Jimmy Kimmel and Stephen Colbert ROASTS Trump On Live, Trump LOSES It.

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Late-Night Comedy’s Sharpest Shots: Jimmy Kimmel and Stephen Colbert Take on Donald Trump

In a series of high-profile moments throughout 2024 and 2025, late-night hosts Jimmy Kimmel and Stephen Colbert have emerged as leading voices in satirizing former President Donald Trump, turning his own words and actions into powerful comedic critiques.

The saga began at the 96th Academy Awards in March 2024, when Jimmy Kimmel boldly read Trump’s Truth Social rant live on stage. Trump had attacked Kimmel as the “worst Oscars host ever,” prompting Kimmel to hold up his phone and deliver the message verbatim to an audience that erupted with laughter. This moment not only went viral but also marked a turning point where comedy exposed Trump’s obsession with public image and thin skin.

Kimmel continued to mock Trump’s frequent social media outbursts, including a recent post criticizing the NFL’s kickoff rule and complaining about a Time magazine cover photo. His sharp humor highlights the former president’s fixation on trivial matters while serious political issues unfold.

Meanwhile, Stephen Colbert has delivered some of the most memorable late-night monologues targeting Trump. In 2017, Colbert famously called Trump’s brain “filled with cotton candy fantasies” during a scathing critique of the White House ballroom project. Later, after Trump’s guilty verdict in a hush money case in June 2024, Colbert led a live studio chant of “Lock him up,” echoing Trump’s own campaign slogan but turned back on him with biting irony.

Colbert’s 2023 monologue also included a pointed jab calling Trump “Vladimir Putin’s holster,” a line that sparked thousands of FCC complaints but ultimately reinforced the power of satire to challenge political figures.

Together, Kimmel and Colbert have used timing, wit, and national platforms to hold Trump accountable in ways traditional news media and legal systems have struggled to do. Their ability to weaponize Trump’s own words and slogans has made them central figures in the cultural conversation around power, accountability, and free speech.

Despite criticism from some political figures, including Senator Ted Cruz’s threats to cancel ABC’s license over Kimmel’s jokes, the comedians’ influence remains strong. Their ratings spike each time Trump attacks them, proving that humor continues to be a potent tool in American political discourse.

As Trump continues to dominate headlines with controversial actions and statements, Kimmel and Colbert’s ongoing comedic engagement serves as a reminder that sometimes, laughter is the sharpest form of truth.