Obama claims that The Daily Show's Jon Stewart was his toughest interview

As the White House press secretary says Stewart was Obama's most challenging interlocutor, remember some of Stewart's most pointed Q&As

At a Q&A last week at Georgetown, the White House press secretary Jay Carney admitted that, of all the interviews Barack Obama did on the road to reelection in 2012, his toughest was with The Daily Show's Jon Stewart. (We're guessing the second toughest of all time was this year's appearance on Between Two Ferns.)

This is either a sad symptom of the lackluster state of journalism, or a healthy example of the wisdom of fools; either way, it's not too surprising to those who have watched Stewart go toe-to-toe with pundits and politicians in the past. Here are just a few examples of a well-armed Stewart not just making his interviewees laugh, but challenging their public opinions and/or skewering their hypocrisy in the process.

1. Bill O’Reilly

The best frenemy in the biz, O'Reilly has been a surprisingly funny foil for both Stewart and Stephen Colbert—whose character is, of course, based in part on Papa Bear. Both O'Reilly and Stewart are playfully aware of the artifice involved in all they do, but it doesn't keep the sparks from flying. The last time O'Reilly visited TDS, the duo sparred about the President, racial profiling and gun control.
 Again, you can get a sense of how well-informed, forceful and occasionally wily Stewart can be in an extensive session:

2. Jim Cramer

One of Stewart's most hyped meetings, he took on CNBC's Mad Money host, Jim Cramer. The Daily Show host didn't pull any punches, using Cramer to represent the network and all the media outlets who aided and abetted investors and traders responsible for the financial collapse. For his part, Cramer comes off like a child called into the principal's office, pleading for clemency.

3. Alan Greenspan

When he had the former Chairman of the Federal Reserve on the show to talk about his memoir, it wasn't just a friendly review of the man's time with the government. The genuinely curious Stewart probed into the inner workings of the free market with his guest, who seemed surprised to be asked articulate questions and a little reluctant to have a conversation about difficult issues.

4. Chris Matthews

Stewart regularly leaves his set to appear on other talk shows, to speak both as a comedian and a liberal with strong opinions. From early appearances on Crossfire to spots on The O'Reilly Factor and Fox News Sunday with Chris Wallace, Stewart not only holds his own, but takes down his hosts with not just jokes but informed and passionate debate. Here, he defends his perception of Fox, his role as a comic and talks about his disappointment with the President even as he compliments Matthews's integrity:

5. Nancy Pelosi

Even when Stewart seems like he's a kitten, he makes solid points. On a recent visit to the Daily Show set, House minority leader Pelosi kept an affected smile on her face even as she faced questions about heathcare.gov and the ways in which Congress might be blind to its deficiencies.

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Editor: Marley Lynch (@marleyasinbob)


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