This article uses two groups of case-study episodes to explore the complexities and perplexities that arise from the long-running use of a ‘floating timeline’ within The Simpsons. First, the conflicting representations of the youths of Homer and Marge in two ‘flashback’ episodes (‘The Way We Was’ and ‘That 90’s [sic] Show’) are examined. The logical quandaries presented by departing from a floating timeline and introducing fixed (but multiple and contradictory) historical reference points in individual episodes are outlined, and it is suggested that it may be better to accept the fictional paradoxes created rather than to try to resolve them. Second, the episodes featuring ‘Sideshow Bob’ are surveyed, and Bob is offered as being granted the unusual capacity (within The Simpsons’ fictional universe) to experience the passage of time and accumulate and retain an eventful history. This is contrasted with the temporal experiences of the Simpsons themselves, for whom there is eventfulness without progression. The article concludes by suggesting that The Simpsons’ status as an animated programme allows it to exhibit in a particularly pure and sustained form some of the relationship to time, history and the everyday of situation comedy and television more broadly.