Tobacco smoking has been found to be significantly associated with a decreased chance of reaching longevity in men, but not in women. Furthermore, it is still unclear how the association of smoking status with longevity varies under the influence of underlying smoking characteristics. Therefore, we aimed to quantify the association between several smoking characteristics and the chance of reaching the age of 90 years in men and women separately. We carried out a prospective cohort study among the oldest birth cohorts (1916-1917) of the Netherlands Cohort Study, who completed a baseline questionnaire in 1986 (at ages 68-70), and had complete vital status information until 90 years-of-age (2006-2007, n = 7807). Multivariable-adjusted analyses were based on 6642 men and women, of which 16.0% and 34.3% reached longevity, respectively. The relationship of smoking status with longevity was stronger in men than in women (current vs never smokers; risk ratio 0.44, 95% CI 0.34-0.56 in men, and risk ratio 0.67, 95% CI 0.57-0.79 in women). Furthermore, significantly inverse associations were found between longevity and increasing cigarette smoking quantity, duration, and tar and nicotine exposure, which partially explain the observed difference between both sexes. Quitting smoking significantly increased the chance of reaching longevity compared with current smokers. The effect of smoking status on reaching longevity seemed stronger in men compared with women, which can be partially explained by differences in smoking habits. Never smokers had the highest chance of reaching 90 years-of-age in both sexes. Geriatr Gerontol Int 2018; 18: 1249-1258.