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.
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.