Using data from the 1990 U.S. Census and the 2006-2007 American Community Survey (ACS) and a synthetic cohort method, this article examines the labor market performance of young men during their initial transition to work and how it differs by educational attainment and race. The article looks at young men between the ages of 16 to 26 in 1990 who were no longer enrolled in school and men between the ages of 32-33 and 42-43 in the 2006-2007 period. Strong patterns in the results confirm conventional wisdom that economic and labor market outcomes are superior with increased levels of educational attainment. However, outcomes were more dramatic for those with college degrees than others (relative to those who dropped out of high school), confirming the disproportionate value of obtaining a college degree. Graduating from high school, going to community college, or receiving an associate's degree also improved outcomes. The data revealed that not acquiring a high school degree, especially for domestic-born racial minorities, generates very poor labor market outcomes during the initial transition to work. Racial inequality in labor market and economic outcomes widened as educational attainment levels increased. These results strongly suggest that efforts to boost academic achievement and educational attainment of racial/ethnic minority men, although they may improve labor market and economic performance, will probably not narrow racial inequalities in outcomes. Programs and policies should target factors that limit the potential gains in the labor market from educational attainment for these men. (Contains 11 tables and 10 footnotes.)