This great article at The Awl tracks "The Rise and Fall of Grunge Typography," bringing with it a sweet hit of nostalgia for the 1990s. In the 90s, grunge fonts reigned supreme. It was the same factor that drove grunge music: that sense that the uglier and dirtier something was, the more authentic it was. Sort of a garage band, "power to the people" kind of movement.
Dirty typewriter fonts said "real writing" the way that Verdana simply could not.
Grunge fonts were everywhere in the 90s, and I think there is another factor that drove this trend: people were getting increasingly uncomfortable with the transition to digital. I know that I, along with a lot of other people, specifically chose a dirty typewriter font because I felt like it hearkened back to the roots of real writing.
Something about the rise of the internet made me, in some way, yearn for the experience of reading letters that had been literally struck upon paper with an inky bit of metal shaped like a letter. By this logic, dirty typewriter fonts said "real writing" the way that Verdana simply could not.
It helped that The X-Files used a dirty typewriter font for its logo, thus adding the imprimatur of cool pop culture.
Dirty fonts were deliberately so, the way that people were also taking MP3s and adding "warmth" to them. You could add a whole bevy of clicks, pops, and hiss to a digital file to make it sound just like a record. There are still people who will argue that a record simply sounds better. They are probably right. But it's like arguing that riding a horse is better than driving a car. It may be true, but it is just not going to happen. How is a person supposed to carry a record player with them when they go jogging?
Distressing a font made it seem more real, as if it had been painted by hand, or photocopied a billion times. It made a thing created inside the computer seem aged and weathered, gave it that personal touch. It also made things look deliberately amateur in a very studied fashion. Amateur was cool: it was (there's that word again) authentic. It was zines and hand-written signs tacked up against light posts, and the punk revolution and all.
Many grunge fonts also referenced street art, stencils and spray paint and the rise of urban culture. This too was very carefully designed to look amateurish and messy, as if the cops were on their way so you had to finish spray painting your album art before they got here.
Ah the '90s; I wonder what horrible font fashions the future will bring?