Comic depictions of Adolf Hitler are not a new phenomenon as examples of the Führer’s mockeries are observed in the early 1940s, especially in anti-Nazi propaganda films like Charlie Chaplin’s Great Dictator. The most troubling fact, three quarters of a century after the end of World War II, is the frivolous and decontextualized treatment aroused by the Nazi tyrant. To demonstrate this, we chose to analyze two recent novels – Timur Vermes’ Look Who’s Back and François Saintonge’s Dolfi and Marilyn – , which help reflect on key issues emerging from this particular form of black humour. Laughing at or about Hitler not only brings us to the limits of social acceptability with regards to humour, but also tests our lucidity toward the risk of history repeating itself.