Three dimensions of overall health are defined by the World Health Organization-physical, mental, and social. Psychological well-being has been a popular research topic recently and has been shown to relate to mental health. The analysis of distinct population groups offers unique opportunities for the investigation of the interplay of the psychological, social, and physical elements of health. This study characterizes the psychological wellbeing of a unique, high stress occupational group, United States Air Force fliers (pilots and navigators). Data were obtained from a cross-sectional “Health Survey” of male fliers and nonfliers with 2485 respondents. Mental health was ascertained with an index of psychological well-being (PWB). Additionally, other data relevant to health status were collected. Results of the Alameda County, California, survey of PWB were also used for comparison. Data were analyzed using analysis of covariance and multiple linear regression. Fliers were found to have significantly better PWB than nonfliers; this finding is in accord with clinical folklore regarding differences between fliers and nonfliers. Both Air Force groups had better PWB than that reported for Alameda County. There were no significant differences between pilots and navigators and no differences between pilots of different types of aircraft, results which contradict previous anecdotal reports. Young (age 21 to 28) active pilots were found to be a distinct group with significantly better PWB than any other group. Several variables made small but statistically significant contributions to explaining the variance in PWB. The best correlates of PWB were better self-reported overall health, lack of perceived time pressure, more competitive behavior, and a positive attitude toward physical fitness. The results are discussed in terms of the flier selection process, the intrinsic differences in those who select flying as a vocation, and the interaction of the flier’s developmental stage and his environment.