The rise of cringe comedy is one of the most notable developments in twenty-first-century comedy, distinct from traditional embarrassment humor by being aimed at evoking not just humor but also vicarious embarrassment (i.e., “cringe”) in audiences. While made globally, the most successful examples of the genre stem from the UK and the US, each marked by their originating culture. This chapter compares three British cringe comedies—I’m Alan Partridge (1997–2002), The Office (2001–2003), and Peep Show (2003–2015)—with two American equivalents—Curb Your Enthusiasm (2000–2024) and the US adaptation of The Office (2005–2013). Despite using similar techniques to decrease psychological distance and evoke cringe at their protagonists’ embarrassing social violations, British and American cringe comedies ultimately invite contrasting judgments of their central characters. Reflecting British vs American values of conformity vs authenticity, respect for others vs independence, and humility vs self-belief, British cringe comedies portray their protagonists negatively, as cautionary examples of how not to behave, while American protagonists are unlikely heroes, with their tendency to violate norms ultimately coming through as strengths rather than defects. This is reflected in how often episodes end happily for them, with happy endings more than twice as frequent in the American cringe comedies.