This dissertation explores how female-born or female-bodied gender variants perform and represent their masculinities in American performance art and drag king shows. A drag king refers to a woman or female-born person who performs their gender as fluid, usually wearing masculine costumes and make-up. I focus on how race, ethnicity, and class are involved in performing female masculinities on stage, and how the intersections of other social vectors produce myriad differences in terms of stakes, styles, and forms of masculinity. I examine how female-born queer performers foreground the constructed nature of masculinity, and how they redefine established categories of gender and sexuality through performance. I argue that queer performances of female masculinities deconstruct the heteronormative gender binary and embody alternative configurations of sex, gender, class, race, and sexuality. In my first chapter, I address Peggy Shaw's Menopausal Gentleman (1997) and To My Chagrin (2003). I examine how she portrays aging white butch masculinity, sexuality, and emotion, through the reinterpretation of menopause and musings on her own whiteness. My second chapter provides a critical reading of kt shorb's [sic] of chicks, dicks, and chinks (2005) and D'Lo's Ramble-Ations (2006). Investigating the effeminization of Asian masculinity and multicultural racial performativity, I illuminate how Asian-American female masculinities are differently constituted in the interplay between class, ethnicity, diaspora, and cultural identities. In my third chapter, I analyze the 6th (Chicago, 2004) and 8th (Austin, 2006) International Drag King Extravaganza showcase performances. I describe how they reveal the theatrical nature of masculinity, and how they mark race, class, and ethnicity. In addition, I discuss how they valorize gender fluidity and multiplicity, staging queer desire and pleasure. Throughout this dissertation, by offering complex illustrations of masculine genders of the female body or the gender-ambiguous body, I contend that female-born gender variants disrupt the equation of masculinity to maleness through their theatrical performances of masculinities. I conclude that performing female masculinities can foster the critical artfulness of gender by engaging in social criticism of gender, class, race, ethnicity, and sexuality.