofar as you had cartoon characters you could move around and do things with. The font then made it into Microsoft Comic Chat, which was similar to AOL chat, in that you could type messages to others on the Internet.

Comic Chat

Comic Sans later made it into Windows 95 before becoming one of the main default fonts in Internet Explorer and Microsoft Publisher, not to mention Apple’s OS X.

The font has achieved almost cult-like status in recent times — generally mocked, but in a sort of loving way. Connare and his font have been covered by big-name Western media brands, as well as local publications such as Esquire in Russia. But despite the nay-sayers, Comic Sans refuses to go away.

In Spain, authorities engrave the Copa del Rey soccer trophy in Comic Sans. In 2013, the Vatican commemorated the Pope with a photo album that sported descriptions in Comic Sans. And a year earlier, minor outrage spilled onto Twitter when CERN presented some of its finding around the Higgs boson particle in Comic Sans. “The question I get often is, when is a good time to use it [Comic Sans],” said Connare. “You have a science experiment where CERN was tweeting worldwide when they discovered the Higgs Boson, and using Comic Sans didn’t hurt them. I think it made them trend [on Twitter] even further.”

Connare left Microsoft in 1999, and today lives in London, England, where he works as a technical evangelist for font foundry Dalton Maag.

VentureBeat's mission is to be a digital town square for technical decision-makers to gain knowledge about transformative enterprise technology and transact. Learn More