David Letterman and Conan O’Brien give a comedy history lesson

Late night legend David Letterman was the first guest on season two of Conan O’Brien Needs a Friend.

Conan O’Brien set the bar pretty high for season two of his podcast in just the first episode. David Letterman is featured in the latest “Conan O’Brien Needs a Friend” as the two late night legends talked about all things comedy.

When season two was announced, upcoming guests like Paul Rudd, Ellen Degeneres, and Tina Fey got fans excited for another incredible run of podcasts from Team Coco. David Letterman’s name stood out above the rest given his icon status and influence on O’Brien.

The careers of Letterman and O’Brien have a number of connections. O’Brien applied for a writer’s job on Letterman’s show. It was O’Brien who graduated from Saturday Night Live writer to Letterman’s successor as host of Late Night on NBC. And Letterman was a supportive voice behind O’Brien during the Tonight Show debacle with Jay Leno.

But fans know that O’Brien and Letterman aren’t the type to reflect too heavily own their own careers and accomplishments. Both deflect praise in favor of turning the spotlight on to someone else. That was the case for most of the podcast as the two celebrated comedy heroes between touching on life for a late night host.

The episode gives us insight into Letterman’s decision to retire from The Late Show, revealing that he wish he had done so earlier. We also hear about the challenge of finding enjoyment in doing a late night show night after night, year after year. It is a similar topic that Conan O’Brien discussed with Jimmy Kimmel last season.

Letterman didn’t let O’Brien celebrate him too much or talk about the success of The Late Show. Instead the two lauded the careers of comedians like Johnny Carson, Bob Hope, Rich Hall, Steve Martin, Martin Short, Tina Fey, and Norm MacDonald. The two give listeners a sense of who and what they appreciate when it comes to comedy. It’s a history lesson and some homework for any comedy fans who want to learn more about what makes O’Brien and Letterman laugh.

The podcast wraps up with an update on the horse story that O’Brien told on The Late Show with Stephen Colbert. The “beautiful misunderstanding” was a horse that Letterman sent to O’Brien with the intent of getting it on Conan.

The first episode of season two of “Conan O’Brien Needs a Friend” will definitely be in the conversation for the best of the season. If it’s any indication, the podcast will only get better from here.