The uneasy relationship between political power and popular entertainment resurfaced this week after former President Donald Trump traded public criticism with the late-night host Jimmy Kimmel and the actor and artist Jim Carrey, renewing a debate over satire, free expression and the boundaries of political speech.

The latest flare-up followed Mr. Trump’s deletion of a social media post that drew bipartisan criticism for sharing an image widely described by lawmakers as offensive and racially insensitive. Supporters characterized the post as internet humor; critics, including some members of Mr. Trump’s own party, called it inappropriate and urged an apology. The White House did not issue a formal retraction beyond removing the image.

The controversy gained new momentum when Mr. Kimmel referenced Mr. Carrey’s political artwork during a recent monologue. Since 2017, Mr. Carrey has used paintings and illustrations to portray Mr. Trump in stark, often unflattering terms — as authoritarian, corrupt or consumed by ego. The images, shared on social media, have functioned as a sustained visual critique rather than a single punchline.

Mr. Kimmel framed his remarks around the role of artists in a democracy. Satire and protest art, he argued, are longstanding tools for challenging authority. Mr. Trump responded on social media and in interviews by criticizing entertainers broadly, questioning their talent and television ratings, and suggesting they were motivated by personal animus rather than principle.

The exchange reflects a pattern that has defined much of Mr. Trump’s public life. From his first presidential campaign through his time in office and beyond, he has sparred frequently with comedians, actors and television hosts who use their platforms to lampoon his rhetoric and policies. In turn, Mr. Trump has portrayed such criticism as evidence of media bias and cultural elitism.

Mr. Carrey’s involvement traces back several years. In September 2018, he appeared on “Jimmy Kimmel Live” to explain why he had begun producing overtly political artwork. He described drawing authority figures as a child and said he felt compelled to use painting as a form of civic expression. His portraits of Mr. Trump were deliberately confrontational, invoking imagery of corruption and threats to democratic norms.

“Artists have a responsibility to defend innocence,” Mr. Carrey said at the time, arguing that entertainers should not serve merely as distractions. He criticized what he described as secrecy and misinformation within the administration and mocked proposals, including a suggestion that citizenship could be revoked from critics — a step legal scholars have said a president cannot unilaterally take.

Over time, Mr. Carrey’s feed became a steady stream of political commentary rendered in paint. Some works depicted Mr. Trump sinking into a swamp; others cast him as a monstrous figure symbolizing excess or division. Admirers praised the boldness; detractors dismissed the art as partisan caricature.

Mr. Kimmel, meanwhile, has positioned his program as a forum for pointed political humor. After his show was briefly suspended during a contract dispute, he returned with a monologue warning that attempts to intimidate comedians could chill free expression. “A leader who punishes jokes threatens democracy,” he said, arguing that public officials must tolerate criticism as part of the office.

Mr. Trump has rejected that framing, asserting that he is the target of unfair and relentless attacks from entertainment figures. On his social media platform, he has labeled certain hosts “untalented” and accused networks of bias. In response, Mr. Kimmel has suggested that such rhetoric reflects discomfort with scrutiny rather than substantive disagreement.

The dispute highlights how political conflict increasingly unfolds across multiple cultural arenas: television studios, social media feeds, gallery spaces and awards ceremonies. At a recent event, Mr. Kimmel thanked Mr. Trump with heavy irony for providing “endless material,” a remark that drew laughter but also underscored the degree to which political satire now forms a steady backdrop to national life.

The broader question is whether such exchanges clarify or intensify division. Supporters of Mr. Kimmel and Mr. Carrey argue that satire exposes hypocrisy and holds leaders accountable in ways that traditional reporting cannot. Critics counter that highly stylized ridicule can deepen polarization and reduce complex policy debates to personal animus.

Lawmakers who condemned Mr. Trump’s deleted image said public figures bear special responsibility in their speech. Yet few called for formal sanctions, reflecting the tension between disapproval and constitutional protections for expression.

Historians note that satire has long occupied a contentious but vital place in American democracy. From political cartoons of the 19th century to television parodies during the Vietnam War and Watergate, artists have challenged presidents with exaggeration and irreverence. What distinguishes the present moment is the speed and reach of digital platforms, where a painting or a monologue can circulate globally within minutes.

For Mr. Trump, whose political identity has been shaped in part by his mastery of media spectacle, the confrontations with entertainers serve both as irritants and as opportunities to rally supporters against perceived cultural elites. For Mr. Kimmel and Mr. Carrey, the clashes reinforce their argument that creative expression is not merely entertainment but civic engagement.

As the country approaches another contentious election cycle, the intersection of politics and performance shows little sign of retreat. In a media environment where art, humor and governance intersect daily, the struggle over who controls the narrative — and how far satire should go — remains an enduring feature of the national conversation.