Men's poor health behaviors are an increasingly prevalent issue with long-term consequences. This study broadly samples Canadian men to obtain information regarding health behaviors as a predictor of downstream medical comorbidities. A survey of Canadian men included questions regarding demographics, comorbidities, and health behaviors (smoking and alcohol consumption, sleep and exercise behaviors, and dietary habits). Health behaviors were classified as either healthy or unhealthy based upon previous studies and questionnaire thresholds. Multivariate regression was performed to determine predictors for medical comorbidities. The 2,000 participants were aged 19-94 (median 48, interquartile range 34-60). Approximately half (47.4%) were regular smokers, 38.7% overused alcohol, 53.9% reported unhealthy sleep, 48.9% had low levels of exercise, and 61.8% had unhealthy diets. On multivariate analysis, regular smoking predicted heart disease (OR 2.08, p < .01), elevated cholesterol (OR 1.35, p = .02), type 2 diabetes (OR 1.57, p = .02), osteoarthritis (OR 1.43, p = .04), and depression (OR 1.62, p < .01). Alcohol overuse predicted hypertension (OR 1.40, p < .01) and protected against type 2 diabetes (OR 0.61, p < .01). Unhealthy sleep predicted hypertension (OR 1.46, p < .01), erectile dysfunction (OR 1.50, p = .04), and depression (OR 1.87, p < .01). Low levels of exercise predicted hypertension (OR 1.30, p = .03) and elevated cholesterol (OR 1.27, p = .05). Finally, unhealthy diet predicted depression (OR 1.65, p < .01). This study confirms the association of poor health behaviors and comorbidities common to middle-aged and older men. The results emphasize the potential scope of targeted gender-sensitized public awareness campaigns and interventions to reduce common male disease, morbidity, and mortality.