This article is about success, its positive aspects and, unfortunately, its negative aspects. Since most individuals are motivated to seek success from early on, what happens when an individual becomes quite successful and then believes he/she is more deserving of it? Such individuals often develop an overblown self-belief system, suggesting a high level of entitlement and an exaggerated sense of hubris. The growth of this entitlement often is encouraged from an array of individuals, including those closest to him/her, as well as agents--even fans. A look at the dark side of success, as well as some consequences, is presented. Also offered is a formula suggesting the path considerable success can take and its potential negative aftermath. The article underscores what happens when success, especially great success, goes awry.