In April 2006, Stephen Colbert was a late-night cable-television comedian; by May, he was revered as the truth-telling jester in the farce of modern American media and politics. He delivered his speech at the White House Correspondents' Association Dinner on April 29, 2006. Although comedians and other entertainers have been invited to the annual dinner before, and while both the press and the presidency have always been open for some gentle ribbing, Colbert was the first speaker to so harshly and hilariously attack those honored institutions. As a result, Colbert found himself condemned in some circles as a tasteless bully while being venerated as a great American satirist in others. As Adam Sternbergh of New York Magazine put it:

[Colbert] wound up delivering a controversial, possibly very funny, possibly horribly unfunny, possibly bravely patriotic, and possibly near-seditious monologue that earned him a crazed mob of lunatic followers who await his every command.

Since 1914, the White House Correspondents' Association has promoted the interests of reporters whose regular assignment is the presidency. The WHCA held its first dinner in 1920, and Calvin Coolidge established a tradition when he became the first sitting president to attend the dinner a few years later. Colbert, an actor and comedian best known for his satirical television show The Colbert Report, which pokes fun at popular but often uninformed political commentators on television, was evidently invited to address the White House Correspondents' Dinner because of his popularity among younger, hipper fans.

Colbert's show regularly displays the host's earnest stance on ridiculous topics, such as his list of individuals, organizations, and even concepts that are "On Notice," which is a form of chastisement. The list of those "on notice" has included singer Barbra Streisand, the British Empire, and grizzly bears (a running joke on the show is Colbert's fear and distrust of bears). Even more daunting is the list of those people and concepts that are "Dead to Me," in Colbert's parlance. This list includes New York intellectuals, bowtie pasta, and owls. Colbert coined the term "truthiness" to describe his brand of comic hot air. "Truthiness is 'What I say is right, and [nothing] anyone else says could possibly be true.' It's not only that I feel it to be true, but that I feel it to be true. There's not only an emotional quality, but there's a selfish quality," Colbert explained in a 2006 interview with the Onion's A.V. Club. "Truthiness" was declared the Word of the Year 2005 by the American Dialect Society.

Stephen Colbert (the actor) explained the core of his show's humor to New York Magazine:

Language has always been important in politics, but language is incredibly important to the present political struggle. Because if you can establish an atmosphere in which information doesn't mean anything, then there is no objective reality. The first show we did, a year ago, was our thesis statement: What you wish to be true is all that matters, regardless of the facts. Of course, at the time, we thought we were being farcical.

In interviews, Colbert has repeatedly stressed that his TV persona is not himself but rather a character named "Stephen Colbert" who is an idiotic blowhard convinced of his own brilliance. "Stephen Colbert" is an overbearing, know-it-all jingo who takes the cotemporary culture of American politics and journalism to a ridiculous extreme. "We share the same name," Colbert says of "Colbert." "But he says things I don't mean with a straight face. On the street, I think people know the difference. But I'm not sure, when people ask me to go someplace, which one they've asked."