Jon Stewart's greatest 'Daily Show' interviews

Feb. 11, 2015 2:31 PM PT

On “The Daily Show,” Jon Stewart can make any celebrity promotional appearance fun with his laid-back shoot-the-bull style. But occasionally, his full intellect is engaged, most generally by interviewing someone from the political sphere. Or an author. His guest list runs the gamut. And more so than many late night hosts, he always seems prepared. Not just with questions, but with follow-ups and facts, so as not to get bulldozed by bull.

With Stewart stepping down from the Comedy Central show at some point later this year, now’s as good a time as any to look back on some of Stewart’s best moments, not as political and media satirist, but as one of the best short-form interviewers on TV.

FULL COVERAGE: Jon Stewart on ‘The Daily Show’ and beyond

Stewart screams at Jim Cramer

In the wake of the financial meltdown of 2008, Stewart directed a lot of ire toward CNBC financial guru Jim Cramer, whose show “Mad Money,” along with his network, Stewart saw as a dishonest booster of the stock market at the cost of many people’s life savings.

When he finally had Cramer on as a guest in March 2009, Cramer was no doubt expecting a jokey, perhaps a little serious discussion. Instead, it was a full-on dress-down, with Stewart’s anger at Cramer taking over parts of the interview.

What’s remarkable about the segment is how ill-prepared Cramer was to defend himself against Stewart’s rage.

Like all the great “Daily Show” interviews, this one went too long to air on TV in its entirety. But the “extended interview” is still available online here.

Stewart calls President Obama “dude”

Barack Obama appeared on “The Daily Show” five times, dating back to before he was even president. Interviewing world leaders on a regular basis surely left Stewart feeling at ease in their presence, but during Obama’s appearance just before the midterm election in 2010, Stewart’s familiarity with him may have crossed a line the commander in chief didn’t want crossed.

While defending his track record on the economy, Obama said, “We saved the taxpayers a whole lot of money, and, and in fairness, Larry Summers did a heck of a job, trying to figure out, how to -- .” Stewart interrupted, “You don’t wanna use that phrase, dude.”

Stewart was referring to George W. Bush’s use of the phrase “heck of a job” to characterize the performance of FEMA Deputy Director Michael Brown in the aftermath of Hurricane Katrina in New Orleans.

“Pun intended,” Obama said, to laughter.

However, many felt Stewart may have been a tad disprespectful with the use of the word “dude.” Even he admitted later that Obama didn’t appear to enjoy being called that. Next time, perhaps it’s better to stick to “Mr. President.”

Here‘s the exchange in question.

Stewart argues with John McCain

Sen. John McCain was one of the most frequent guests on “The Daily Show” in the early ‘00s, second only to Brian Williams, but during an interview in 2007 things got a little heated between the senator and Stewart.

McCain and Stewart launched into a debate over the Bush administration’s policy in Iraq, but when the disagreement swung around to the notion of supporting the troops, Stewart got angry.

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“All I’m saying is you cannot look a soldier in the eye and say questioning the president is less supportive to you than extending your tour for three months when you should be coming home to your family,” he said to a McCain who struggled to get a word in.

McCain has appeared a couple of more times on “The Daily Show,” most recently in 2008. But he’s no longer as frequent a guest.

The argument happens here.

Stewart is charmed by Malala Yousafzai

He’s a master of working big names, but occasionally Stewart books a guest like Malala Yousafzai, whose activism for human rights and women’s education in her home country of Pakistan got her shot, but also won her a Nobel Peace Prize. She was the youngest-ever winner at age 17.

Her appearance on “The Daily Show” in October 2013 caused Stewart to go momentarily speechless when she articulated her argument for methods of peace in the face of danger from Taliban gunmen.

After a pause, Stewart replied, “I know your father is backstage and he’s very proud of you, but would he be mad if I adopted you? Because you sure are swell.”

The interview can be seen here.

Stewart vs. O’Reilly in 11 parts

Fox News host Bill O’Reilly and Stewart couldn’t be further apart politically, yet there’s a certain admiration the two have for each other. That back and forth gives their discussions a snap and giddiness not often seen. You may think Stewart is a liberal wet blanket or O’Reilly a conservative blowhard, but together they make magic.

Take your pick of any of O’Reilly’s appearances over the years, dating all the way back to 2001.

Follow me on Twitter: @patrickkevinday

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