Jon Stewart Accepts Bill O'Reilly's Debate Invitation

The Daily Show host will debate the Fox News host Monday night

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Jon Stewart has accepted Bill O'Reilly's challenge to a debate over the if's and's and but's of the recent controversy over rapper Common visiting the White House. He will appear on The O'Reilly Factor Monday night. Possible questions that will be resolved for all time: If a rapper expresses support for an alleged cop killer should he be blacklisted from the First Lady's invitation list? And what's the big deal with Fox News devoting airtime and contributors energy digging through the lyrics of every Common song and airing the dirty ones? (The White House specifically said they didn't approve of the lyrics but felt Common's devotion to serving America's youth warranted the invite.) But why don't the lefty media care that he said bad things?! It's worth watching Stewart's rap directed at Fox News from Wednesday night to hear his point of view on these kinds of questions. O'Reilly's reply rant can be found here.

This will hardly be Stewart's first appearance on The O'Reilly Factor. His first appearance dates back to September 17, 2004 when Stewart was promoting his new book, America: A Citizen's Guide to Democracy Inaction. Right out of the gates, O'Reilly let Stewart know how scary it was that the Daily Show host might actually sort of have an influence in the outcome of the election. "You've got stoned slackers watching your show every night and they can vote! You can't stop 'em!" said O'Reilly.

O'Reilly appeared The Daily Show in 2008 and despite O'Reilly's prickly nature over the course of the previous years, Stewart praised the veteran Fox News host while the two men shared hot chocolate: "I always enjoy watching you and I do enjoy watching your program. You're not an ideologue; I'm not sure what you are.'' O'Reilly glowed. Thus was born the famous frenemy relationship the two.

After a couple more appearances on the Factor, Stewart and O'Reilly sat down for a much publicized--and later, criticized--42 minute-long conversation that aired in two segments on February 3 and 4, 2010. The conversation was heated, and the two clashed on topics ranging from blurring lines of opinion in the news to O'Reilly's role as a voice of reason. (According to Stewart, Bill O'Reilly is the "thinnest kid at fat camp.") However, as soon as Fox News posted the full, unedited interview, the network received many a scolding from bloggers for cutting out some of the more revealing parts of the interview and skewing many points in O'Reilly's favor. Not surprising, and the two hosts didn't make too big a fuss. The full interview is worth watching, but here's a clip:

Stewart appeared on The O'Reilly Factor yet again last September in the weeks before the Rally to Restore Sanity. In relating that appearance to the big ratings moment back in February, Richard Huff of the New York Post wrote simply, "Stewart makes fun of Fox on a regular basis, but he and O'Reilly are good TV." And that seems fitting. Most recently, Jon Stewart gave Bill O'Reilly a slow clap for his criticism of Donald Trump, just as O'Reilly praised Stewart for his criticism of President Obama. Conversation is sure to steer away from the Common controversy on Monday, and you can bet your britches there will be soundbytes.

This article is from the archive of our partner The Wire.