In a recent episode of Conan O'Brien's talk show, "Conan O'Brien Needs A Friend," Jim Downey, former writer for Saturday Night Live, discussed the "anarchy" and brilliance of Norm Macdonald's "Weekend Update" segment. Downey highlighted how he and Macdonald crafted an update that was stripped down and punk-like, challenging the audience with edgy and smart humor.

According to Downey, Macdonald had the perfect look and intelligence to deliver complex jokes. With a clipped and precise delivery, Macdonald's comedy on "Weekend Update" was unlike anything else on television. Downey expressed admiration for Macdonald's ability to hold a punchline, allowing the audience to appreciate the humor fully.

One of the most memorable moments discussed was during the O.J. Simpson trial. Downey and Macdonald wrote sharp and self-deprecating jokes that cut through the media frenzy surrounding the trial. They aimed to challenge the audience with uncomfortable humor instead of resorting to easy laughs. Their jokes were often self-owned, adding an extra layer of depth to their humor.

Downey recalled a particular joke about Johnny Cochran holding up the knit cap found at the crime scene, with Macdonald quipping that it was O.J. Simpson's "lucky stabbing hat." The delivery and timing of the joke were impeccable, providing a prime example of Macdonald's unique comedic style.

Throughout their time working on "Weekend Update," Downey and Macdonald obsessively tweaked and refined their jokes, ensuring that every detail was perfect. Downey shared a joke about Penthouse Magazine's supposed alien autopsy photos, which initially focused on the ease of masturbating to them. However, Downey's addition of the word "surprisingly" transformed the joke into a rhythmically superior punchline.

The segment on "Conan O'Brien Needs A Friend" highlighted the incredible talent and chemistry between Downey and Macdonald. Together, they created a groundbreaking and iconic performance on "Weekend Update" that is still recognized today. Their dedication to crafting clever and boundary-pushing humor continues to resonate with fans of the show.

Overall, Downey's conversation with Conan O'Brien provides a fascinating insight into the creative process and comedic brilliance behind Norm Macdonald's time on "Weekend Update." Fans and comedy enthusiasts alike can appreciate the legacy of Macdonald's work and the lasting impact he made on the late-night talk show genre.