Up until now the domain of literary critics, counterfactual fiction and uchronic narratives are here analysed by ancient historians and classicists, shedding important new light on how cultures of the ancient world are perceived now and to what extent our experience and perception of the past is used to explore alternate presents and futures. Alternate history entices the imagination of the public by suggesting hypothetical scenarios that never occurred, characterised by one scholar as a latent tension between artificiality and authenticity. This interest has resulted in a growing number of publications that gauge the impact of what-if narratives, and this one is the first to give ancient historians the stage. Focusing in turn on history, politics, the arts and under-represented voices, the essays in this collection cover a wide variety of modern and contemporary fiction from Pauline Hopkins and L. Sprague De Camp to T. S. Chaudhry and Catherynne M. Valente. Chapters look into the question of chance vs determinism in the unfolding of historical events; the role individuals play in shaping a society or occasion; and the way art and literature symbolise important messages in counterfactual histories. They also show how uchronic narratives can take advantage of modern literary techniques to reveal new and relevant aspects of the past, including ensuring that marginalised and suppressed individuals in the ancient world, from women to slaves to minorities, can now take centre stage.