Gender and sexuality is a controversial theme in Tupac’s music. There is no clear classification of his music based on his view of women and sexuality. From one point of view, Tupac can be described as a person who adores and respect women, and from another view; he is a wicked person who has no respect for women. It easy to understand why Tupac fits into both extremes based on a closer look at his personal life. He had a double-edged personality; as a person of high moral standards advocating for the right of less fortunate black Americans, adored by thousands of Black American youths, on the other extreme, he is an outcast, living a thug life, fighting the system and always on the wrong side of the law, all this aimed at personal glorification. In his best-selling book on Tupac’s life, ‘Holler when you see me’ Michael Dyson notes the conflicting personality portrayed by Tupac through his music, he writes this about the artist ‘Tupac has torn his entire short life about what he wanted and expected from women. If his heart was bruised at 17 because of the bad-boy archetype trumped his nice-guy image, he vigorously compensated for its defeat in the few years he had remaining’ Dyson also notes this on Tupac rap music ‘In his haunting voice can be heard the buoyant hopefulness and the desperate hopelessness that mark the outer perimeters of the hip-hop culture he eagerly embraced, as well as the lives of the millions of youth who admired and adored him’. During his short life, Tupac’s music career was a success. He has sold the highest number of records in rap music history, during and after his death. His first successful single, “Brenda’s Got a Baby” was the first song where Tupac addressed issues relating to women. In the song, Tupac is crying out for the sake of a young girl going through lots of crises in a society that does not seem to recognize the pressing needs of young women. The young girl, Brenda, is helpless with no parental support as Tupac informs to us that young girl ‘ never really knew her moms and her dad was a junky…………the girl can hardly spell her name, that’s not her problem; that up to Brenda’s family….’ It is important to note that in this song, Tupac does not use any undignified words towards women. He is the perfect Tupac who adores and supports women going through a crisis. “Keep yah Head Up” is another inspirational song to black women, it is a call for black women to stand firm and believe in themselves and not allow men to put them second in the social order. He advises women to “Forgive but don’t forget, girl keep ya’ head up, and when he tells ya’ you ain’t nothin’, don’t believe him’ . Tupac’s past life and seeing her mother go through an abused relationship with men influenced greatly the writing of this song. Dyson writes in his book ‘ Tupac conjures an image (about women) from his recent past, lamenting the mistreatment of young women by his male counterparts. According to Dyson, “ In black America, mother love is second only to the love of God – but just slightly in the song,” Tupac exemplifies Michael Dyson stand through his song ‘Dear Mama’. In this song, we again encounter a Tupac who understands the plight o