Late Night Roundup highlighted a sharp rebuke of President Trump's Pearl Harbor comment during his press conference with Japanese Prime Minister Sanae Takaichi. Host Jimmy Kimmel quipped, 'There is no doubt in my mind that everything he knows about Pearl Harbor begins and ends with a movie starring Ben Affleck.' Kimmel's jab underscored the awkwardness of Trump's question to Takaichi about surprise attacks, comparing it to Japan's knowledge of Pearl Harbor. This incident, along with Trump's praise of Takaichi's English and his own admission of not learning Japanese, became a focal point of late-night comedy, drawing criticism for its historical insensitivity and potential diplomatic awkwardness.

The segment reflects a recurring theme of Trump's verbal missteps drawing significant media and comedic scrutiny.