This chapter focuses on the importance of entertainment in brands/marketing media and channels for consumers. An engaging story relies on a good plot, well-developed characters, conflicts and resolution. Most consumers want entertaining material that is eye-catching, original and relatable. Consumers are still seeking the same characteristics that any excellent tale has, but without the sense that it is artificial or fabricated. Authenticity is paramount. Furthermore, as the Internet and digital technologies become more accessible, brands must try to generate content that can attract consumers’ attention and lead to longer-term engagement and connections. The chapter concludes with an exploration of how brands should embrace this shift in content consumption by adjusting their tactics to produce tales that resonate with their target audience.