In the last 150 years, the ambiguous and enigmatic 81 chapters of the Tao Te Ching have been translated, interpreted and adapted into the English language more than 100 times. The Tao and its subtle philosophy is currently being actively assimilated into mainstream western culture as evidenced by the popularity and volume of Taoist works. The purpose of this study was to analyse this phenomenon. First, a database of English translations of the Tao Te Ching was established. This database documents the vast number of Tao Te Ching translations in print from 1868 to the present. Second, specific chapters of selected English translations of the Tao Te Ching were compared using holistic and content analysis. The holistic methods focused on the overall semantic connotation of the selected chapters. The specific (linguistic) analysis methods entailed the use of a computerised content analysis program (hyperRESEARCH for Macintosh). Through these inquiries, a specific understanding of the cross-cultural relationship between East and West was investigated.