Objectives This work aims to test the hypothesis that the funniest comedians are most at risk of a premature death and reduced longevity compared to their relatively less funny counterparts. Methods A retrospective longitudinal cohort study with a nested case-control analysis of longevity of 53 male British comedians born between 1900 and 1954 was conducted. All comedians were given a subjective score from 1 (relatively funny) to 10 (hilariously funny) by the study investigators. The survival profile of all comedians was then examined adjusting for decade of birth, whether they worked in a comedy team and their comedy score. A nested case-control analysis examined the longevity of those comedians working in teams according to their pre-specified status within the team (straight/less funny versus funny team member). Results On an adjusted basis, there was no correlation between the decade of birth (HR 0.94, 95% 0.65 to 1.38 per incremental decade; p = 0.763) and comedy team status (HR 1.13, 95% 0.51 to 2.48 versus independent comedian; p = 0.761) with longevity. However, an increasingly funny comedy score was associated with increased mortality (HR 1.24, 95% CI 1.06 to 1.44 per unit funny score; p = 0.006). Of the 23 comedians adjudged to be very funny (score 8-10), 18 (78%) had died versus 12 (40%) of the rest; mean age at death 63.3 ± 12.2 versus 72.3 ± 14.7 (p = 0.079). Within comedy teams, those identified as the funnier member(s) of the partnership were, on an adjusted basis, more than three times more likely to die prematurely when compared to their more serious comedy partners (HR 3.52, 95% CI 1.22, 10.1; p = 0.020). Conclusions These data suggest that elite comedians are at increased risk of premature death compared to their less funny counterparts. Mental health issues and personality characteristics that help shape their comedic talent and success may well explain their reduced longevity and raises serious issues for identifying and mitigating their risk of a premature death.