This article discusses the role of engraved gems in manifestation of philosophical views of the Romans concerning death, vanishing and afterlife as well as their social status. First, it concentrates on a group of rare intaglios, generally dated between 1st century bc to 1st century ad featuring various subjects combining on the one hand skeletons, skulls, backbones, butterflies, torches etc.—elements associated with death and vanishing and on the other hand components related to Bacchus, banquets and joys of life like thyrsus, wine amphorae, astragals, paterae etc. The traditional interpretations linked them to the Epicurean attitude encouraging to enjoy life because one must die. However, it is noteworthy that the ‘macabre gems’ include elements like laurel wreath or festoons employed in the way suggesting a strong belief in afterlife and ultimate victory over death. This is much in accordance with the Stoic philosophy. Furthermore, the paper expands and analyses a variety of subjects like a philosopher contemplating a skull or skeleton, Eros-Thanatos, Eros tormenting a butterfly (psyche) with a torch, a butterfly as a symbol of soul and many others that can be ultimately linked to the same realm and concept of death and vanishing. Finally, examples are proposed that probably illustrate personification of Death itself on gems. All in all, the ‘macabre gems’ as well as their more distant peers prove that small and highly personal objects like intaglios could communicate various things at the same time and interpretation of a single object should be done with a reference to the group of its fellows. The article argues that the appearance of the ‘macabre gems’ was connected to the di√cult and tragic times of the Roman Civil Wars.