Ep 21. Comedian and Crashing Star Pete Holmes on the Art of Stand-Up, Understanding Privilege and Conan

Comedian and Crashing Star Pete Holmes sits down with Carlos Watson for an engaging conversation about the art of stand-up comedy, understanding privilege, and his experience working with late-night talk show host Conan O'Brien.

The episode begins with Carlos asking Pete how he first got into stand-up comedy. Pete shares that he was always a class clown and loved making his friends laugh, but he didn't start performing stand-up until he was in his mid-20s. He talks about his first time on stage and how he bombed, but he was hooked and knew he wanted to keep pursuing comedy.

The conversation then shifts to the topic of privilege, and Carlos asks Pete about his experiences growing up and how they have shaped his worldview. Pete shares that he grew up middle-class and white in a predominantly black and Hispanic neighborhood in Boston. He acknowledges that he had certain advantages growing up that his peers did not have, and he is constantly learning how to use his privilege to help others.

Next, Carlos asks Pete about his experience working on Conan, where he was a writer and occasional performer for several years. Pete shares that working for Conan was a dream come true, and he learned so much about the industry and the art of comedy. He talks about the collaborative nature of the show and how everyone worked together to create the best possible content.

The conversation then turns back to stand-up comedy, and Carlos and Pete talk about the process of writing and performing jokes. Pete shares that he writes down everything that makes him laugh and then goes back to see if any of it can be turned into a joke. He also talks about the importance of being vulnerable on stage and sharing personal experiences with the audience.

As the episode comes to a close, Carlos and Pete talk about the future of comedy and how the industry is constantly evolving. Pete shares that he is excited to see more diverse voices and perspectives in comedy, and he encourages aspiring comedians to keep writing and performing even if it feels difficult or scary.

Overall, this episode of The Carlos Watson Show offers an insightful and entertaining conversation with one of the most talented comedians working today. Pete Holmes' humor and wisdom are on full display as he talks about his life, his work, and the power of comedy to bring people together.