How do we understand Shakespeare’s invitation to laugh in the context of war? Previous critical accounts have offered too simple a view: that laughter undercuts military ideals. Instead, this article draws on the Aristotelian description of laughable ‘deformity’ and Plato’s description of laughable ignorance in order to characterize Shakespeare’s laughter in the context of war more carefully as an expression of ‘relative painlessness’. It discusses how the fraught amusement of Coriolanus (Coriolanus), the reciprocality of Falstaff and Hotspur as laughable military failures (1 Henry IV) and the laughter of Bertram at Paroles (All’s Well That Ends Well) each engage with an ancient philosophical conundrum articulated poignantly by St. Augustine: the requirement that a Christian civilization engage in war to defend itself against honour-obsessed aggressors without turning into a like aggressor itself. Shakespeare’s laughter at war enacts the desire for that balance.