O’Brien and his guest touched on their shared experience of coming up in the entertainment industry during the early 90s. Despite their different paths, they both recognized the challenges of breaking into the industry. O’Brien humorously remarked how ancient the 90s now sound to younger generations.

The conversation took an interesting turn when the topic of test shows came up. O’Brien asked if his guest had been on a test show, to which they responded negatively. This led to a discussion about the dysfunction and insanity of those early shows and the interesting mix of celebrities who appeared on them. O’Brien recalled a memorable encounter with Mickey Rooney hanging from a garment rack, blaming his hair loss on Harry Warner in 1941.

As the conversation continued, O’Brien reflected on the early days of his show and how it felt like it took forever to gain acceptance and reach a point of success. He spoke about the feeling of being an “elder statesman” now and how time has flown by.

The guest chimed in, sharing their own perspective on success and failure, having faced setbacks and cancellations in their career. They discussed their different expectations and how their journey led them to a different understanding of what it means to “make it” in the entertainment industry.

Throughout the conversation, both O’Brien and his guest shared humorous anecdotes and reflections on their experiences in the industry. The talk show segment provided an entertaining and lively insight into the ups and downs of creating a successful TV show.

Overall, this episode of “Conan O’Brien Needs A Friend” showcased not only the wit and humor of the talk show host but also provided an intriguing glimpse into the life of a comedian navigating the ever-evolving entertainment world.