An aggressively casual font

In October of 1994, a Microsoft designer named Vincent Connare saw a beta of Bob, and found the use of the staid Times New Roman typeface in its word balloons to be out of whack with the software’s playful personality. He began work on an aggressively casual font that wound up being dubbed Comic Sans; it didn’t make it into Bob, but was later bundled with Windows itself. Comic Sans ended up as the Microsoft Bob of typefaces: It’s famous mostly for being unloved.