In a revealing impromptu interview at The Atlantic Festival on September 18, 2025, former late-night legend David Letterman and The Atlantic’s editor-in-chief Jeffrey Goldberg discussed the suspension of Jimmy Kimmel’s show following controversial remarks about Charlie Kirk’s assassination. The conversation illuminated a longstanding undercurrent of antipathy toward conservative policies among late-night comedians, a tradition Letterman himself navigated with subtlety during his 30-year tenure. While Letterman often cloaked his political jabs in humor, targeting six presidents from Carter to Obama with a measured approach, today’s hosts like Stephen Colbert and Jimmy Kimmel have increasingly shed this veneer, openly displaying their disdain for conservative figures. Letterman’s critique of ABC’s “ridiculous” suspension of Kimmel’s show and his warning against “managed media” suggest that he sees this overt bias as a dangerous departure from the more restrained, if still slanted, commentary of his era.

This shift in late-night comedy’s tone coincides with Donald Trump’s unprecedented dominance in shaping public discourse, a phenomenon that has evidently rattled the traditional gatekeepers of cultural influence. Trump, with his knack for sharp, memeable content and direct engagement on platforms like Truth Social, has outmaneuvered comedians in the influence game, commanding the national mood with a blend of humor and provocation that resonates widely. Unlike Letterman, who maintained a veneer of neutrality to appeal broadly, Colbert and Kimmel have leaned into their progressive biases, alienating conservative audiences while struggling to match Trump’s raw charisma and viral appeal. Their reactions to events like Kirk’s assassination—Kimmel’s inflammatory comments and Colbert’s taunts—reveal a frustration born of being outshone by Trump’s ability to dictate narratives, as seen in his swift condemnation of Kimmel’s remarks and his framing of the left as complicit in political violence. This dynamic has pushed comedians to expose their ideological cards, abandoning the subtlety Letterman mastered.

The contrast between Letterman’s era and the current landscape underscores a broader cultural shift where Trump’s outsized presence has redefined political entertainment. Letterman, in his interview with Goldberg, lamented the “misery” of today’s polarized media, hinting that comedians’ overt hostility risks further eroding free speech—a concern he never faced to the same degree during his career. While Letterman’s jabs at conservatives were often veiled in irony, allowing him to maintain plausible deniability, Colbert and Kimmel’s explicit attacks, especially post-Kirk, have fueled perceptions of bias so blatant that even liberal outlets like CNN noted the backlash. Trump’s ability to craft funnier, more shareable content—often at the expense of his detractors—has not only diminished the cultural clout of late-night hosts but also exposed their rage against conservative policies as a desperate bid to reclaim relevance in a media landscape he dominates.