Just click here for a batch of Milton Glaser essays. "Since Then" is a talk and feels like a talk and so isn't an exemplary piece of rhetoric. It is also a bit dated (think post-2004 election and not beyond), but Glaser does raise the issue of artist / (or vs.) designer. "Ambiguity and Truth" raises questions regarding the ethics of design. "Dark and Light: The Strange Case of the Decline of Illustration" of course talks about... the decline of illustration, but also looks at root causes, like the influence of media, particularly television. Please note that all of these essays are available in PDF format and so with some patience and wrangling can be easily linked to on Go Studio.
I've found that Glaser is helpful for starting discussions and raising issues. Because the arrangement of his essays / talks can be somewhat sloppy, students sometimes try to respond to incongruous parts of the essays, and often struggle to write cohesive responses. I always make sure that if a student plans to respond to Glaser that she does so in a pointed way and that she carefully frames the debate. Go to Glaser for engaging and sometimes controversial ideas, but not for exemplary organization. (I should add that he is a good example of a writer/rhetor who is able to use autobiography in the persuasive realm.)