10/04/2011 12:43 pm ET Updated Dec 06, 2017

Stephen Colbert Stumps Jeffrey Toobin Over Supreme Court (VIDEO)

Stephen Colbert baffled New Yorker writer and CNN legal analyst Jeffrey Toobin on his show Monday night when discussing the upcoming Supreme Court case on the legal mandate requiring individuals to purchase health care.

A federal judge in Pennsylvania ruled that requiring individuals to purchase health care insurance is unconstitutional, propelling the case to the Supreme Court to settle. Colbert proved that he might be just as skillful as some of our most trusted cable news analysts by simply asking Toobin when the government mandates citizens to purchase, well, anything.

According to Toobin, the "government tells you to do all sorts of things," including sometimes telling you to purchase certain items. An exasperated Colbert shrieked, "when!?"

"Um...not often," Toobin sheepishly answered after a short pause.

"Well hold on, legal analyst! Checkmate!" Colbert retorted. He quickly admitted, however, that he had pulled this argument "out of my ass."

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