Contemporary images of desirable work (for example at gaming companies or at one of the tech giants) foregrounds creativity and incorporates and idealises elements of play. Simultaneously, becoming one of the best in some particular leisure activity can require many long hours of hard, demanding work. Between on the one hand work and on the other hand leisure and play, we enter the domain of games and sports. Most classical sports originally developed from physical practices of moving the human body and these practices were, through standardization, organization and rationalization, turned into sports. Many sport researchers, (sport) historians and (sport) sociologists have pointed out that sports have gone through a process of “sportification”. Cross-country skiing is an example of an activity that has gone through a historical process of sportification, over time becoming progressively more managed and regulated. Computer games are today following a similar trajectory and have gone from being a leisure activity to becoming a competitive activity, “e-sports”, with professional players, international competitions, and live streams that are watched by tens of millions of viewers. In this paper we look at similarities between the sportification of cross-country skiing and e-sports. While there are many similarities, one important difference is that where classical sports (e.g. cross-country skiing) often originated in work-related practices (in this case forestry), the formation of new and emerging sports (for example e-sports) instead often originates in playful leisure activities. We will in this text show how sports and sportification processes can function as a lens with which to better understand the intersection of work and play, and well as their overlapping and hybrid albeit non-mutually exclusive combinations; laborious play and playful work.