Purpose: Few studies have examined the behavioral and clinical indicators of sleep difficulty among older African Americans diagnosed with arthritis. This study aimed to examine the association of sleep, pain, and comorbid indicators among this population. Method: Using a cross-sectional design, 193 older African Americans (70.4 ± 9.11 years of age) completed a series of questions assessing health, pain, and sleep. Results: Findings showed that young old participants (β = –.28, p < .001) reported more difficulty sleeping and being awakened due to pain (β = –.17, p < .05) than the old old adults. Conclusion: There is significant within-group variability, with young old adults being most affected by sleep difficulties. Implications for Practice: While the relationship between pain and sleep may be intuitive for majority populations, the dynamics of this association may be useful in promoting sleep awareness and providing resources for caregivers and health care professionals to better meet the needs of this population.