We examined the influence of personality traits on mean levels and age trends in 4 single-item measures of self-rated health: general rating, comparison to age peers, comparison to past health, and expectations for future health. Community-dwelling participants (N = 1,683) completed 7,474 self-rated health assessments over a period of up to 19 years. In hierarchical linear modeling analyses, age-associated declines differed across the 4 health items. Across age groups, high Neuroticism and low Conscientiousness, low Extraversion, and low Openness were associated with worse health ratings, with notable differences across the 4 health items. Furthermore, high Neuroticism predicted steeper declines in health ratings involving temporal comparisons. We consider theoretical implications regarding the mechanisms behind associations among personality traits and self-rated health.