This study contributes to cross-cultural humor research in an understudied genre, namely entertaining semi-structured man-on-the-street interviews. Two entertainment shows, Egyptian الشارع مذيع /muði:ʕəʃʃae:riʕ/ 'street broadcaster' and American Pedestrian Question (PQ) segment in Jimmy Kimmel Live, pose humorous questions to random pedestrians. Within a comprehensive framework integrating three theories of humor (Superiority, Incongruity and Relief), the humor dimensions/styles (Martin et al., 2003), and Culpeper's (1996, 2005, 2011a, 2011b Model of Impoliteness, this study contrastively investigates the humor styles and themes intended through PQs in 80 YouTube video clips. Two styles have been identified in both shows: aggressive otherdeprecating and affiliative relief-based. The former, mapped to impoliteness strategies, may feed audience's feelings of superiority at the pedestrians' expense. The latter may offer the audience 'voyeuristic pleasure' while deriving relief from pedestrians' confessions, fantasies, and the daring of authority. In confessions and fantasies, PQ themes are conservative on the Egyptian show but often unorthodox on the American show. The study further explores the effect of culture and humor style on YouTube viewers' appreciation measured by percentage of likes (%Likes). The effect of culture has only been statistically significant regarding relief-based humor, where Egyptian clips have achieved more %Likes than have the American clips.