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5 of Jon Stewart’s funniest, harshest, most memorable takedowns

Rick Kern/Getty Images for Comedy Central

Nobody feuds like Jon Stewart, and his takedown segments on The Daily Show, usually of other TV media personalities, have been some of his most popular and memorable moments. But they weren’t just funny — they were part of his larger, deadly serious criticism of American TV media and its failings.

Now that Stewart has announced he will leave The Daily Show, here are a few of his most cutting, and best-known, takedowns. If you watch nothing else, skip down to the Karl Rove segment (number five) and watch what Stewart does on Fox News’ treatment of women in politics, maybe one of his most famous segments.

1) Glenn Beck

What made the 2011 takedown of Glenn Beck so epic was that Stewart broke with his usual routine — show a clip of his target being absurd, make a silly face, crack some jokes. Instead, he launched into an impression of Beck and his famously conspiratorial Fox News show that lasted more than half of the night’s episode. Here it is:

2) Rick Sanchez

While Stewart got the most mileage out of Fox News, he seemed just as irate, or even more so, with CNN, which he saw as biased in its own way, but toward sensationalism and superficiality, over one party or another. Here, he went after Rick Sanchez after the CNN host called Stewart “a bigot”; that aspect gives the segment an added dimension, but it’s really of a piece with Stewart’s larger criticisms of CNN.

3) Jim Cramer

In March 2009, as part of its coverage of the US financial downturn, Stewart criticized the financial network CNBC and accused it of providing shoddy advice to its viewers, particularly when it came to downplaying the failings, poor financial health, or irresponsibility of major banks. The critical coverage sparked an open feud with CNBC and particularly with marquee anchor Jim Cramer, which became a minor media story and culminated in Cramer appearing, awkwardly, on the show.

Here’s the initial segment that sparked it:

And here’s a segment focusing on Cramer specifically; it features Stewart at his feudiest:

4) Bill O’Reilly

There was a bizarre, almost frenemy nature to Jon Stewart’s relationship and feud with Fox News host Bill O’Reilly; the two would attack one another on their shows, but also occasionally appear on each other’s show as guests. The interviews were captivatingly awkward, as both tried to convey a cool, above-it-all good humor while getting in as many shots as possible. Here’s one of O’Reilly’s appearances on The Daily Show:

Still, the real meat of the feud came when they were safely ensconced across town from one another and could take shots freely. Here’s just one of Stewart’s many bits poking at the Fox News host:

5) Karl Rove (and really Fox News generally)

Okay, Rove is more political operative than media figure, but at the moment of this 2008 segment he was primarily known as a talking head (in this case, cheering on Sarah Palin’s vice presidential nomination). And, in any case, it’s just too good of a segment not to include, especially when Stewart turns to Rove’s and Fox News’ hypocrisy on gender and sexism — which completely changes based on whether the woman they’re discussing is or is not a major Republican politician.

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