Howard Stern and Conan O’Brien deliver another must-listen conversation

A sit down conversation between Howard Stern and Conan O’Brien has become an event you can’t miss.

Whether it is on radio, on late night television, or on a podcast, the need for “chemistry” between the host and guest is a common cliche. But it’s hard to find another way to describe the connection between Howard Stern and Conan O’Brien, two men who on the surface bring very different elements to the table.

In promoting his book Howard Stern Comes Again, the radio legend named his 2015 interview with O’Brien as his favorite from his long, storied career. It certainly is worth listening to if you find a full version online. The two cover everything from O’Brien’s late night career including the Tonight Show fiasco. But for Stern, what stood out was discovering more about O’Brien’s psychological makeup and use of therapy sessions.

That interview and much more was covered on this week’s episode of “Conan O’Brien Needs a Friend.” It was perhaps one of the best episodes yet of O’Brien’s podcast. Similar to conversations with Stephen Colbert and Dax Shepard, O’Brien and Stern struck a tone that was more insightful than funny but no less entertaining.

There probably is a fair amount of crossover between Conan O’Brien fans and Howard Stern fans. Yet even if you come to the podcast as only familiar with one over the other, you can appreciate the conversation. Fans of both are sure to finish the podcast having a better understanding of where O’Brien and Stern have been and where they want to be.

Stern highlights the special connection, or “chemistry,” that he felt with O’Brien. Much of that stems from their similar views on mental health and the struggles they have with accepting their fame as well as how their creative output is perceived.

The conversation is also motivational at times as well as emotional. Stern especially wanted to make the point that nothing was handed to him and that his personal wealth doesn’t protect him from insecurities or bouts of self-doubt.

It’s easy to see why O’Brien calls Stern the best interviewer in all of media. Not long into the start of the podcast does it feel like Stern is interviewing O’Brien. But that model of a back-and-forth is what makes their conversation so engaging. The listener feels like the third person in the room, participating in the conversation rather than listening to a prototypical podcast interview.

Other topics covered include Conan O’Brien’s discomfort with the Harvard “stigma,” how Howard Stern reacted live on radio during 9/11, and the value of having control over a creative legacy. All in all it is a must listen and well worth the time for fans of O’Brien and Stern alike.

“Conan O’Brien Needs a Friend” still has a handful of episodes left before it ends its first season. It will be challenging for anything to top the conversation between Conan O’Brien and Howard Stern. The good news is that doesn’t mean fans won’t still be getting quality episodes of one of the best podcasts going right now. And we certainly haven’t heard the last conversation between these two legends.