In Japan, complimenting one’s superiors is usually considered inappropriate. This is because the act of complimenting intrinsically has the connotation of evaluating the complimented party, and juniors are considered not possessing sufficient knowledge, experience or ability to evaluate their superiors. On the other hand, complimenting one’s superiors does not seem to be uncommon in English-speaking countries. The difference in perception on complimenting superiors could become source of confusion especially when Japanese college students start to work in English-speaking business environments. In order to deepen the understanding of how complimenting superiors work when communicating in English, the paper investigated the intentions of compliments and how they are expressed by analyzing and comparing American and Japanese movies and dramas depicting business environments where superior-subordinate relationships were clearly manifested. A new framework was created to categorize and analyze the compliments by combining 2 existing frameworks. Leech’s ‘The Tact Maxim’ was used for consideration. The results showed that when people complimented their superiors in English-speaking environments, the compliments were (1) meant to express high evaluations in all sincerity, (2) expressed to the superiors directly, (3) decisively expressed by evaluating the superiors or their deeds, and (4) expressed by concretely presenting facts.