This research paper is on youth employment and entrepreneurship. It investigates a total of 3,591 youths in two different geographical areas of Ethiopia, i.e., central and eastern. In doing so, it has taken three specific villages: Melka Jebdu and Gedenser (Eastern Ethiopia) and Wereda 10 (Addis Ketema, central Ethiopia).The core objective of the study is to assess the issues related to youth unemployment and entrepreneurship in Addis Ababa and Dire Dawa. Some of the specific objectives set are: to determine the unemployment rate for male and female youth in the selected Kebele/Sub city; to determine the magnitude /proportion of the unemployed across population subgroups (by age group, sex and urbanity); and to identify major bottlenecks for the female and male youths in starting up a business in the selected two areas. The census finding shows that youth unemployment rate is at an aggregate of 11.39 percent for the project sites. Specifically, the prevailing youth unemployment rate in the project site in Addis Ababa is 10.06 percent. In contrast, the two sites in Dire Dawa sites, namely, Melka Jebdu and Gedenser, have youth unemployment rates of 12.87 percent and 20.34 percent, respectively. In addition, the study finds that the major cause for the youth not to engage in self- employed job is capital. The research has also tried to determine how unemployment is reflected in terms of gender. In this regard, the results based on the data indicate that the hypothesis saying that unemployment prevails more among females than males is totally false. Generally, this paper has investigated issues like: factors affecting the youth’s being self-employed in the overall project sites, the involvement of the youth in extra jobs, and the degree of influence of various factors on the youth’s being self-employed.