​Date: Nov. 13, 2008
Show: The Daily Show
Most Uncomfortable Moment: "If you go to Alabama, you're going to be killed." —O'Reilly, on the "center-right" majority of America

It's hard to blame Stewart for gloating during his interview with O'Reilly two short weeks after Obama won the Presidency. Bill plays right into Stewart's hand shortly into the interview. O'Reilly tells Stewart how fearful he is about Obama's Presidency, and Jon is ready with hot cocoa and a stuffed animal to help mollify O'Reilly.

After Bill takes his ribbing with good humor, they get into the nature of the American electorate. O'Reilly argues that America is really a "center-right" country, out of step with Obama's policies. Stewart asserts that Americans are more closely aligned with Obama. O'Reilly responds by predicting a backlash from Middle America in response to Obama's more liberal policies. Six years later, it looks like we have to give points to Bill on this one.