Background/objectives: To assess the effect of humor on IGT decision-making as a function of gender, and to explore the neural correlates underlying this effect. Method: We randomly assigned participants (N = 60; 30 men and 30 women) to either an experimental Humor Group (Hg) or a control non-Humor Group (NHg) and asked them to perform a long-version (500 trials) of the Iowa Gambling Task (IGT). Participants’ EEG response was recorded while solving the IGT. Results: Men in the Hg demonstrated impaired monitoring and learning of the task compared to men in the NHg. Later, women in the Hg, exhibited more integrated attention to rewards and punishments along with a decrease in random choices when compared with women in the NHg. Behavioral and EEG results support that humor is beneficial for women’s cognitive control of IGT performance but impairs it in men.