This chapter focuses on the impact of urbanization in regional labor markets of various European states, comparing the regional context in 1972 and 2022. Central Europe showed high and homogeneous levels of urbanization across the territory, while Mediterranean regions exhibited greater disaggregation and a tendency toward polarization. The Italian case—with the distinction of the “three Italies”—is particularly interesting. The North, highly developed and urbanized; the South, struggling for long-term development; and the Center, situated between the two. In this view, urbanization has had a significant impact on the economic structure and labor market, with metropolitan areas like Milan and Turin benefiting from economies of scale and a higher concentration of advanced services. In contrast, the South has suffered from lower industrial density and slower economic growth, despite some recent improvements. Another case of interest is Spain, where localization and urbanization economies influence the location of new manufacturing enterprises. Urbanization economies prevailed in knowledge-intensive sectors, suggesting that these businesses locate in large cities to benefit from knowledge spillovers. In Germany, specialization and city size influenced employment growth, with larger cities offering more job opportunities and resources, and with benefits diminishing beyond a certain size due to agglomeration diseconomies. We concluded emphasizing how understanding these differences is crucial for conducting balanced development policies between urban and rural areas, promoting innovation, education, and vocational training in peripheral areas to reduce regional disparities and improve labor market equity.