Stephen Colbert’s ‘Truthiness’ Turns 20: Why His Satire Still Hits Hard
Two decades after The Colbert Report changed political comedy, Stephen Colbert faces an uncertain future but his impact on American satire is undeniable.
New York, October 17 EST: Twenty years ago tonight, a man in a navy suit sat at a desk beneath a bald eagle logo and told America that “truthiness” mattered more than truth. His name was Stephen Colbert, and his fake news show, The Colbert Report, would go on to redefine political comedy.
Now, two decades later, Colbert’s creation is being celebrated again. People magazine marked the anniversary this week with a warm, fan-minded tribute a look back at five of the show’s best moments, from the legendary 2006 White House Correspondents’ Dinner roast to Colbert’s mock presidential run that briefly made punditry feel like performance art.
The Birth of a Persona
When The Colbert Report premiered on Comedy Central in October 2005, nobody knew quite what to make of it. It looked like a right-wing talk show, sounded like one, and yet… didn’t. Colbert’s pompous, chest-thumping alter ego modeled after the blowhard cable anchors of the time was so committed to the bit that viewers sometimes forgot it was satire.
But that was the magic. He wasn’t playing a character to make fun of politicians. He was parodying the performance of certainty itself. “Truthiness,” as he called it, was the gut feeling that replaced facts. The word landed in the Merriam-Webster Dictionary the following year, and the Colbert Nation was born.
People’s anniversary feature revisits moments like that the verbal jousts with guests, the biting “Better Know a District” interviews, and of course, that brutal Correspondents’ Dinner monologue that left President George W. Bush frozen in his seat. Watching them now, they feel oddly fresh, even prophetic.
Colbert’s Shadow Over Late Night
Since The Colbert Report ended in 2014, the landscape it helped shape has shifted dramatically. Colbert moved to CBS and inherited The Late Show from David Letterman, bringing with him the moral weight and occasional melancholy of a man who once spent nine years pretending to be someone else.
That makes this anniversary bittersweet. In July, CBS confirmed that The Late Show with Stephen Colbert will end its run in May 2026, part of what the network called “a financial restructuring.” It’s a bloodless explanation for a decision that, to fans, feels anything but.
According to AP News, insiders believe Colbert’s politics especially his cutting commentary on Donald Trump and his parent company’s corporate deals made him a target. The news sparked an immediate backlash. A “Save Colbert” protest broke out outside the CBS Broadcast Center in Manhattan in July, and The Guardian reported that more than 250,000 fans signed a petition urging the network to reverse course.
Bette Midler and a Farewell in Slow Motion
Earlier this week, the emotion behind that support was on full display. On October 14, Bette Midler appeared on The Late Show and serenaded Colbert with a tongue-in-cheek version of her classic “Wind Beneath My Wings”, rewritten to include Lord of the Rings jokes and a few jabs at Trump.
Entertainment Weekly described it as both hilarious and tender the kind of segment Colbert has always done best. When Midler finished, Colbert looked genuinely choked up. “I don’t know whether to retire or start a band,” he joked, his voice cracking just a little.
It was a moment that felt less like a skit and more like a goodbye not just to a show, but to an era of late-night that still cared about ideas.
Still Stirring Trouble
Despite the looming end, Colbert hasn’t softened. Just this week, he used his monologue to rip into a TIME magazine cover featuring Trump, unveiling a set of “alternative” versions that placed the former president in increasingly absurd company. One mock-up, as The Daily Beast noted, even paired Trump with Jeffrey Epstein a joke that nearly sent CBS’s censors scrambling.
For Colbert, that kind of provocation isn’t rebellion so much as muscle memory. It’s what he’s always done: point at power, laugh at it, and let the audience decide what the joke means.
The Long Echo of ‘Truthiness’
Rewatching those old Colbert Report clips today the confident smirk, the flag pin, the absurd moral certainty you realize how much he changed the way Americans think about media. Before Colbert, political satire usually looked sideways at power. He looked it straight in the eye.
He created a fake pundit who, by sheer conviction, revealed more about the truth than the real pundits ever did. And in doing so, he made audiences smarter or at least a little more suspicious of certainty.
In a 2007 interview, Colbert said something that still sums up his work: “I’m not cynical. I’m hopeful. Because hope is the only reason to laugh.”
Two decades on, that hope still hums beneath everything he does, even as the corporate clock winds down on his CBS tenure. Whether he finds a new platform or steps back entirely, Colbert’s voice the human one, not the character has already carved its place in American satire.
For fans who tuned in every night to hear him make sense of the nonsense, that’s reason enough to celebrate.
New Jersey Times Is Your Source: The Latest In Politics, Entertainment, Business, Breaking News, And Other News. Please Follow Us On Facebook, Instagram, And Twitter To Receive Instantaneous Updates. Also Do Checkout Our Telegram Channel @Njtdotcom For Latest Updates.
Trained in war zones, raised in Newark, and seasoned in city hall, Jordan blends grit reporting with deep integrity. From floods to finance bills, they’re always first on scene and last to leave.
