Objective: To investigate the association of musculoskeletal pain with objectively determined obstructive sleep apnea (OSA) and subjective sleep measures in a population-based sample. Methods: Participants were community-dwelling men (n = 360) age ≥35 years from the Men Androgen Inflammation Lifestyle Environment and Stress (MAILES) study. Shoulder, back, hip, knee, hand, and foot pain were assessed by computer-assisted telephone interview or self-completed questionnaire. OSA was determined with full in-home unattended polysomnography (Embletta X100) scored by 2007 American Academy of Sleep Medicine alternative criteria. The Epworth Sleepiness Scale assessed daytime sleepiness and the Pittsburgh Sleep Quality Index assessed sleep quality. Results: OSA was not associated with the presence of any joint pain (adjusted odds ratio [OR] 1.03 [95% confidence interval (95% CI) 0.61–1.76]). There was no association between OSA and pain in any specific joint (shoulder, back, hip, knee, hand, or foot), nor was the number of joints in pain associated with OSA. There was, similarly, no association between pain variables and excessive daytime sleepiness, except for hand pain (OR 3.10 [95% CI 1.50–6.39]). However, pain was associated with poor sleep quality: any pain (OR 2.19 [95% CI 1.25–3.82]), shoulder pain (OR 2.16 [95% CI 1.25–3.75]), back pain (OR 2.24 [95% CI 1.41–3.55]), and foot pain (OR 2.47 [95% CI 1.43–4.26]). The number of painful joints was also associated with poor sleep quality (5–6 joints versus no joints OR 7.34 [95% CI 2.30–23.42]). Conclusion: No association between OSA and pain or between daytime sleepiness and pain was found. Consistent with previous reports, poor sleep quality was associated with musculoskeletal pain in this population sample. The etiologic differences between OSA-related sleep disruption and poor subjective sleep quality require further investigation.