This research paper is on youth employment and entrepreneurship. It has investigated a total of 3591 youths in two different geographical areas of Ethiopia. Entirely, it has taken three specific villages: Melka Jebdu, Gedenser (eastern Ethiopia), and Wereda 10 (Addis Ketema, central Ethiopia). The core objective of the study was to assess issues related to youth unemployment and entrepreneurship in major cities of Addis Ababa and Dire Dawa. Some of the specific objectives set were to determine unemployment rate for male and female youth in the selected Kebele/ Sub city, determine the magnitude/proportion of the unemployed across population subgroups (by specific age bracket, by sex, and by urbanity), and similarly identify major bottlenecks for the female youth and male youth to start up own business in the selected two areas. As a springboard for conclusion, the following hypotheses were set: the level of female youth unemployment exceeds male youth unemployment, financial constraint is the most critical bottleneck to start up a new business in the selected sites, the youth is suffering from unfair competition and corruptive employment actions, and youth in the area lack training related to starting their own venture. As a tool of descriptive data analysis and presentation, in this study, frequency tables have been utilized in depth. Moreover, binary logistic regression predicting and analysis tool has been used to check the prospect of youth self-employment in the study sites. The census finding shows that youth unemployment rate is at 11.39% aggregately for the two project sites. Specifically, the study site at Addis Ababa prevails youth unemployment rate of 10.06%. Contrastly, the two sites in Dire Dawa sites Melka Jebdu and Gedenser have youth unemployment rate of 12.87 and 20.34% consecutively. In addition, it has found that the major cause of youth not to engage in self-employed job is related to capital financing. The research has also tried to determine how unemployment is reflected gender wise. Accordingly, the aggregate data shows hypothesizing that unemployment are highly prevail on female than on male in the localities is totally false. Generally, this paper has investigated issues like factors affecting youth prospect to be self-employed in overall study sites, the involvement of youth in multiple jobs (employments); it also indicates the degree of influence of various factors on youth to be self-employed. Finally, this study has provided vital conclusions and policy recommendations to handle youth’s employment/unemployment and entrepreneurship issue specific to the study areas.