Political pundit Bill O'Reilly last appeared on Jon Stewart's The Daily Show on November 13, 2008. Prior to his post-election appearance in 2008, O'Reilly appeared on The Daily Show in 2004.Pioneer Times: Political Comedy Shows (November 10, 2008)

In O'Reilly's November 2008 appearance on The Daily Show, Jon Stewart tried to soothe O'Reilly's "fears" of a Barack Obama administration by providing him with hot cocoa with marshmallows and a small teddy bear named Mr. Snuggles. O'Reilly claimed that the United States was a "center right" country and joked that Stewart would be "killed" if he went to Alabama. When O'Reilly claimed that conservatives wanted to uphold "tradition" in America, Stewart countered by saying that granting the right of gay marriage was part of a deeper progressive tradition in the nation.The Huffington Post: Obama Fears, The Secular Revolution And A Teddy Bear (November 14, 2008)

In 2004, when Jon Stewart appeared on The O'Reilly Factor, O'Reilly referred to Stewart's audience as "stoned slackers". In the months that followed, several studies were released suggesting that viewers of The Daily Show were actually better educated and more knowledgeable about current events than viewers of The O'Reilly Factor.MSNBC.com: 'Stoned slackers' watch Jon Stewart? Stewart referenced this point on his show and joked about it when O'Reilly appeared on The Daily Show in 2004.Milk and Cookies: "Stoned Slackers" on The Daily Show

• "The tradition of America is a progression of individual freedoms. You know what the tradition of America would say: Gay marriage is the next step in the progression of America. That's the tradition of America. You're misrepresenting the tradition."—Jon Stewart, 2008The Huffington Post: Obama Fears, The Secular Revolution And A Teddy Bear (November 14, 2008)

• "The whole federal government frightens me. There isn't anything about it I like... I'm an anarchist - Power to the people."—Bill O'Reilly, 2008The Huffington Post: Obama Fears, The Secular Revolution And A Teddy Bear (November 14, 2008)

• "If you go to Alabama, you're going to be killed... they'll stone you to death."—Bill O'Reilly, 2008The Huffington Post: Obama Fears, The Secular Revolution And A Teddy Bear (November 14, 2008)

• "You know what's really frightening? You (Jon Stewart) actually have an influence on this presidential election. That is scary, but it's true. You've got stoned slackers watching your dopey show every night and they can vote."—Bill O'Reilly, 2004CBS News: Bill O'Reilly Vs. Jon Stewart (September 28, 2004)

• "If Bill O"Reilly needs to have an enemy, needs to feel persecuted, you know what? Here's my Kwanzaa gift to him. Are you ready? All right. I'm your enemy. Make me your enemy. I, Jon Stewart, hate Christmas, Christians, Jews, morality, and I will not rest until every year families gather to spend December 25th together at Osama's homo-abortion-pot-and-commie-jizzporium."—Jon StewartMedia Matters: Stewart Responds to O'Reilly's Misleading Attack (December 8, 2005)