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‘Who could put Seneca’s buskins on Homer?’ asks William Gager in the epilogue to his own Ulysses Redux, a neo-Latin tragicomedy which formed part of a trilogy of Shrovetide performance at Christ Church, Oxford in 1592. After the event, and as a result of the ‘anti-drama’ controversy with John Rainolds, Gager himself marketed this play – and academic drama more generally – as chiefly about moral edification: and the drama, with its strong central emphasis on the theme of fidelity, apparently offers us a typically ‘Renaissance’ Ulysses stripped of his scheming amorality. But, as Binns (1990: 130-1) points out, there is much more to this innovative play than its superficial moral message. My paper will explore whether analysis of the classical within the piece – that is to say, Gager’s fusion of the nostos of the Odyssey with the ‘Latin’ Ulixes of Virgil, Ovid and Seneca – contributes to a potentially more complex characterisation of Ulysses and in turn of the play itself, which in its playful self-awareness, preoccupation with disguise, strategies of audience interaction and focus on the sometimes disturbing conflation of humour and cruel action, clearly anticipates and echoes vernacular tragi-comedy more broadly. I will end by asking whether the ‘complex’ Ulysses of Shakespearian tragicomedy in Troilus and Cressida (1602) is necessarily as far different from Gager’s neo-Latin tragicomic Ulysses as we might at first glance think.