This introduction to emoticons, kaomoji, and emoji gives a short survey of the state of research surrounding digital pictograms and ideograms. It proposes to connect reflections on the communicative, semiotic, sociopolitical, and aesthetic transformations of digital communication. While emoji have so far either been treated as a mainly ‘Japanese’ phenomenon or as a ‘universal’ form of expression, neither of these is particularly helpful to trace transnational flows, border-crossings, and international crossovers, which are among the main interests of the present volume. The editors place these approaches and discourses within the perspectives of media theory and (inter)cultural studies. This allows for a multidimensional concept of media and mediality that affords the distinction among a communicative-semiotic, a material-technological, and a conventional-institutional dimension of digital pictograms and ideograms. The potential of this model is then exemplified by means of a discussion of a recent political interview conducted entirely via emoji characters. The respective forms of emoji ‘mediation’ could be understood as negotiations between the technological, the semiotic, and the social, between individual, as well as corporate, actors. Emoticons, kaomoji, and emoji constantly shape and facilitate specific forms of structured agency that often remain invisible. After providing a discussion of these transformations of communication in the digital age, the introduction concludes with an overview of the (following) contributions within this volume.