Conversations with Bert is a two-part video posted to the Sesame Street YouTube Channel on May 18 and 20, 2011. Bert hosts a talk program from his round table, conversing with guest Andy Samberg.
In the first part, they talk about socks throughout history (including Puttees) and rocket packs. The last book Bert read was one of those depressed Russian writers, and Andy's was Harry Potter; Bert feels Potter isn't developed enough as a writer. The intermission is signaled by Milk Break Time. (YouTube)
In the second part, Bert and Andy talk about their sock world views and Andy's favorite dry white toast joke. The video ends with Bert's Brain Busters (a game where Bert asks Andy a series of questions that he has to answer as fast and as honestly as he can) and Andy's comedy banter. (YouTube)
David Rudman directed the video[1] and provides the opening voiceover.