Conan welcomes Jim Downey, a legendary comedy writer from Saturday Night Live, known for his sharp wit and contributions to classic sketches. They dive into Downey's favorite SNL moments, recount hilarious behind-the-scenes stories, and reflect on performances alongside Daniel Day-Lewis in 'There Will Be Blood.' The conversation touches on mastering Weekend Update with Norm Macdonald and navigating the fine line between humor and sentimentality in comedy, providing a delightful insight into the art of laughter.

Jim Downey, SNL writer and producer, talks about writing sketches and impersonations. They discuss creating caricatures of Al Gore during his presidential campaign and contrasting portrayals of George H.W. Bush and Donald Trump. They also share a long-running practical joke and their experience writing an ad for a change bank.

In this lively conversation, Jim Downey, a celebrated SNL writer and producer known for his sharp political comedy, shares memorable anecdotes from his tenure alongside Al Franken. They dive into the art of crafting political sketches, emphasizing the blend of humor and accessibility. Jim recalls iconic sketches featuring George W. Bush and reveals the spontaneous nature of live shows. With plenty of laughs, they reflect on political ideologies and discuss the vital role of humor in fostering creativity in comedic writing.