The current study sought to examine the demographic, psychosocial, and cultural predictors of psychological entitlement (PE) and academic entitlement (AE) and their impacts on psychological well-being in a sample of Asian and Caucasian young adults in Canada. This study found that on average, less than 80% of the participants endorsed items characteristic of entitlement. Based on multiple regression analyses, higher PE was predicted by unemployment, older age, more recent generation status, and a weaker tendency for social comparison. Higher AE, on the other hand, was predicted by younger age, more recent generation status, lower self-esteem, and lower self-efficacy. AE was found to be negatively associated with a number of psychological well-being indicators, while PE was not. The results suggest that entitlement in the form of AE may be more problematic as compared to PE. With respect to ethnic differences, PE and AE were higher among Asian Canadians than Caucasian Canadians. Implications for future research and practice are discussed.