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How Jon Stewart became President Obama’s biggest problem

President Obama's biggest problem when it comes to selling the American public on the so-far rocky rollout of his health-care law isn't John Boehner or Mitch McConnell or even Ted Cruz. It's Jon Stewart.

HANDOUT IMAGE: Jon Stewart. Indecision 2006 -- "Battlefield Ohio: 'The Daily Show's' Midwest Midterm Midtacular"

Stewart, the host of the wildly popular "Daily Show" on Comedy Central, has emerged as a harsh critic of and the Obama administration's inability to fix it.

Stewart dedicated the entire first 10 minutes of his show -- three full segments -- on Monday to slashing hits on the Web site and the president's handling of the problems.  He compared Obama to "Gil," the hapless salesman from "The Simpsons," showed "Daily Show" correspondent John Oliver stuck in a computer after trying to sign up for Obamacare and expressed amazement that even the calculator on the Web site doesn't work. (And, remember, Stewart was heavily critical of Health and Human Services Secretary Kathleen Sebelius during an appearance on his show earlier this month.)

Here's a clip from Monday that captures Stewart's critique (it may not be safe to play at work for some of you):

Who cares what a late night comedian/talk show host thinks? President Obama should if viewership details on Stewart's show are right.

According to a 2012 Pew Research Center poll, "The Daily Show" has the second-largest share of young viewers -- aged 18-29 -- of any of the 24 media outlets tested. (The only one with a higher number of young viewers was the "Colbert Report.")

Image courtesy of Pew Research Center

President Obama and his administration have made it quite clear that one of the big beneficiaries of the law should be young people. "Already, millions of young adults have been able to stay on their parents’ plans until they turn 26," Obama trumpeted in a speech defending the Affordable Care Act on Oct. 1. On Monday, in an address designed to calm worries about the problems with the Web site, Obama specifically referenced three young people standing behind him who had been able to stay on their parents' insurance until they were 26 and added: "Millions of other young people are currently benefiting from that part of the law."

But, these same young people tend to get much of their news -- and therefore have their opinions shaped -- not by places like The Washington Post or the CBS Evening News but rather by Stewart. He is their Tom Brokaw, their David Brinkley. So, what Stewart says matters -- a lot.

How might Obama solve his "Stewart" problem? Maybe appear on the show -- as he has done six times before, including twice as president. Stewart would, undoubtedly, challenge Obama on the problems with the site but would also give the president a platform by which he could address the growing public perception that the law (or at least the Web site) just isn't working.

Chris Cillizza writes “The Fix,” a politics blog for the Washington Post. He also covers the White House.

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