In September 2015, Donald Trump made his debut on CBS’s “The Late Show With Stephen Colbert”. At that time, the show was still navigating its new host. Initially, Trump apologized to Colbert, setting a tone for their unlikely partnership.
As late-night TV began to shift due to streaming services, comedians’ influence waned. Meanwhile, Trump’s appearances gained more power. This marked an interesting convergence of politics and entertainment in late-night television.
Source: https://www.washingtonpost.com/entertainment/2025/07/19/trump-colbert-cancel-late-night