David Letterman’s Late Show carved out a distinctive niche in late-night television during its run from 1993 to 2015, characterized by a sharp, cynical edge that gleefully punctured the bloated pretensions of entertainment culture and advertising. Letterman’s humor thrived on absurdity and irreverence, whether he was tossing watermelons off rooftops, mocking self-important celebrities, or skewering the inanity of corporate branding with segments like “Stupid Pet Tricks” or his sarcastic Top Ten lists. His approach exposed the artifice of showbiz and consumer culture, often making the audience complicit in the joke. While the show relied on advertising revenue, Letterman’s biting commentary maintained a distance from the system, offering a subversive critique that resonated with viewers skeptical of the polished veneer of mainstream media. This outsider stance made the Late Show a cultural touchstone for those who saw through the glitz of Hollywood and Madison Avenue.

When Stephen Colbert took over the Late Show in 2015, the tone shifted dramatically, reflecting a broader transformation in late-night television and its relationship to power. Colbert, fresh from his satirical Colbert Report persona, initially promised a continuation of sharp wit but gradually aligned the show with establishment narratives. Where Letterman’s humor was anarchic and apolitical in a broad sense, Colbert’s Late Show became a platform for partisan talking points, often indistinguishable from the rhetoric of cable news. His monologues and interviews leaned heavily into progressive orthodoxy, embracing a moralizing tone that contrasted with Letterman’s detached irony. The show’s reliance on advertising persisted, but the critique of consumer culture was softened, replaced by a focus on signaling alignment with corporate and political elites. This shift mirrored a broader trend in media, where late-night shows moved from cultural commentary to vehicles for approved messaging, often prioritizing ideology over humor.

The most striking evolution was the Late Show’s descent into what critics have called “Trump Derangement Syndrome,” a fixation on former President Donald Trump that dominated Colbert’s content during and after Trump’s presidency. Night after night, monologues devolved into repetitive anti-Trump tirades, often lacking the nuance or wit of Letterman’s broader cultural jabs. This obsession alienated viewers who craved the clever, universal absurdity of the Letterman era, replacing it with divisive, one-note political preaching. While Letterman ridiculed all sides of the establishment with equal glee, Colbert’s show seemed to cozy up to power structures—whether corporate sponsors or political figures—provided they aligned with its worldview. The result was a Late Show that felt less like a subversive comedy haven and more like a mouthpiece for a specific ideological camp, reflecting a cultural shift from questioning authority to enthusiastically polishing its boots.