One of the evolutionary functions of humor for men is to connote their interest to women. However, women’s prioritization of humor from prospective mates could foster especially judicious criteria for humor quality, which may have led selection to favor particularly funny men. The current research presents four studies comparing the desirability of men whose humor displays vary in quality (i.e., funny versus unfunny). Women prefer men capable of successful humor despite viewing both humor displays as similarly friendly (Study 1). This preference appears to be rooted in perceptions of investment potential (Study 2) and especially apparent for long-term mating (Study 3). Physical attractiveness additionally heightens a preference for funny men (Study 4). The mere connotation of interest through humor appears insufficient without the display actually being funny. We contextualize results from complementary perspectives of humor being sexually selected and connoting interest.