This purpose of this dissertation is to utilize womanism and ratchetness to determine how the actions of Tyler Perry’s Madea and Christianee Porter’s Miss Shirleen characters represent Black women’s agency through their ratchet actions. This dissertation analyzed two Tyler Perry films and five Miss Shirleen videos to determine whether their actions conveyed cultural and liberative significance beyond entertainment. This research discovered that both characters engaged in resistance to disempowering narratives through actions that embraced a radical subjectivity and subsequent dismissal of respectability politics that embraced the strengths of Black womanhood in affirming, creative, and audacious ways. This dissertation also found that ratchetness and womanism as liberative agency leave room for Black women to redefine themselves and evolve based on their own indigenous knowledge and create a language that is familiar and uplifting for themselves. Moreover, Black women can be ratchet, womanist, and respectable simultaneously regardless of class status thereby rejecting a pathologized Black womanhood.