Nate Piekos, comic book letterer supreme, explains how he created the typeface for Francesco Francavilla’s wonderful Black Beetle series at Dark Horse:
I got to work right away on the font that would eventually become Blambot’s Tough as Nails BB. Since I try to come up with two new fonts every month, I was killing two birds with one stone—the perfect font for The Black Beetle’s dialogue and a new font for public release.
I remember making one solid pass at a finished design, showing it to Jim, and taking a day or so away from it. When I came back with fresh eyes, I realized the “pen style” was wrong.
The letterforms worked, but instead of a uniform Rapidograph style, the font would be even better if I made it look as if it was lettered with a calligraphy tip. To go one step further, I reversed the angle that most comic hand letterers hold their pens at so that the vertical strokes were thicker than the horizontal. This is not a matter of pushing a few buttons in AI; it meant reworking each letter individually. Meanwhile, the clock was ticking and I had to start lettering the pages coming in!
If you’re a process wonk like I am, this kind of thing is fascinating.