The purpose of this study is to present difficulties that arise from cultural differences in English translations of Nasreddin Hodja jokes. Nasreddin Hodja jokes are folkloric texts intervowen with subtexts, and they render it pass down Anatolian culture to next generations. Therefore, translation of those texts should be seen as an act of cultural transfer and the symbols and cultural elements in those texts should be translated carefully by considering their cultural and background information. In this study, translation evaluation of Nasreddin Hodja jokes was based on the concepts of semiospher, symbol, assymetry and cultural memory by Yuri Lotman who considered the act of translation as culture. First, the concept of humour was analyzed with an association built between Lotman’s concepts and Nasreddin Hodja jokes. Then, the difficulties in the translation of cultural elements in Nasreddin Hodja jokes were discussed with examples identified in accordance with Lotman’s concepts. The analysis of translation showed that while some translators avoid translating the cultural elements unique to the source text culture and wipe out the sign in the target text, some translators directly transfer the cultural element from the source culture without explication or elaboration of those items, and still some others use the target culture equivalance of those cultural elements. The difficulties in translation of cultural elements as found in the examples in this study, were ascribed to lack of cultural background information. In this sense, semiotical analysis and interpretations of source text prior to the act of translation could help the translators in transformation of cultural elements and contribute to the intercultural communication function of translation.