The phrase refers to the appearances of the former President of the United States, Donald Trump, on The Tonight Show Starring Jimmy Fallon. These appearances, particularly one in September 2016, involved interviews and comedic segments hosted by Jimmy Fallon. A notable instance included Fallon playfully messing up Trump’s hair during a lighthearted exchange.
These interactions garnered significant attention due to the intersection of politics and entertainment. They provided a platform for the then-candidate to connect with a broader audience, showcasing a less formal and more approachable persona. However, the lighthearted nature of the interview also drew criticism, with some arguing that it normalized or downplayed the seriousness of the political landscape during a crucial election year. This prompted debate regarding the role of late-night television in political discourse and candidate portrayal.