Remembering Why Stephen Colbert Is An Absolute Legend in Political Comedy

Medium close-up portrait of a smiling Stephen Colbert wearing his signature wire-rimmed glasses, a black suit, and a patterned tie against a blue background.

The other day, The Late Show on CBS came to an end with the final episode of Stephen Colbert’s run as host. While late-night shows are proving to be unprofitable in the age of on-demand streaming and the near collapse of traditional cable, it feels like a good moment to reminisce about how influential Stephen Colbert has been in political comedy and commentary.

Television hosts Stephen Colbert and Jon Stewart sitting across from each other at a wooden anchor desk, looking down seriously during an early episode of The Daily Show on Comedy Central.

Almost everybody remembers him first as one of the co-anchors of The Daily Show during its prime, alongside a newly graying Jon Stewart. He was so funny on the show that he simply could not be contained within Comedy Central’s flagship political program.

A low-resolution screenshot of Stephen Colbert appearing as a guest on a Fox News program with Bill O'Reilly, sitting across a glass desk from the host with a television screen displaying "The Daily Show" in the background.

So for years, he went on to create The Colbert Report, which brilliantly cast him as a fictional version of himself: a hardline conservative in the mold of Bill O’Reilly, often parodying the Fox News host in inspired fashion. What made The Colbert Report so satisfying was that everyone knew he was pretending. And much to Bill O’Reilly’s frustration, Stephen Colbert almost never broke character during its entire run.

Comedian Stephen Colbert wearing a tuxedo and black bow tie, speaking dynamically and gesturing with one hand at a podium featuring the seal of the President of the United States at the White House Correspondents Dinner.

Arguably his greatest achievement was serving as the featured comedian at the White House Correspondents’ Dinner during the George W. Bush administration. The dinner is usually a pretty funny event, but Bush was not among those who found it funny that night. Conservatives were furious, while liberals found it absolutely hilarious.

Stephen Colbert in a blue suit and matching tie standing on the stage of The Late Show, with a large window backdrop showing a lit-up New York City skyline at night.

Then, over a decade ago, following David Letterman’s retirement, CBS gave The Late Show to Colbert, much to the anger of many conservatives and Craig Ferguson fans. Technically, it was not even a change of employer, since Comedy Central and CBS are both owned by the same parent company. But he could no longer maintain the same persona, and we got to see the real Stephen Colbert for the first time. I will admit I was not the biggest fan of The Late Show because it was not as funny as The Daily Show or The Colbert Report, but Stephen Colbert never lost his values or focus. I had tremendous respect for him when he had Ted Cruz on as a guest. The crowd booed, and he asked his audience not to treat his guest that way, noting that there is a certain ethic that comes with inviting someone onto your show in the first place. Like him or not, if you truly know Stephen Colbert, you know he is a man of integrity.

A blurry AI video of Stephen Colbert being comically lifted up and tossed into a large green dumpster by Donald Trump during a late-night comedy sketch on the Late Show on CBS.

Unfortunately, Donald Trump and the CEO of Paramount-Skydance are reportedly on good buddy-buddy terms, and while it was never officially confirmed, it became widely speculated that Trump heavily pressured the network regarding Colbert’s future. Conveniently for Trump, the show also carried a high production cost with almost no profitability. But honestly, I wish Stephen Colbert would sue Donald Trump over this, because it would be a clear First Amendment issue and a transparent attempt to silence a critic. Just the other day, Trump posted an AI-generated video depicting himself throwing Colbert into a trash can. It is shameful that a president (who should be focused on improving a deeply unhappy country) spends so much time lashing out at critics and perceived enemies.

Stephen Colbert in a dark suit standing and clapping on a late-night television set next to guest Michelle Obama, who is sitting at a round wooden desk and smiling.

Now his political comedy career appears to be on pause. The only project he is currently working on is a Lord of the Rings production with Peter Jackson, which is a passion project of his. If that is all he does next, I wish him the best of luck and congratulate him on a remarkable career. You would think he would be a natural choice to become the next permanent host of The Daily Show, but that is also a Paramount platform. I would personally love to see him replace Bill Maher in the Real Time slot, but with Paramount likely merging with Warner Bros., the same problem could arise there too. The most realistic path forward is probably a podcast, which could actually be pretty interesting, especially if it offered a genuine alternative to the kind of content you get on garbage Reich Wing podcasts like The Joe Rogan Experience.

One Comment Add yours

  1. Unknown's avatar Anonymous says:

    It burns my biscuits how some of the networks are letting trump dictate to them and to what we watch. And you are correct, he is a legend in political comedy.
    Sandra

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