Oratory played a significant and enduring role in the public life of Frederick Douglass. This chapter charts the various eras, genres, places, topics, and traditions in which Douglass’s speaking traversed. For example, this chapter addresses Douglass’s early rhetorical education, how his contemporaries described his speaking, his connection to religion, his long career as a lecturer, the threats of violence he experienced while speaking publicly, and the array of subjects about which Douglass spoke. Such a capacious understanding of context allows for a fuller depiction of Douglass’s skill as an orator while also acknowledging his failures that are often elided from the general account of his rhetorical prowess.