This document assesses the introduction of pants roles in opera and includes a historical overview to understand the background of these roles. This dramatic conceit concentrates on the development of the operatic art form from the seventeenth to twentieth centuries. In Italy during the seventeenth century, the castrato voice, which had been a crucial aspect of church music, was now developing a position in opera. Within this document, the castrati’s transition from sacred music to the opera, where lies the bulk of their success, will be studied. As opera expands rapidly throughout the music scene, the demand of singers, specifically castratis, grew. The document will also deal with the introduction of castrati operatic roles. Gluck’s “Orfeo ed Euridice" is analyzed. Gluck’s opera exhausted several editions and demonstrates how the role Orfeo, as well as other castrati roles, evolved once castrato slowly went extinct. The terms referring to cross-dressing roles, and their specific repertoire, as well as the process in which women came to assume these roles will also be discussed. The shift from male to female in operatic repertoire is examined, as well as the traditional pants role for women in opera. The document will also discuss the pants role Cherubino as an example. This is the embodiment of a young boy in love, experiencing the admiration of a woman for the first time, as well as the vulnerability of his feelings for a woman. Cherubino’s arias are analyzed as well as a description and explanation of his possible intentions while singing his arias will communicate the subtext of the character. This document also discusses similar characters in Italian and French repertoire. The German repertoire for pants roles is separately presented and is based on the role of Octavian in Strauss’ Der Rosenkavalier. It is interesting that although the roles of Octavian and Cherubino were developed centuries apart, it is possible to compare similarities between the characters, from their creation, librettists’ perception and the composers’ execution in their compositions. This analysis was intended to exhibit the evolution of the pants role in opera and how writing current pieces for women in pants is an entirely different challenge as it was in previous centuries. In an attempt to expose different viewpoints on the subject, these questions will be addressed. The characters addressed so far are the pants; when a woman represents a male character. Meanwhile, there is a discussion about how a pants roles should be classified, although the pants role is the representation of a man played by a woman, she is not attempting to convince the audience that she is a man. The alteration of sex of a character when it is visible to the audience, and the conversation of categorizing a pants role; for example, the role of Leonore in Beethoven’s Fidelio, is debatable.