Although the deleterious physical effects of smoking have long been documented, smokers often claim that there are compensatory psychological benefits which accompany the use of cigarettes for sedation or pleasure. This paper summarizes a series of studies undertaken to test the hypothesis that for some individuals, certain kinds of cigarette smoking may contribute to psychological well-being. Measures of life stress, age, and the 3 personality dimensions of neuroticism, extraversion, and openness to experience were collected on a sample of 1101 adult male volunteers. Smoking status, smoking motives, and psychological well-being were also measured. Results showed that a) both personality and smoking motives show a replicable factor structure and are stable over many years; b) age, life stress, and demographic variables show little relation to psychological well-being, whereas the personality variables of neuroticism and extraversion show stronger relations; c) smoking is associated with neuroticism, but not with extraversion; and d) neither smoking itself nor smoking for any particular motivation shows any effect on psychological well-being. It is concluded that the psychological “benefits” reported for smoking are illusory, and that alternative coping strategies should be pursued.