Norm Macdonald collage — Jordan Sellergren / Little Village

Comedian Norm Macdonald passed away Tuesday, Sept. 14, at age 61.

If you were born in the last millennium, you know Norm Macdonald. He was on Saturday Night Live from 1993-1998, including as the fake anchor on the “Weekend Update” news segment from 1994 to ’97. The style of humor that Macdonald brought to that job set the standard for every performer that took his seat afterwards.

Away from Saturday Night Live, he was very much in the mold of the American male comedians that came up in the 1970s. In the wake of Lenny Bruce’s comedy, and especially the stand-up of Richard Pryor, the old rules about “blue” material went out the window, and Macdonald embraced the freedom offered to be as explicit and crude as possible in search of laughs.

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Riding on his SNL fame, Macdonald was booked in 1997 for a big charity comedy event in Hancher Auditorium, in conjunction with the AEGON Advantage Golf Tournament. He and the two other comedians on the bill (Jim Breuer and Darrell Hammond) were scheduled to perform and then play golf in the golf tournament the next day. The people who booked the show apparently didn’t bother to research Macdonald’s standup, which at that time was both incredibly funny — and wildly inappropriate for a Hancher audience that included young children.

Macdonald, for his part, did not read or chose to ignore the part of his contract which asked for family-friendly comedy, without sexual material or profanity. After the event, Athletic Department spokesman Rick Klatt told the Cedar Rapids Gazette that they were assured during contract negotiations that Macdonald would “meet guidelines.” But Macdonald took the stage and did his usual stand-up set with no regard for the sensitivities of the audience. According to the Daily Iowan, “MacDonald frequently used the word ‘fuck,’ described his own masturbation habits and offered his opinions on anal sex between homosexual men.”

As people began booing and leaving in droves, Macdonald quipped, “What do you want me to talk about — losing my luggage at the airport?” Daily Iowan reporter Kevin Ho also wrote, “His jokes about women having sex with pigs also appeared to offend the audience.” At the time, seeing that on the front page of the Daily Iowan was as funny to me as any joke Macdonald could have told.

Linn County Supervisor Ben Rogers was there that night with his mother and younger brother.

“I remember people getting up and streaming out,” he said. “We stayed because we just wanted to see how it all unfolded … I just remember thinking he was either on drugs, he was drunk or he made a bet with the [Saturday Night Live] cast members who could be the most offensive.”

When asked what it was like to see an event like that with his mother, he laughed and said, “It was awesome! You knew you were watching something special you just didn’t know in what context. I was 17, my brother was 15. I’m just really happy we all decided to stay. There wasn’t anything that was going to offend us where we would feel the need to walk out … I felt sorry that people were leaving. Comedy is not for everybody and maybe Norm’s comedy wasn’t but on that night, for me, it absolutely was. You knew you were seeing something different.”

The University of Iowa Men’s Athletic Department issued a formal apology to, it seemed, the whole state of Iowa for Macdonald’s performance, and they disinvited him from the golf tournament the next day. There was plenty of blame to go around: Macdonald’s unwillingness to read the room and the Athletic Department for disastrously misjudging what kind of a comedian he was. The 20 percent of the Hancher audience that remained through the end of his set reportedly clapped and cheered.

It’s hard not to be amused at the whole debacle. Even in 1997, Iowa — neither the state nor the university — was not connected to the broader American culture in the way that both are now. One could easily be familiar with Macdonald’s “Weekend Update” appearances and not have any clue that he was so foul-mouthed. Many Iowans were still living in a world that simply didn’t include cracking jokes about anal sex.

Some Iowans still shudder to think of L’Affair Macdonald. Never bring it up if you’re talking to people in the UI Athletic Department! But others look back fondly at his fearless commitment to completely horrifying an audience. His check had no doubt already cleared and he dined out on that story for years afterwards. So no harm done to Norm. He blithely sailed away from Iowa, never (to my knowledge) to return.

The saddest part of the whole mishegoss is that most Iowans completely missed the genius of Macdonald’s humor. He styled himself as an affable, perpetually smiling Will Rogers sort of character. His delivery was intentionally at odds with his content; he had a penchant for saying unbelievable filthy things in the same tone of voice one might talk about taking the kids out for ice cream.

On TV talk shows, he’d have to tone down his language, but he would still say things that the host reacted to with mock horror. He was an old hand at skirting the strictures of network television censorship. But “blue” comedy aside, he was the virtuoso of long shaggy dog stories, in which he would seem to get lost in a Tristram Shandy-like maze of asides, digressions and misdirection.

Sometimes he clearly went too far, as in his comments on the murder of trans man Brandon Teena, saying that he “deserved to die.” But his homophobic extremes barely dented his popularity. (Although his repeated statements that Michael Jackson was a “homosexual pedophile” and calling OJ Simpson a murderer before his conviction may have been the real reason he was fired from SNL in 1998.) In recent years he’d gotten in trouble for going after queer comedian Hannah Gadsby and defending his longtime friends Rosanne Barr and Louis C.K.

The Norm Macdonald persona was at once funny, horrible and deeply, deeply weird. He loved using stylized, stilted language, awkward rhythms and long uncomfortable pauses that tested the audience’s patience as much as Andy Kaufman did. But in the end he always brought it home with a punchline that in no way earned the laugh it got, except by finally putting the joke (and the audience) out of its misery.

Part of his charm was that he portrayed a comedian who seemed really bad at his job. It’s hard enough to be funny, harder still to be really funny while being unfunny on the surface. That might be why his comedy is polarizing; some people don’t see the extra layer of irony built into his act. His faultless timing masqueraded as a series of awkward, lurching sentences punctuated with uncomfortable silences. Whatever he was like in his private life, his comedy persona was complex and layered.

When Jim Henson died, many people remarked that it was like Kermit dying. Macdonald dying means the end of “Norm Macdonald” — that goofy, awkward, slapdash comedian who made people laugh and feel uncomfortable at the same time.