During the 1980s, Cosby produced and starred in one of the decade's defining cultural products, The Cosby Show, which aired from 1984 to 1992 and featured an upper-class African-American family without resorting to the kinds of vulgar stereotypes previously seen among African-American characters in prime-time television. While some argued that The Cosby Show ignored the issues of racial inequity still prevalent in society, many agreed that it showcased positive role models.

The late 1990s and early 2000s brought trouble for Cosby, first in early 1997 with the death of his only son, Ennis, who was shot to death on a Los Angeles freeway in a random act of violence. Also that year, he was dragged into a court case that involved a young woman who was charged with extortion in claiming that he was her biological father - a shocking accusation that Cosby denied. Cosby admitted to having a one-time affair with the woman's mother.

Despite these personal setbacks, Cosby did not slow down at all in the 1990s, starring in Cosby, which first aired in 1996, and hosting Kids Say the Darndest Things, which began in 1998, as well as making more movies. He has also continued appearing on the stand-up circuit, delighting audiences with his gentle, paternal brand of comedy. His material consists mainly of anecdotal tales, often dealing with his upbringing and raising his own family, and he is known for having a clean, kid-friendly routine. His good-natured, fatherly image has made him a popular personality and earned him the nickname of "America's Black Dad," and he has also been a sought-after spokesman for products like Jell-O Pudding and Coca-Cola.