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Politics and views

Cosby received an award at the celebration of the 50th-anniversary commemoration of Brown v. Board of Education ruling—a ruling of the U.S. Supreme Court that outlawed racial segregation in public schools. Later, in May 2004, he made public remarks critical of African Americans who put higher priorities on sports, fashion, and "acting hard" than on education, self-respect, and self-improvement. He pleaded for African American families to educate their children on the many different aspects of American culture. In the Pound Cake speech, Cosby asked that African American parents teach their children better morals at a younger age. As reported in The Washington Times, Cosby "told reporters during a special session of the Congressional Black Caucus Foundation 's 34th annual legislative conference parenting needs to come to the forefront. If you need help and you don't know how to parent, we want to be able to reach out and touch you." Richard Leiby of The Washington Post reported, "Bill Cosby was anything but politically correct in his remarks Monday night at a Constitution Hall bash commemorating the 50th anniversary of the Brown v. Board of Education decision."

Cosby was again criticized, and was largely unapologetic, for his stance when he made similar remarks during a speech at a July 1 meeting of the Rainbow/PUSH Coalition that commemorated the anniversary of Brown v. Board, where he said: "... you've got to stop beating up your women because you can't find a job, because you didn't want to get an education and now you're minimum wage." During that speech, he admonished blacks for not assisting or concerning themselves with the individuals who are involved with crime or have counterproductive aspirations. He further described those who needed attention as blacks who "had forgotten the sacrifices of those in the Civil Rights Movement ".

In 2005, Georgetown University sociology professor Michael Eric Dyson wrote a book, Is Bill Cosby Right? Or Has the Black Middle Class Lost Its Mind? In the book, Dyson wrote that Cosby was overlooking larger social factors that reinforce poverty and associated crime; factors such as deteriorating schools, stagnating wages, dramatic shifts in the economy, offshoring and downsizing, chronic underemployment, and job and capital flight. Dyson suggested that Cosby's comments "betray classist, elitist viewpoints rooted in generational warfare". However, Cornel West defended Cosby and his remarks, saying: "He's speaking out of great compassion and trying to get folk to get on the right track, 'cause we've got some brothers and sisters who are not doing the right things, just like in times in our own lives, we don't do the right thing... He is trying to speak honestly and freely and lovingly, and I think that's a very positive thing."

In a 2008 interview, Cosby mentioned Philadelphia; Atlanta; Chicago; Detroit; Oakland, California; and Springfield, Massachusetts among the cities where crime was high and young African American men were being murdered and jailed in disproportionate numbers. Cosby stood his ground against criticism and affirmed that African American parents were continuing to fail to inculcate proper standards of moral behavior. The Obama presidency had the potential to affect television shows, but people had differing reactions to that. After Barack Obama was elected president, Cosby said he was "not all that optimistic that Obama’s presidency will make a major difference in terms of onscreen diversity," saying "they would die before putting another show on about a black family and black pride."

Cosby has also been critical of conservative Republican politicians in regard to their views on socioeconomic and racial issues. In a 2013, CNN interview regarding voting rights, Cosby stated "this Republican Party is not the Republican Party of 1863, of Abraham Lincoln, abolitionists and slavery, is not good. I think it's important for us to look at the underlying part of it. What is the value of it? Is it that some people are angry because my people no longer want to work for free?" Cosby's social commentary led to the unsealing of documents in a previous civil suit by a woman who had accused Cosby of sexual assault, which in turn sparked renewed interest in older allegations. The judge ruled that releasing the sealed documents was justified by the "stark contrast between Bill Cosby, the public moralist and Bill Cosby, the subject of serious allegations concerning improper (and perhaps criminal) conduct".