Digital writing is strikingly playful. This playfulness flourishes particularly in synchronous chat modes on the Internet. This paper is a study of writing, play and performance on IRC (Internet Relay Chat). We analyze a “virtual party” on IRC, whose highlight was a typed simulation of smoking marihuana. Three interrelated, yet analytically distinct types of play are discussed: 1) play with identity; 2) play with frames of interaction; and 3) play with typographic symbols. We adopt a qualitative, textual, and micro-sociolinguistic approach, drawing on work in discourse analysis, the study of orality and literacy, and the anthropology of play and performance. In all play there is reduced accountability for action. In the material world, masks and costumes at carnival time liberate participants; here, the ephemeral, non-material medium, the typed text, and the use of nicknames provide the mask. Although the improvisation analyzed here is typed and occurs between geographically dispersed strangers, it has fascinating affinities with “live” interactional forms such as jazz, charades, and carnivals.