Ishmael Reed`s Flight to Canada and Toni Morrison`s Tar Baby share the theme of black liberation. Set in America under slavery, Reed`s Flight to Canada is a narrative of Raven Quickskill who runs away from his master to Canada, the land of freedom. Set in contemporary America, Morrison`s Tar Baby dramatizes the tension between Jadine Childs and Son Green who respectively designate the site of postcolonial black identity in urban white culture and ancestral black culture. However, Reed and Morrison do not envisage the vision for true emancipation through those central characters that step outside of their oppressive reality. In Reed`s Flight to Canada, Raven Quickskill never reaches the land of freedom. In Morrison`s Tar Baby, Jadine and Son fail to locate the site where black people can be culturally and spiritually decolonized and free from racial ideologies. It is through Uncle Tom-ish characters in the underlying narrative that Reed and Morrison illuminate the possibility of achieving true freedom. Uncle Robin in Flight to Canada and Sydney in Tar Baby, apparently corresponding to the Uncle Tom figure in Harriet Beecher Stowe`s Uncle Tom`s Cabin, never leave their oppressive reality and remain faithful to their master. However, they surreptitiously mock/challenge the master`s authority and transform their oppressive reality into the site of liberation by taking advantage of the colonial situation where the mastership is maintained by the service and labor of black slaves. Thus, Uncle Robin and Sydney show that black people can achieve true liberation without ever leaving the oppressive ground. Ultimately, Reed`s Flight to Canada and Morrison`s Tar Baby imply that black liberation should be sought and fought right inside their oppressive reality without totalizing the ground.