As the name might suggest, Stop Stealing Sheep & Find Out How Type Works takes a breezy, irreverent approach to introducing typography to the lay reader. It does a good job of explaining the vocabulary of the field. It demonstrates how elements of of a typeface contribute to legibility in various contexts. And it introduces the fundamental concept of maintaining balance between line length, kerning, and leading. It explores a wide range of text applications — books, advertising, memos, etc. — with several examples of fonts and layout approaches that might be appropriate for each. (Although the book is published by Adobe, fonts from other type foundries are mentioned as well.)
It doesn’t go deep. It mentions typeface classifications like “Didone” and “Garalde” without exploring the distinctions. The authors frequently discuss the mood or tone of a group of typefaces but rarely discuss the elements of the font that establish the tone; when listing similar fonts they seldom explicitly discuss the differences between them.
Although I read the second edition, updated in 2002, the section on web typography is, perhaps inevitably, dangerously out of date.
Overall this was substantially more useful than Never Use More Than Two Different Typefaces. It should help an amateur do a less amateurish job of laying out type; and it should enable a design professional without a solid typography background to talk with one who does.