My purpose here in this article is to sketch an answer to the following question: what did Nietzsche mean when he wrote in Ecce Homo that his books attain here and there “the highest thing that can be attained on earth—Cynicism” (EH Why I Write Such Good Books §3)? At first glance, the idea that ancient Cynicism might be invoked here seems implausible. Were not the dogs, or Cynics, of antiquity the bluntest, crudest, least learned of the ancient schools of philosophy—assuming they can be called a philosophical school, which was doubted even in antiquity? And what survives of the Cynic classics of the fourth and third centuries BCE, aside from a few fragments of Crates and the scurrilous anecdotal traditions preserved in Book 6 of Diogenes Laertius's gossipy Lives and Opinions of Famous Philosophers? What could be here that Nietzsche could sink his canines into? Fortunately (for me), the case for the importance of the Cynics for Nietzsche on every level from literary style to philosophical stance has already been brilliantly made by Heinrich Niehues-Pröbsting. I would like to revisit that case here with a view to supplementing and extending some of its key points by looking at Nietzsche through a Cynic lens, as well as at Cynicism through Nietzsche.