Born October 12, 1932 in St. Louis, Gregory spent his childhood shining shoes in order to help feed his family; in high school, he made headlines for leading a march against scholastic segregation. After pursuing a career in comedy, Gregory consciously avoided falling prey to the stereotypes common among black comics; his material avoided excessive use of obscenities, and while he dealt heavily with issues of race, his observations were sharp and trenchant, never silly or toothless. Gregory's goal was to reach white audiences as well as black, and from the outset, he steeled himself against the racism he was bound to face; according to legend, he prepared for the expected racial epithets by planting his wife in the audience and forcing her to randomly yell out "Nigger!," to which he would have to fire off a suitable comeback.

Gregory first recorded for Colpix (including his 1961 debut In Living Black and White), but soon signed to the Vee-Jay label and issued Dick Gregory Talks Turkey, a collection of topical observations highlighting the comedian's agile, ironic delivery. Two more records followed -- Two Sides and the prophetically titled Running for President -- before Gregory made his first overt steps towards social activism with the album My Brother's Keeper, a benefit record to help feed the poor in LeFlore County, MS. After the county's Board of Services told the community that they could not raise the $37,000 necessary to fund the area food bank, Gregory privately pressed 3,700 copies of the LP, which he sold for $1.60 each to arrive at the necessary total. (The remaining proceeds paid off production costs.)

Although Gregory continued his busy performing schedule, his social and political aspirations continued to grow; after signing to Colpix and releasing the albums East & West, We All Have Problems, and the 1961 Top 25 hit In Living Black and White, he retired from standup to focus on running in the 1968 presidential election. Inspired by Martin Luther King, Jr., Gregory also became an ardent anti-war activist, and fasted in response to human rights abuses both at home and abroad. When he finally returned to comedy in 1969 with the LP The Light Side: The Dark Side, his outlook was significantly altered; although still sly and witty, his routines took the form of lectures, complete with cautionary messages for the audience to ponder.

After another tenure as a performer which yielded records like 1970's Live at the Village Gate, 1971's Dick Gregory On..., and 1972's Kent State, Gregory again retired from the club stage, this time for more than two decades; Caught in the Act, his final record, captured his farewell performance from August, 1973. In subsequent years he remained a committed activist and a popular public speaker, but perhaps more famously, he earned recognition for his diet plan promoting the virtues of a vegan raw food diet. In 1992, Gregory also founded the "Campaign for Human Dignity" movement to help battle crime in his native St. Louis; by 1995, he finally returned to standup comedy, performing the occasional live date.