Objectives: Hearing difficulty is prevalent in older adulthood and projected to increase via global aging, particularly among men. Currently, there is limited research on how this gender disparity might vary by country. Methods: Using 2018 data ( n = 29,480) from the Health and Retirement Study (HRS) international family of studies, we investigate gender disparities in hearing difficulty among respondents ages 55–89 from the United States ( n = 12,566), Mexico ( n = 10,762), and Korea ( n = 6152) with country-specific ordinal logistic regression models that progressively adjust for demographic, social, and health indicators. Results: In the United States, men’s hearing difficulty disadvantage was consistently observed. In Mexico, men’s hearing difficulty disadvantage was explained by the interactive effect of gender and age group but resurfaced after adjusting for comorbidities. In Korea, there was consistently no gender difference in hearing difficulty. Discussion: Our results highlight the heterogeneity in older men’s hearing difficulty disadvantage among a diverse group of aging countries.