‘Daily Show’: Jon Stewart’s 5 Best Political Interviews

Comedy Central

This story first appeared in the Sept. 12 issue of The Hollywood Reporter magazine.

Jon Stewart, a liberal darling, makes a point of challenging guests from across the ideological spectrum. Here are five of his most memorable interview with political figures from The Daily Show.

President Obama — Oct. 18, 2012
Stewart opened the interview by skewering Obama for his woeful debate performance against Republican Mitt Romney two weeks earlier and went on to grill him about the campaign's increasingly negative tone.

Sen. John McCain — April 4, 2006
A confrontation with McCain about his rightward shift, including his decision to appear at Jerry Falwell's Liberty University after McCain previously had denounced Falwell as an "agent of intolerance."

Grover Norquist — March 12, 2012
Stewart challenged the Tea Party favorite on his Taxpayer Protection Pledge — a promise to vote against any tax increases, signed by a vast majority of Republicans in Congress — labeling it as "pandering."

Al Gore — Jan. 30, 2013
Stewart questioned the self-proclaimed environmentalist's motivations for selling his cable network Current for $500 million to "fossil fuel-backed" buyer Al-Jazeera, owned by the oil-wealthy emirate of Qatar.

Hillary Clinton — July 15, 2014
Mixing it up with the presumptive 2016 presidential contender, Stewart grilled her on Israel's military action, her comments about being "dead broke" when she and President Clinton left the White House and whether she's actually running.