On July 21, 2025, Stephen Colbert returned to The Late Show with a monologue that was equal parts comedic brilliance and fearless defiance. Addressing a viral rumor about former President Donald Trump wearing his pants backward during a speech, Colbert quipped, “Stephen Colbert Puts His Pants Back On For The Late Show,” using the absurd to segue into biting critiques of Trump’s ties to Jeffrey Epstein and CBS’s decision to cancel his show in May 2026. The segment, emblematic of Colbert’s razor-sharp satire, underscored a tumultuous moment for late-night television, as the cancellation sparked widespread speculation about political motivations tied to CBS’s parent company, Paramount, and its controversial dealings with Trump.
The announcement on July 17, 2025, that The Late Show with Stephen Colbert would end after 33 years—first under David Letterman and then Colbert—shocked fans and industry insiders alike. CBS executives, including Paramount co-CEO George Cheeks, insisted the decision was “purely financial” due to the “challenging backdrop in late night,” citing reports of $40 million in annual losses. Yet, the timing raised eyebrows. Just days earlier, Paramount settled a $16 million lawsuit with Trump over a 60 Minutes interview with Kamala Harris, a move Colbert publicly called a “big fat bribe” to secure FCC approval for an $8.4 billion merger with Skydance. The settlement, coupled with Colbert’s outspoken criticism of Trump, led many to suspect the cancellation was a political capitulation rather than a budgetary necessity.
Colbert’s response was quintessentially audacious. In his first monologue post-cancellation, he declared, “They made one mistake: They left me alive!” The audience erupted in chants of “Stephen! Stephen!” as he launched into a week-long tirade against Trump and CBS. From mocking Trump’s Epstein connections with lines like “diamond pervert status” to questioning CBS’s financial rationale with, “I could see us losing $24 million, but where could Paramount have spent the other 16 … oh yeah,” Colbert was unrelenting. His viral retort to Trump’s gloating Truth Social post—“Would an untalented man be able to compose the following satirical witticism? Go f—k yourself”—became a rallying cry for supporters.
The backlash was swift and polarized. Late-night hosts like Jon Stewart and Jimmy Kimmel rallied behind Colbert, with Stewart lambasting CBS for “bending the knee” to Trump and Kimmel posting, “Love you, Stephen. F*** you and all your Sheldons, CBS.” Protesters gathered outside the Ed Sullivan Theater, chanting “Colbert stays! Trump must go!” Democratic lawmakers, including Elizabeth Warren and Adam Schiff, demanded transparency, with Warren noting the cancellation came “just three days” after Colbert’s bribe comment. Conversely, conservative voices like Megyn Kelly criticized Colbert, urging him to “put on your big boy pants” and accept the cancellation “like a man,” referencing her own $30 million payout from NBC in 2019.
The cancellation reflects broader challenges in late-night television. With declining ad revenues and a shift toward digital platforms, shows like The Late Late Show and After Midnight have also ended. Yet, The Late Show’s consistent ratings dominance—2.4 million nightly viewers—made its demise particularly jarring. Insiders reported a “devastated” crew, describing the show as a “close-knit” family facing a tough job market. Speculation about Paramount’s merger with Skydance, led by pro-Trump billionaires Larry and David Ellison, intensified fears that other critical voices, like Stewart’s The Daily Show, could be next.
Colbert’s defiance positions him as a cultural lightning rod. By doubling down on Trump critiques, he’s daring CBS to act prematurely, potentially proving political motivations. If CBS pulls him early, he gains evidence of censorship; if they let him continue, he has a platform to speak freely for 10 months. This high-stakes gamble underscores late-night comedy’s role as a bastion of free speech in a polarized era. As Stewart noted, these shows contribute significantly to their networks’ value, yet face increasing pressure to conform.
The “pants” segment, while humorous, was a microcosm of Colbert’s strategy: using satire to confront power. Whether his stand is seen as brave or reckless, it highlights the precarious state of late-night TV and the broader media landscape. As The Late Show approaches its final bow, Colbert’s legacy as a fearless satirist is secure, but the questions surrounding his exit—financial, political, or both—will linger, shaping the future of comedy and free expression.
