1993–1998: Saturday Night Live
Macdonald joined the cast of NBC's Saturday Night Live (SNL) television program in 1993, where he performed impressions of Larry King, Burt Reynolds, David Letterman, Quentin Tarantino, Clint Eastwood, Charles Kuralt, and Bob Dole, among others. The following year, during the show's twentieth season, Macdonald began anchoring the news satire segment Weekend Update.
His version of Weekend Update often included running jokes about prison rape, "crack whores", and the success of American actor-singer David Hasselhoff in Germany. Macdonald would occasionally deliver a piece of news before taking out his personal compact tape recorder and leaving a "note to self" relevant to what he just discussed. He commonly used actor-singer Frank Stallone as a non-sequitur punchline and absurdly blamed him for such events as toxic waste or high unemployment rates. Frank Stallone took no offence, later stating: "He wasn't really attacking me, it was just randomly thrown in there". Nonetheless, Macdonald stopped the Frank Stallone jokes after a 1997 request from Sylvester Stallone, Frank's brother, who was guest host for SNL.
On the Weekend Update aired on February 24, 1996, Macdonald joked about John Lotter's sentencing for the murders of Brandon Teena and two others:
And finally, in Falls City, Nebraska, John Lotter has been sentenced to death for attempting to kill three people in what prosecutors called a plot to silence a cross-dressing female who had accused him of rape. Now, this might strike some viewers as harsh, but I believe everyone involved in this story should die.
The comments were met with sharp criticism from activist groups, including The Transexual Menace, who threatened to picket SNL. Upon reviewing the show, NBC agreed the line was inappropriate and should not have aired, and said it would ensure that similar incidents would not happen in the future.
After the announcement that Michael Jackson and Lisa Marie Presley planned to divorce, Macdonald joked about their irreconcilable differences on Weekend Update. "According to friends, the two were never a good match. She's more of a stay-at-home type, and he's more of a homosexual pedophile." He followed this up a few episodes later with a report about the singer's collapse and hospitalization. Referring to a report that Jackson had decorated his hospital room with giant photographs of Shirley Temple, Macdonald added: "But don't get any ideas: Michael Jackson is a homosexual pedophile."
In early 1998, Don Ohlmeyer, president of NBC's West Coast division, had Macdonald removed as Weekend Update anchor, citing a decline in ratings and a drop-off in quality. He was replaced by Colin Quinn at the Weekend Update desk beginning on the January 10, 1998, episode.
Macdonald believed at the time that the true reason for his dismissal was his series of O. J. Simpson jokes during and after the trial, in which he frequently called him a murderer; Ohlmeyer was a good friend of Simpson and supported him during the proceedings. After being removed from the role, Macdonald went on CBS' Late Show with David Letterman and Howard Stern's syndicated radio show. In both appearances, the hosts accused Ohlmeyer of firing him for making jokes about Simpson. The jokes were written primarily by Macdonald and longtime SNL writer Jim Downey, who was fired from SNL at the same time. Downey pointed out in an interview that Ohlmeyer threw a party for the jurors who acquitted Simpson.
Ohlmeyer claimed that Macdonald was mistaken, pointing out he had not censored Jay Leno's many jokes about Simpson on The Tonight Show. Ohlmeyer stated he was concerned that ratings research showed people turning away from the program during Macdonald's segment; likewise, network insiders told the New York Daily News that Ohlmeyer and other executives had tried several times to get Macdonald to try a different approach on Update.
Macdonald remained on SNL as a cast member, but he disliked performing in regular sketches. On February 28, 1998, in one of his last appearances on SNL, he played the host of a fictitious TV series titled Who's More Grizzled?, who asked questions from "mountain men", played by that night's host Garth Brooks and special guest Robert Duvall. In the sketch, Brooks' character says to Macdonald's character, "I don't much care for you," to which Macdonald replies, "A lot of people don't." He was dismissed shortly thereafter.
The situation re-ignited in early June 1998 when Ohlmeyer prevented NBC from airing advertisements from Metro-Goldwyn-Mayer for Macdonald's new film Dirty Work out of retaliation for what he saw as Macdonald's disparaging SNL and NBC with Letterman and Stern. Robert Wright, Ohlmeyer's boss, later overturned the decision not to show ads for the movie on NBC, but did leave in place the ban on playing it during SNL. Macdonald continued to insist that he did not personally dislike Ohlmeyer but that Ohlmeyer hated him.
Macdonald complained to the New York Daily News about NBC's removal of advertising for his film, calling Ohlmeyer a "liar and a thug." He claimed never to have badmouthed SNL or Michaels, who he felt had always supported him. Macdonald pointed out that he had only taken issue with Ohlmeyer, whereas the people taking shots at NBC and SNL were Letterman, who wanted Macdonald to come to CBS, and Stern, who wanted him to join his show opposite SNL. Macdonald also asserted that Ohlmeyer's influence had resulted in the cancellation of promotional appearances for his film on WNBC's Today in New York, NBC's Late Night with Conan O'Brien, and the syndicated Access Hollywood (a joint venture between 20th Century Television and NBC). The shows that Macdonald named denied being influenced by Ohlmeyer. Macdonald said Ohlmeyer was "about a thousand times more powerful than I am. It's difficult for anybody to take my side in this. This guy should get a life, man."
Members of the media found irony in the situation, as Dirty Work was promoted as a "revenge comedy." When an interviewer pointed this out, Macdonald said: "It would be good revenge if everybody went and saw this movie if they want to get revenge against Don Ohlmeyer for trying to ban my ads." In a Late Show with David Letterman interview, Macdonald stated that after being dismissed from anchoring Weekend Update and leaving SNL, he could not "do anything else on any competing show."
In later years, he came to the conclusion that Ohlmeyer had not removed him from Update for his Simpson material; rather, he felt he was removed because he was seen as insubordinate: "I think the whole show was tired of me not taking marching orders. Lorne would hint at things... I'd do Michael Jackson jokes. And Lorne would say, 'do you really want a lawsuit from Michael Jackson?' And I'd say, 'Cool! That'd be fuckin' cool, Michael Jackson suing me!'" Elsewhere, Macdonald would concede, "In all fairness to him, my Update was not an audience[-]pleasing, warm kind of thing. I did jokes that I knew weren't going to get bigger reactions. So I saw [Ohlmeyer's] point. Why would you want some dude who's not trying to please the audience?"
Macdonald returned to Saturday Night Live to host the October 23, 1999, show. In his opening monologue, he expressed resentment at being fired from Weekend Update, and then he concluded that the only reason he was asked to host was because "the show has gotten really bad" since he left.