New Orleans native Lil Wayne began his professional career in rap music at the age of eleven. Since then, he has garnered sixty-four number one hits on the Billboard hot 100 chart, the most ever by a rapper. Lil Wayne is among the most controversial artists of the dirty South hip hop scene, which has been accused of creating the most overtly problematic and self-degrading images in hip-hop culture. This document seeks to examine Lil Wayne in the context of these criticisms and controversies. Looking at the broader paradigms of Southern hip hop musical style, lyrical subjectivity and visual imagery, my hope is to reveal a certain complexity in Lil Waynes gestures of identity construct. It is not my goal to defend or justify Lil Waynes actions, but merely to complicate the reductive view of Southern hip hop as obtuse and destructive for the sake of enabling further scholarly conversation.