It’s hard to disagree that virtual assistants have wrought little good in this world. From Clippy’s benignly stupid questions to BonziBuddy’s spyware and evil homepage resets, it’s a wonder that Siri or Google Now have been able to reclaim any goodwill. But it turns out that virtual assistants have a more lasting negative impact than general annoyance: the font Comic Sans.

Comic Sans lore says that Vincent Connare, a designer on a Microsoft consumer software team, saw a working prototype of the assistant Microsoft Bob back in 1994. This featured a cartoon dog named Rover speaking in text bubbles and, incongruously for a cartoon, Rover spoke in Times New Roman.

In what can now only be described as dramatic irony, Connare was shocked and appalled at how ugly Times New Roman looked coming out of a cartoon’s mouth. He decided that a more comic-like typeface was needed.

Connare has made clear in the past that he drew inspiration for Comic Sans from no less than Alan Moore’s Watchmen and Frank Miller’s Batman: The Dark Knight Returns. But according to an interview with fonts.com, Comic Sans was developed with the express intent of shipping with and for Microsoft Bob.

Comic Sans was not just inspired by Bob. Comic Sans was because of Bob. This is like learning ShamWow Vince was the progeny of Billy Mays.

Connare was not able to perfect the font by the time Windows 95 and NT shipped with Bob, which was intended to be a friendly replacement for the Program Manager. In August 1995, Comic Sans shipped in the Windows 95 Plus Pack, began being included in OEM versions of Windows 95, and was also used in 3D Movie Maker, according to Connare.

Bob was set up like a virtual house toured by Rover, where clicking on things allowed you to complete essential functions like opening programs or adding a retro chair to the home’s decor. The interface was universally hated and gone by the time Windows 98 rolled around. Some functionality, like displaying essential letter-writing tips over a document, lived on in the form of Clippy.

Comic Sans and Bob were never married the way Microsoft intended, but Comic Sans needed no introduction. To flyer-creators, PowerPoint makers, and website designers mulling through their choices in the font selection pane, it shone and throbbed like a big fat nonthreatening beacon in the night. It was borne to fame by its mediocrity, the "Achy Breaky Heart" of typefaces. Now it facilitates reading comprehension, the sharing of feelings, and unbridled Internet anger.

It’s hard not to think of Comic Sans as the most popular typeface that almost never happened, if only someone at Microsoft had the foresight to can Bob before anyone could see it. Steve Ballmer’s own hindsight assessment of Bob: “We have decided that we have not succeeded and let's stop.” If he’d stepped in, humanity could have avoided this unsightly digression from Times New Roman and transitioned smoothly into Helvetica. Comic books could preserve some of their dignity and we, in all probability, would have avoided the Brush font in the iOS notes app.