30 most scorching Jon Stewart takedowns of Republicans

4 of 31
The Daily Show (Comedy Central)
The Daily Show (Comedy Central) /

28. Stewart takes on Bill O’Reilly over “white privilege”

After the widely covered tragic shooting death of an unarmed eighteen year old black man named Michael Brown in Ferguson, Missouri, the incident quickly became the hottest topic in politics. As a white police officer killed Brown, the issue of race was brought up, with many talking about “white privilege”— the idea that whites don’t have to endure nearly as much hassle in the United States as African-Americans do.

Bill O’Reilly used this situation as an opportunity to rebuke the concept of white privilege on his show, suggesting that it’s made up only to further the political agenda of liberals and progressives. He stuck by this argument when he appeared on The Daily Show to promote his new book, and Jon Stewart definitely wasn’t having it.

Stewart asked O’Reilly about his upbringing in Kentucky, and O’Reilly agreed that he had a wonderful childhood there. When asked if black people could have lived peacefully in his home town, O’Reilly said, “Not at that time.”  That gave Stewart the perfect chance to prove his point, which would cause O’Reilly to concede his argument, by firing right back at him:

“So that, my friend, is what we call in the business ‘white privilege’.”

Next: 27. Don't act so surprised