This book is a generic comparison between the confessional poet Anne Sexton and the rapper Eminem. Both artists have much contributed to music and literature as Sexton won The Pulitzer Prize and Eminem has won countless Grammy and other Awards. The interest in relating literature to music has been a debatable topic as people disagree if music, especially rap, is worthy of comparison with literary works. But including marginalized genres and popular culture can be a fruitful act. This study questions rap's literariness and the blurring of boundaries between poetry and rap. Sexton and Eminem write in a similar confessional autobiographical style. But they blur the lines between the poet and the speaker. Their personal suffering are a source of inspiration in tackling universal themes. Confessional poetry and rap share a postmodernist style and fuse different elements such as the real with the fictional. Equally important, they are highly linked via their performativity. Sexton recorded CDs and performed her poetry on stage. Rap can be seen as a modern reinvention of confessional poetry. It is, thus, possible to consider rap a modern literary genre that can be used in classrooms.