Yemen has a reputation across the Middle East for the production of traditional poetry, music and dance, but is rarely associated with drama or the theater. Yet the country has had a long and vibrant theatrical history, and has produced gifted and prolific playwrights whose work provides vital and unique insight into the culture, the concerns, and the aspirations of her inhabitants. Throughout the 20th century and into the 21st, Yemeni acting troupes have practiced in all of Yemen’s major cities, performing a range of genres, from classical Greek tragedy to musicals to experimental drama. Yemeni playwrights have created comedies, satires, historical dramas featuring the Queen of Sheba and Saif Bin Dhi Yazen, and have adapted the works of Western authors like Shakespeare, Brecht, and Pirandello to their own historical and societal context. Contemporary dramatic performances attract hundreds of enthusiastic spectators; theater productions are commissioned for festivals, holidays, and even wedding celebrations. This paper will examine the roles played by women in contemporary Yemeni theater, as protagonists and heroines of particular plays, and also as actresses, directors, and critics. It will highlight the intense scrutiny to which Yemeni actresses are subject and investigate the occasionally, harsh criticism, when they step into the limelight. Research methodology will combine translation and textual analysis grounded in performance theory, with evaluation of the visual iconography of various performances viewed in Sana’a and Aden. The paper will reference the recent work of Yemeni theater critics such as Yahya Mohammed Saif, as well as personal interviews with actresses Nour Abdullah and Manal al-Mulaki, and playwright-directors Amr Jamal and Qasim Abbas al-Lami, among others. One objective of this paper is to show how women capitalize on the freedom of expression that playing a role on the liminal space of the stage can provide. It will therefore cite the obstacles that all practitioners of contemporary theater in Yemen must struggle against, especially the social strictures that set rigid limits on what opinions may be voiced in public, and on male-female interaction. Providing specific examples of female actors voicing discontent, both on and off stage, at class distinctions, gender segregation, endemic corruption and the myriad other issues faced by Yemeni society, this paper will demonstrate the ways in which Yemeni actresses’ unique contributions to their field have challenged cultural mores and have led to broader individual and artistic freedom for the actresses themselves.