On November 4, 2008, Barack Obama, an African-American man was elected as the 44th President of the United States. The election of a man of Obama's racial and ethnic background is an event of monumental social and political significance. Many Americans, both black and white, stated openly that they would never have imagined that such an election result could take place in their lifetimes, or during the lives of their children or even grandchildren. Such is the awareness of the legacy of racial hatred and injustice toward African-Americans in the United States. Ever present, that legacy was apparent in a myriad of expressions of racism throughout Obama's presidential campaign and still continues since his election. Knowledge of the social and political dynamics that emerged from the demise of African-American slavery is essential to understanding race relations in twenty-first century America. Many of the economic and social ills that have plagued the nation for generations can be traced back to the struggle for and resistance to racial equality and fair treatment. Now accessible in digitized sheet music collections of blackface minstrel music on the internet, a record of nineteenth and early twentieth century perspectives is uniquely captured through the popular music of past generations. Illuminating the political and social attitudes that led to commonly held beliefs and practices regarding African-Americans, this music has the power to help make sense of current racial dynamics and contributes to understanding the connection between meaning and context in how cultural knowledge is developed and represented.