There were several research goals, the main of which include investigating any potential differences between the generations with regards to the level of entitlement, analysing potential determinants of entitlement among socio-demographic variables and the potential link between entitlement and the general ideological orientations on the Croatian population. Two instruments were applied on the research sample that enumerates a total of 217 participants of both genders (127 women and 90 men): the one constructed anew for the purposes of this research to assess the level of entitlement and the general ideological orientations questionnaire (Proroković 2016). It is also important to add the routinely applied questionnaire for determining participants’ basic socio-demographic characteristics. Three generations were encompassed by the study: Generation Y (N=108), Generation X (N=69) and Baby Boomers (N=40), according to the categorization and the chronological framing by Strauss and Howe (1991). The results of the research have indicated significant differences in the level of entitlement across different generations. As theorized, the greatest level of entitlement was found in the Generation Y, followed by Generation X and finally Baby Boomers. Furthermore, greater level of entitlement correlated positively with the left-wing orientation in all generational subgroups. When it comes to potential determinants of entitlement among the examined socio-demographic data, religiosity and gender were proven significant across generations, also with the company-wise type of employment as a determinant in older generations. Nonreligious individuals and men showed significantly lower levels of entitlement, while those working in public sector showed the greatest entitlement in relation to those unemployed or working in private sector.