Housing Benefit Hill was a series of columns which appeared in the Guardian Weekend between September 1993 and September 1996. Originally it featured a cartoon series by Steven Appleby, which were very funny, but not specifically intended as illustrations of the text. (Mind you, sometimes they could be accidentally appropriate). However in September 1995 the editors at the Guardian commissioned Ian Pollock to illustrate the stories, and the results are shown below.
They are remarkable drawings, not least because somehow or another Ian seemed to be able to capture not only the essence of the story, but the actual appearance of some of the characters. It was genuinely uncanny. I never met Ian, and, as far as I know, he never visited the people or places I was talking about, and yet, on the scantiest of information, he was able to do a portrait of that person of such accuracy it was as if they were sitting for him as a model.
You can see all the illustrations here.