Satire is notoriously difficult to do well.  If anyone doubts that, just ask Esquire, which might face a lawsuit for libel over its clumsy attempt to skewer WND this week on the birth-certificate controversy, although I share James Taranto’s skepticism that the case will succeed.  Even those who make a successful career out of satire, like Stephen Colbert, they eventually miss badly as well when their stunts backfire.  The Wall Street Journal explains how Colbert started off trying to skewer the Supreme Court over the Citizens United v FEC ruling, and ended up getting a lesson in its necessity:

Comedy Central funnyman Stephen Colbert, like most of his friends and allies on the left, thinks that last year’s Supreme Court ruling in Citizens United v. FEC is, literally, ridiculous. To make his case that the ruling invites “unlimited corporate money” to dominate politics, Mr. Colbert decided to set up a political action committee (PAC) of his own. So far, though, the joke’s been on him.

The hilarity began last month, when Mr. Colbert began to have difficulty setting up his PAC, which is a group that can raise money to run political ads or make contributions to candidates. So he called in Trevor Potter, a former Federal Elections Commission (FEC) chairman who is now a high-powered Washington lawyer.

Mr. Potter delivered some unfunny news: Mr. Colbert couldn’t set up his PAC because his show airs on Comedy Central, which is owned by Viacom, and corporations like Viacom cannot make contributions to PACs that give money to candidates. As Mr. Potter pointed out, Mr. Colbert’s on-air discussions of the candidates he supports might count as an illegal “in-kind” contribution from Viacom to Mr. Colbert’s PAC.

That didn’t quite work out, either:

On May 11, Mr. Potter returned with more bad news: Viacom didn’t like Mr. Colbert’s plan because his on-air commentary might still amount to a contribution from Viacom to his Super PAC. It’s difficult to place a dollar value on airtime, so a reporting mistake could put both Viacom and Mr. Colbert in legal hot water. Isn’t campaign-finance law funny?

“Why does it get so complicated to do this? I mean, this is page after page of legalese,” Mr. Colbert lamented. “All I’m trying to do is affect the 2012 election. It’s not like I’m trying to install iTunes.”

Well, that’s pretty much what the nonprofit group Citizens United said to the Supreme Court in the case that Mr. Colbert is trying so hard to lampoon.

Indeed.  Colbert can thank Congress for the “page after page of legalese” concerning political contributions, especially the McCain-Feingold Act that the Supreme Court partially struck down in the Citizens United ruling.  That ruling, in practice, does not allow for corporations to run the debate, at least not without navigating a minefield of regulations that the FEC itself can’t effectively manage.  They routinely take months to settle disputes, usually after elections when the issues that triggered the intervention are made moot.

In fact, as the WSJ notes, the existing legal labyrinth is so daunting that Colbert has now applied for a special waiver to conduct political speech.  I’m not sure that’s what the founders had in mind when they wrote the First Amendment, but I do believe that it’s the best possible satire Colbert could have created from his efforts — and it’s in the exact opposite direction of what he set out to prove.