"This article is part of The Poynter 50, a series reflecting on 50 moments and people that shaped journalism over the past half-century - and continue to influence its future. As Poynter celebrates its 50th anniversary, we examine how the media landscape has evolved and what it means for the next era of news. In a wide-ranging interview, Howard Stern asked Conan O'Brien about everything from his time as a writer for "Saturday Night Live" to the comedian's final days as host of "The Tonight Show.""
"Stern brushed off the idea that credentials mattered. "It's being funny," Stern said. "And it's a bitch." O'Brien said he'd struggled with self-doubt and had felt depressed. It was an opening for the self-described "King of All Media." "Do you suffer from depression?" Stern asked his famous guest outright. "Are you medicated?" "I'm medicated," O'Brien confirmed. "You are?" Stern asked. "Yeah," O'Brien said. "I used to think I needed to be incredibly unhappy to be funny ... and people tell you that's not true," O'Brien said. "You get to a point where you don't care if it's true or not. You really don't. You just think, 'You know what? I'd rather be happy.'""
Howard Stern conducted a wide-ranging interview with Conan O'Brien that covered O'Brien's SNL writing days and final nights on The Tonight Show. Stern emphasized that credentials matter less than being funny and used direct questioning to elicit candid responses. Conan O'Brien disclosed struggles with self-doubt and depression and confirmed that he is medicated. O'Brien described a shift from believing unhappiness was tied to comedy toward preferring happiness. Stern's style evolved from provocative to more mature and reflective, and he helped popularize long-form interviews across broadcast radio and subscription audio platforms.
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