What should we make of the glaring absence of the emperor Nero from Seneca’s Epistulae morales – not mentioned once in 124, often lengthy, letters, written by a man who had been for many years one of his closest associates? Although Seneca does sometimes allude to the question of how frank advice may be offered to the powerful, the letters barely touch on imperial politics, beyond advising their addressee that he would be better off withdrawing from the public sphere. Yet if Nero is not present explicitly, there are a number of respects in which Nero’s domination of others as well as his failure to exercise control over himself are constructed as implicit and potent anti-models in the letters. When Seneca reflects on the dynamics of vice in its more florid and imaginative forms (the examples analyzed here are letters 90 and 114), his terms frequently resonate quite specifically with ancient accounts of Neronian Rome (notably those of Tacitus and Suetonius) and other works of Neronian literature (particularly Petronius and Persius). As it turns out, highly refined vices even play a notable role in Seneca’s model of the development of philosophy.