In a surprising turn of events, comedian Norm Macdonald's relentless pursuit of the perfect punchline, particularly targeting O.J. Simpson, ultimately led to him losing his dream job as the anchor of "Saturday Night Live's" Weekend Update. Macdonald's refusal to compromise on what he found funny and his unwavering focus on Simpson's trial for the murder of his ex-wife and a friend ultimately clashed with the higher-ups at NBC.

During his tenure as SNL's fake anchorman in the 1990s, Macdonald's comedic obsession with Simpson did not go unnoticed. Despite hints of potential trouble, Macdonald and his writing team were given the green light to continue writing jokes about the infamous trial, even though it caused friction at the executive level. Jim Downey, the comedy writer overseeing Weekend Update at the time, had to defend Macdonald's comedic choices against the disapproval of NBC executive Don Ohlmeyer, who happened to be a close friend of Simpson.

Despite the pushback, Macdonald's dry and deadpan delivery, coupled with jokes that were written to sound more like news stories than mere punchlines, resonated with audiences. Macdonald didn't seem to seek the audience's approval, relishing in the awkward silences that sometimes followed his jokes. However, his comedic sensibility clashed with the network's desire for a more upbeat and entertaining atmosphere on the show.

The breaking point came midway through the 1997-98 season when Ohlmeyer decided to replace Downey as the overseer of Weekend Update. Macdonald was offered the opportunity to stay if he made amends with the new team, but he declined, choosing loyalty to Downey over maintaining his position. As a result, Macdonald had already delivered his final O.J. joke on SNL.

Macdonald's connection to Simpson didn't end there. In the late '90s, he and his producing partner Lori Jo Hoekstra encountered the acquitted star while golfing, maintaining a cautious distance for the sake of their third companion, Kato Kaelin, a prosecution witness who stayed at Simpson's guesthouse on the night of the murders.

In later years, Macdonald attempted to secure an interview with Simpson for his sports show on Comedy Central in 2011. However, this interview never materialized, leaving the reasons behind its failure unclear. Macdonald's dedication and fearlessness in mocking Simpson were praised by former Weekend Update host Dennis Miller during a 2019 appearance on David Spade's talk show. Macdonald quipped that perhaps he was the greatest rusher to judgment, acknowledging the jury's verdict of Simpson's innocence.

Norm Macdonald's stint at SNL's Weekend Update will be remembered for his unyielding pursuit of comedic perfection, even at the cost of his dream job. His unwillingness to compromise on what he found funny, particularly when it came to O.J. Simpson, ultimately led to his departure from the show. Macdonald's impact on SNL's fake-anchorman legacy, alongside his idol Chevy Chase, remains significant, showcasing his talent as an anchor who looked and sounded like an actual newsman.