A simple model of human motivation suggests that people “avoid pain + pursue pleasure.” For many, other people can be the sources of both unwanted pain and desirable pleasure. People have gone online to entertain each other for decades. In this attention economy, those who can drive traffic and capture “likes” and other forms of favoriting become stars for a fleeting moment or two. Even as different micro-celebrities rise and fall, some of the energy online is towards distracting and soothing each other through various forms of fun and challenge and feats and humor. There is the vicarity of the performance, with fans able to “co-experience” the efforts of peers showing various skills and scenes. Looking at the social shares on the Social Web through an entertainment lens shows a space full of dancing, singing, joking, eating, feats of daring, modeling, storytelling, secret sharing, performance art, drama, and other social performances. People go online to meet their own needs and to meet the needs of others. Some portion of peer-shared online contents is designed to meet the hedonic- or pleasure-seeking needs of others through various forms of social sharing (as entertainment). There are particular forms of entertainment targeted to particular audiences. It is as if people are speaking to each other in particular love languages, with particularities and resonances, unique meaningfulness to particular segments of the population. What draws human attention and holds it may differ for different groups. People experience their own particular forms of delight, from different pleasures for the minds and senses. Different “fairytales” and illusions and preferred narratives appeal to different groups, based on learned enjoyments and positionality. In the Social Web space, particular performances lead to mutuality and sharing and commenting and mass attention. This dynamic holds for niche audiences, too. This book explores peer-shared entertainment on the Social Web in its various forms, in a competitive attention economy.