10 Times Jon Stewart Outdid Journalism

From Charleston to class warfare and ripping CNN a new one, this was the 'Daily Show' host at his best

Kathleen Sebelius on Obamacare

When U.S. Health and Human Services Secretary Kathleen Sebelius appeared on The Daily Show October 7, 2013, her job was to do damage control: The recent roll-out of the Obamacare website had been a glitch-y disaster, and it was critical that she assure Stewart's young audience that the Administration knew what it was doing. Instead, she bombed, awkwardly oscillating between patronizing laughter and vague, unhelpful answers in the face of Jon's objections to the Democratic leadership's organizational incompetence and deeply flawed healthcare reform. "It's better today than it was yesterday, and it will keep getting better," Sebelius spouted near the end, her cheery words sounding like such an unconvincingly hollow sound bite. Stewart couldn’t even mask his smirking doubt: "I hope things work out," he told her. It didn't for Sebelius: Six months later, she resigned. TG

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