By XAMXAM

NEW YORK — Few political figures have been as sensitive to mockery as Donald Trump, and few entertainers have been as persistent in provoking it as Jimmy Kimmel and Rosie O’Donnell.

Their latest appearances on late-night television, sharply critical and widely circulated online, reignited a dynamic that has spanned nearly two decades: a president who treats ridicule as a threat, and comedians who insist it is a form of accountability.

On recent broadcasts, Kimmel delivered monologues cataloging Trump’s public statements and reversals, while O’Donnell — long one of Trump’s most vocal celebrity critics — joined in with blunt, personal condemnation. The segments were comedic in structure, but political in intent, framing Trump not as an abstract figure of power but as a repeat subject of satire.

Trump’s response followed a familiar pattern. He denounced the criticism on social media, criticized networks by name, and suggested that entertainers who mock him are abusing their platforms. While such reactions are not new, the intensity of his engagement — particularly with O’Donnell — underscores how deeply he internalizes cultural ridicule.

A Feud That Predates Politics

The conflict between Trump and O’Donnell began well before Trump entered electoral politics. In 2006, while Trump was still best known as a real-estate developer and reality-television host, O’Donnell criticized his conduct during a Miss USA controversy on The View. Trump responded with public insults, legal threats, and repeated personal attacks.

The exchange became emblematic of Trump’s approach to criticism: counterpunch aggressively, personalize the conflict, and never retreat. O’Donnell, for her part, refused to disengage, continuing to frame Trump as a symbol of elite hypocrisy and media manipulation.

Kimmel entered the dynamic from a different angle. As host of a major network late-night show, he has repeatedly used humor to contextualize Trump’s statements, often juxtaposing past remarks with present claims. The technique is simple but effective: let the subject’s own words do the work.

Comedy as Political Pressure

What distinguishes Kimmel and O’Donnell from many other critics is not simply their opposition to Trump, but their insistence on repetition. The jokes recur. The themes return. The memory is long.

Political scientists note that satire functions differently from traditional criticism. It does not aim to persuade through argument, but to destabilize authority by making it familiar, fallible, and ridiculous. For leaders who rely heavily on projection of strength, ridicule can be uniquely corrosive.

Trump’s reaction suggests he understands this instinctively. He has praised entertainers who flatter him, condemned those who criticize him, and repeatedly questioned the legitimacy of media platforms that host dissent. The line between political grievance and cultural resentment is often thin.

The Limits of Control

Unlike legal disputes or legislative battles, cultural criticism cannot be easily neutralized. A joke cannot be subpoenaed. A monologue cannot be vetoed. The audience decides whether it lands.

That may explain why Trump’s responses often appear disproportionate. In the past, he has suggested changes to media regulations, attacked corporate owners of networks, and publicly celebrated the cancellation of critical voices. Each move reinforces the impression that mockery, more than policy disagreement, provokes his sharpest reactions.

For Kimmel and O’Donnell, the persistence of the feud has become part of the message. In interviews, both have argued that comedy has a civic role: to puncture power, to document patterns, and to refuse intimidation.

A Familiar Cycle, Renewed

The latest exchanges did not introduce new allegations or revelations. Instead, they replayed a cycle that audiences have seen many times before: ridicule, reaction, escalation.

What has changed is context. Trump is no longer merely a celebrity responding to criticism; he is a political figure whose relationship with the press and with dissent has tangible consequences. That reality gives late-night comedy a sharper edge, even when it relies on familiar punchlines.

Whether satire meaningfully constrains political power remains an open question. But as long as Trump continues to respond to jokes as if they were existential threats, comedians like Kimmel and O’Donnell are unlikely to stop telling them.

In the end, the exchange says as much about Trump as it does about his critics. For a leader who prides himself on dominance, laughter remains an opponent he has never quite learned to defeat.