New York — Over more than a decade, two very different figures — a former president and a late-night television host — have repeatedly demonstrated how humor, when paired with timing and documented facts, can unsettle even the most media-savvy political figure. The latest example arrived this year when Jimmy Kimmel, hosting the Academy Awards, read aloud a social-media post attacking him by Donald Trump, then calmly thanked the former president on live television. The reaction that followed — online outrage, all-caps rebuttals and renewed media fixation — felt familiar.

It was familiar because the playbook was written years earlier by Barack Obama.

In 2011, at the White House Correspondents’ Dinner, Mr. Obama addressed the then-private citizen seated only a few feet away, dismantling Mr. Trump’s promotion of the “birther” conspiracy with a sequence of deadpan jokes and documentary evidence. The routine was restrained, almost clinical. The laughter in the room came not from exaggeration but from recognition. The camera cuts — lingering on Mr. Trump’s unsmiling face — became part of political folklore.

That night is now widely regarded as a hinge moment in modern political television: a demonstration that mockery grounded in the public record can carry more force than direct confrontation. Mr. Obama never raised his voice. He simply let the facts, and the room’s reaction, do the work.

More than a decade later, Mr. Kimmel has adapted that same principle for a media environment shaped by social feeds and instant replay. At the Oscars in March 2024, he read Mr. Trump’s criticism of the ceremony verbatim, treating it as audience participation rather than provocation. The punchline arrived not through insult but through timing. The crowd laughed, the clip went viral, and the former president responded exactly as he had in earlier episodes: publicly, angrily and at length.

Media analysts note that the effectiveness of these moments lies in their restraint. “Neither Obama nor Kimmel invents a caricature,” said one television historian. “They simply present Trump’s own words or actions and allow the audience to connect the dots.”

The pattern has repeated across years and formats. In 2016, during his final Correspondents’ Dinner, Mr. Obama again took aim — briefly, precisely — before ending his remarks with a famously understated sign-off. The moment was interpreted by many viewers as a closing argument delivered in the language of comedy. Mr. Trump, by then a presidential candidate, again appeared unmoved in the room, though allies later described lingering resentment.

Mr. Kimmel’s approach has been more improvisational but no less disciplined. He often frames his monologues as reactions rather than attacks, positioning himself as a reader of the news rather than a partisan actor. That posture became especially visible during a brief suspension of his show in 2025, after a controversial monologue prompted corporate unease. When the program returned, Mr. Kimmel framed the episode as a test of free expression, not a personal grievance — a move that drew support from fellow hosts and renewed attention from critics.

What unites these episodes is not simply humor, but a shared understanding of audience psychology. Viewers recognize authenticity. When the jokes align closely with verifiable events — a conspiracy theory promoted on television, a social-media post written in haste — the satire gains weight. The laughter carries an implicit judgment.

Mr. Trump’s responses, by contrast, have tended to amplify the original moment. His rebuttals often revive the very clips he objects to, extending their lifespan and reach. In that sense, the cycle is self-perpetuating: satire provokes reaction, reaction becomes content, and the loop closes.

For supporters of late-night comedy, the episodes underscore its enduring civic role. Comedy, they argue, remains one of the few spaces where power can be challenged without formal opposition. For critics, the same moments exemplify media excess and political polarization.

Either way, the historical throughline is difficult to ignore. From a ballroom in Washington to a global broadcast watched by millions, the same lesson has played out repeatedly: timing matters, facts matter, and volume alone rarely wins the moment.

As one longtime observer of political television put it, “When comedy doesn’t have to stretch the truth, it hits harder.”