I'm not sure there's a bad issue of Ice Cream Man at all, but the ones collected in Volume 8 are among the best. A couple of nicely creepy ones, but even then, Chapter 29 is a rather lovely presentation of the living will of our Will Parsons, rather badly treated by Riccardus in an earlier issue.
But it's 31 & 32 that are the gems. Chapter 31, titled "A Scale (Sort of a Poem)" is a beautifully symmetrical telling of a life's connections (and failed connections), of intergenerational love, and the artistry of the telling makes it all the more touching. While Riccardus the Ice Cream Man does feature, this story, along with Chapters 29 and 32, is grounded in his brother & opposite Caleb's axioms that "everything is one thing". The interconnectedness is demonstrated within the story - the fishing and the caring for fish comes to mind - but this chapter is one of the most intertextual within the Ice Cream Man canon too, with numerous callbacks to other chapters.
And that's another clever thing about this story: the contradictions. It's beautifully self-contained, mirroring itself all the way through to the "Oh my God" on the first and last pages, but it's so intertwined with the rest of Ice Cream Man that practically everything is a reference. It's a story about connection and love, but it's about two loners. And heck, it's a heartfelt, sincere story built from the elements of creepy, often nihilistic material.
And if that intertextuality is the only thing that would make me hesitate to show Chapter 31 to friends who don't know, or wouldn't care for, Ice Cream Man, Chapter 32 does a similar trick, but is perhaps even more self-contained. In fact it's the one issue of Ice Cream Man I bought separately, after reading a few pages in the comics store. It's a story of a guy going into rehab and... getting better. When I found it on the shelf it felt very much unexpected, and is probably what prompted me to take the series seriously and get caught up on the collections.
Oh, and if you need clarification about the intertextuality, the intro to Chapter 32 makes it all very explicit, semiotically... including a sweet reference to the Covid pandemic that was in full swing when it was created. There's also a pretty big reference in there, that Doug is, but also isn't, the author - because our Billy Prince just can't help himself, right?
There's nothing new under the sun, but with Ice Cream Man I do think W. Maxwell Prince, along with the sterling artist Martín Morazzo and excellent colorist Chris O'Halloran, has created something rare, rich and unexpectedly different with this anthology.