Holding the reins of the federal government means walking a fine line. You can't be seen as too stoic and stiff, lest you be branded as arrogant and out of touch. On the other hand, even just one moment of unfiltered goofiness could paint you as an unfocused dunce horsing around on the job. Such is the challenge facing President Obama, which Matt Bai picks apart in this week's New York Times Magazine. And Obama, contrary to his predecessors, has taken a new approach to humor in the White House. "The president, it turns out, is quite funny—and sometimes a little reckless," writes Bai.

Indeed, Obama's stuck his foot in his mouth more than a couple times, trying to lighten the mood. Before his comment last month about how a Cambridge, Mass., police officer "acted stupidly," the president made an almost squirm-worthy joke about how, if he weren't president, he'd probably be shot trying to get into the White House. That came after an incident with Jay Leno when the humorist-in-chief characterized his low bowling score as good enough for the Special Olympics. That's not to say all his jokes have fallen flat. Both the POTUS and Press Secretary Robert Gibbs have had some great one liners. ("Car and Driver named me auto executive of the year," Obama deadpanned at the White House Correspondents Dinner in May.)

Almost all past presidents have incorporated humor into their image, most often as a way to show some personality and that they could, in fact, escape the dry doldrums of Washington. But what's different about Obama, writes Bai, is that he finds such stagecraft and the falsity of modern politics to be as laughable as everyone else does. It's as if, by risking a tiny amount of political capital, he's poking fun at an over-the-top reverence toward the office. In that assessment, Bai just speculates. But it's almost blindingly clear that in the Obama White House, humor is an end, not just a means to a political goal—even if it does sometimes get you in trouble. Just ask Joe Biden.