Stewart, a normally friendly interview for Democrats, has been one of the Obamacare rollout's foremost critics. At one point on Thursday night, he laughed when Pelosi told him that she didn't know why HealthCare.gov, the federal health exchange site, was so badly botched.

"Why is it so hard to get a company to execute that competently?" Stewart said, part of a line of questioning that focused on why government competency looks so absent to the outside observer.