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The present series of investigations focused on an assessment of four humor styles—two positive styles (affiliative, self-enhancing), and two negative styles (aggressive, self-defeating)—individual differences in which are measured using the Humor Styles Questionnaire (HSQ). These styles of humor stand in contrast to the traditional concept of sense of humor, which has been shown to be vague and ultimately incapable of differentiating between positive and negative manifestations of humor. Across the investigations, the humor styles were assessed in relation to adaptive and maladaptive constructs to clarify the extent to which these functions of humor relate to indicators of adjustment and psychological well-being. Specifically, the variables were tested in conjunction with the intrapersonally adaptive construct of mental toughness, reflecting individual differences in resiliency and measured using the Mental Toughness 48 Inventory. They were also examined in relation to the Dark Triads traits (Machiavellianism, narcissism, psychopathy), representing interpersonally malevolent social strategies and assessed using three measures: the MACH-IV, the Narcissistic Personality Inventory, and the Self-Report Psychopathy Scale. The humor styles were also tested in relation to two models of personality: the six-factor HEXACO model measured using the HEXACO 60, and a tripartite trait-temperament model assessed via the Schedule for Nonadaptive and Adaptive Personality Self-Report Form. The goal of these latter investigations was to situate the humor styles within personality models that provide an alternative framework to contemporary five-factor structures, and to further assess the construct validity of the HSQ. Results revealed that the two positive humor styles are largely adaptive, reflecting tendencies toward greater mental toughness, convivial social strategies, proactivity, and positive affect. In contrast, the negative humor styles are predominantly maladaptive, correlating with poor mental toughness, avid interpersonal exploitation, diminished reciprocal altruism, and a propensity toward negativity affectivity and poor impulse control. Further, all four humor styles exhibited interpretable associations with the two alternative models, thereby demonstrating the construct validity of the HSQ. At the same time, the HEXACO model was deemed to be more effective than five-factor models in reliably capturing the nuances of adaptive and maladaptive humor styles in an etiologically informative manner.