This paper examines the labor market status of older males in the era of industrialization, focusing on the question of how the extent of pressure toward retirement varied across different occupations, and how it changed over time. A comparison of hazard of retirement across occupations shows that men who had better occupations in terms of economic status and work conditions were less likely to retire than were those with poorer jobs. This result tends to reject the recent view that retirement was more voluntary than forced as early as a century ago. The difficulty faced by older workers in the labor market, as measured by the relative incidence of long-term unemployment, was relatively severe among craftsmen, operatives, and salesmen. In constrast, aged farmers, professionals, managers, and proprietors appear to have fared well in the labor market. The pattern of shifts in the occupational structure that occurred between 1880 and 1940 suggests that industrialization had brought a growth of the sectors in which the pressure toward departure from employment at old ages was relatively strong.