Jon Stewart's recent interview with former Vice President Al Gore — in which the comedian grilled the famed environmentalist over his controversial sale of Current TV to Al Jazeera, which is backed by big oil money — got tongues wagging for how aggressively Stewart went after Gore. But it was hardly The Daily Show host's first hard-hitting interview. Here are some of Stewart's best sitdowns-turned-takedowns:
1. Jim Cramer
The near collapse of the economy in 2008 — and the subsequent bailout of Wall Street — gave plenty of people a reason to pop a blood vessel or two, and Stewart tapped into that anger by going after one of Big Finance's chief media champions: CNBC. Stewart soon turned his attention to the network's most famous face, Jim Cramer, host of Mad Money, who he accused of publicly suggesting that investors put or keep their money in Bear Stearns before its massive collapse. The segment touched off a brief war of words between Stewart and Cramer, and eventually, Cramer agreed to appear on Stewart's show. Stewart and his crew dug up a rather damning piece of footage in which Cramer explained how people like him can alter the system for their gain, prompting Stewart to plead: "I want the Jim Cramer on CNBC to protect me from that Jim Cramer." Cramer says he still feels the sting from the interview to this day.
2. President Obama
In this 2012 interview, Stewart wasted no time roasting the president for his poor first-debate performance against GOP contender Mitt Romney, contrasting two photos of First Lady Michelle Obama's reactions following two of the showdowns and asking him, "Do you know which debate was which?" Stewart also wryly called out the Obama campaign's increasingly negative stance by asking the president, "Do you feel you have a stronger affirmative case for a second Barack Obama presidency or a stronger negative case for a Romney presidency?" — a serious question that also got a smattering of laughs from the audience.
3. Grover Norquist
The way liberals see it, Grover Norquist, the president of Americans for Tax Reform and author of the infamous "Pledge," which forbids any legislator who signs it from ever raising taxes, has become one of the main obstacles in Congress' never-ending battle to accomplish, well, anything that has to do with money. Stewart's interview with Norquist was a verbal fencing match in which the two men each used the other's words to thrust and parry, including when Norquist explained that his pledge was just the first step and that it would be effective if legislators also stopped spending so much money. Stewart shot back, "But where's that pledge? The first pledge is easy. Anybody will sign that."
4. Bill O'Reilly
Stewart and O'Reilly have become something of a comedy duo as they've squared off over the years to discuss the issues of the day on each other's shows. They often manage to have intelligent discussions about complex issues (how intelligent depends on your political point of view or who you're rooting for). One of their earliest interviews came just after President Obama's first win for the White House. Stewart called out O'Reilly and his fellow Fox News pundits for playing the fear card, handing O'Reilly hot cocoa and a teddy bear named "Mr. Snuggles" to help him get over his "fear of governance." The two then exchanged jovial barbs and jabs over the Iraq War, the progression of gay marriage, and the true political center of the nation.
5. Paul Begala and Tucker Carlson
During a legendary 2004 appearance on the now-defunct CNN debate show Crossfire, Stewart — a guest in this case, not the host — eviscerated Crossfire's black-and-white approach to debate. When Carlson accused Stewart of not being hard enough in his questioning of presidential contender John Kerry leading up to the 2004 election, Stewart "cross-fired" saying (around the 4:43 mark), "It's interesting to hear you talk about my responsibility. I didn't realize that and maybe this explains quite a bit that the news organizations look to Comedy Central for their cues on integrity." The segment went viral on YouTube and Crossfire was canceled just a few months later.
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