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He is known for his five seasons as a cast member on Saturday Night Live, which included anchoring Weekend Update for three years.
Early in his career, he wrote for the sitcom Roseanne and made appearances on shows including The Drew Carey Show and News Radio. Paste named him #31 on their The 50 Best Stand-up Comics of All Time.
Macdonald would occasionally deliver a piece of news, then take out his personal compact tape recorder and leave a "note to self" relevant to what he just discussed.
“Among many other things, this show was to be the return of Eddie Murphy,” Macdonald wrote.Current "Weekend Update" anchor and writer Colin Jost named Macdonald as a primary influence on Jost's own work behind the "Update" desk, explaining that Macdonald's tone was one that Jost grew up with in high school.Macdonald's version of "Weekend Update" often included references to prison rape, crack whores and the Germans' love of Baywatch star David Hasselhoff.The raw joke, a stellar example of Macdonald in his prime, was only seen by an audience during a rehearsal.Showing the famous photo of naked Vietnamese children running from a South Vietnamese napalm attack, Macdonald cracked, “In other news, Woody Allen is dating again!