Wit & Attitude Quote by Conan O'Brien

Conan O'Brien's joke works because it treats a deadly serious media event like a playground for status anxiety. The setup is pure cable-news gravitas: Dan Rather, the embodiment of mid-century broadcast authority, sits down with Saddam Hussein, a figure who had become a shorthand in American culture for opaque evil and geopolitical menace. Then O'Brien performs the classic late-night reversal: the insulting question aimed at Saddam ("what it was like to talk to a crazy man") gets boomeranged back onto the interviewer. Saddam's line, "It's not so bad", turns the dictator into the snarky talk-show guest and demotes Rather to the punchline.

The intent isn't to humanize Saddam so much as to puncture American media self-importance. The subtext is that TV journalism, with its solemn tone and self-mythology, can start to look absurd when placed next to real power and real violence. By letting Saddam deliver the insult, O'Brien also exposes how interview formats smuggle in arrogance: the assumption that the American anchor is the sane, neutral center and everyone else is an object to be diagnosed.

Context matters: this is late-night comedy in an era when national news anchors still carried a priestly aura, and when Saddam was a looming headline villain. O'Brien isn't weighing policy; he's mocking the cultural theater around it, where even a dictator can be made into a vehicle for a one-liner about who gets to define "crazy" on television.