Really creative posts on the social media accounts of brands or political parties can produce gratifyingly viral results that can boost brand engagement, loyalty, profits and votes. This makes it a highly attractive new marketing tool. However, when brands or parties get creativity on social media wrong it can damage reputation. This chapter examines two aspects of this trade-off between the viral and the virtuous. Firstly, the authors explore the regulations around labelling brand posts as adverts and show that they are very unclear, tempting brands to bend the rules or allowing them to inadvertently break them. Secondly, the authors consider memes: a content marketing technique widely used in political and commercial brand posts. The authors analyse the three creative elements core to memes along with successful and unsuccessful examples. The authors end by suggesting that regulators clarify the codes and invite readers to weigh up the pros and cons of using creative content marketing in brand posts.