Stephen Colbert’s Greatest Moment

‘Truthiness’ will out.

As Stephen Colbert leaves Comedy Central to take over for David Letterman (and take on The Jimmys of late night), it’s worth looking back at the moment when America’s foremost fake pundit first exercised his full promise. It was 2006, President George W. Bush was in office, and Mark Smith, the outgoing president of the White House Press Corps Association, had decided it might be edgy to have Jon Stewart’s apprentice perform at the White House Correspondent’s Dinner.

Back then Colbert was a former Daily Show correspondent still trying to escape the gigantic shadow of his former boss. He’d begun his satirical spin-off only a year earlier and made a minor name for himself channeling Fox News blowhards (specifically “Papa Bear” Bill O’Reilly). It was years before his (first) run for President, before he testified to Congress, before he sponsored an Olympic speed skating team, before he shot his DNA into space, before he had a Ben and Jerry’s flavor named after him, and before he started Bill Clinton’s Twitter account. No one knew much about him.

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Colbert’s then-controversial roast of Bush, who sat grim-faced only a few feet away, showed that the newest Comedy Central host had balls of steel. The C-Span video of his withering, 16-minute podium speech, punctuated by muffled peals of laughter and enough awkward tension to make Dick Cheney’s heart explode, went instantly viral. It came at peak-period Dubya disdain, given the nation’s post-Katrina malaise and the increasingly unease about the war in Iraq,  and conveniently blew up the Colbert brand.

The speech proved to be as divisive as the term “Freedom Fries,” or – to make a 2006-specific reference – James Blunt’s “You’re Beautiful.”

The fallout from Colbert’s speech was predictable, but efficient: Liberals hailed it as brilliant and courageous, and conservatives decried it as a disrespectful attack on a sitting President. It all added up to enough juicy Colbert Report buzz to make the 2006-spawned Borat yell “Very nice!” for the umpteenth time. And it definitely spurred WHCD organizers to book the creakily bi-partisan, eighties-era impressionist Rich Little as the 2007 host.

Now, nearly a decade later, as we enter the waning days of Obama’s second term, earnestly progressive MSNBC is at least as much of a punchline as the indefatigable GOP drumbeaters at Fox News. And so the demise of the “Steven Colbert” character, ushered out tonight by his Grim Reaper pal “Grimmy”, already seems strangely overdue. It was an unforgettable, virtuoso performance, but ten years of spoofing cable news pundit jackassery is more than enough. Now it’s time to see if Colbert will have the same appeal as his alter-ego—and wait for when that guy invites O’Reilly over to chat.

Photos by Roger L. Wollenberg-POOL / Getty Images