This article reports a two-part study into the prosocial impacts of third sector cultural activities with children and adolescents in impoverished and violence-stricken urban neighbourhoods in Cali, Colombia. First, a year-long field study set out to compare a pre-existing music-training programme with a dance-training programme and a football-training programme with 9–14 year olds, to determine the extent to which each affords the development of empathic attitudes and prosocial behaviours. The music and dance programmes produced few significant changes in participants’ empathy or prosociality, and there were few significant differences between the empathy and prosociality of the participants in the two groups. Participant dropout prevented comparison with the football-training programme. Second, an interview study was used to understand the place of prosociality in the aims and work of policymakers, funders and third-sector practitioners running cultural activities for social impacts in the Cali region. The study revealed that the organisations aimed to achieve individual and social transformation by creating the conditions for transformation, evidenced as positive outcomes. Neither the measures used by the organisations themselves nor the psychosocial constructs of prosociality and empathy used by the researchers adequately evidenced some of the intended outcomes, such as enabling individuals to build a life project, practising and sustaining social inclusion and transforming communities, nor a path from individual to social transformation. Differences between the structure of cultural activities and their associated values meant that different activities were believed to lend themselves to social transformation more or less well. This highlights the need for critically reflective, co-constructed research using a fuller range of constructs that can capture the outcomes of these programmes for both individuals and groups.