As Rudy Giuliani stood across from Will Ferrell while the comedian portrayed Janet Reno on "Saturday Night Live," the New York mayor took a fake punch to the gut and said he had to defend himself, vowing that the fictionalized version of the U.S. attorney general would "prepare to eat it, Giuliani-style!"

Giuliani got in a few good fake punches to the face during the impromptu boxing match on "Janet Reno's Dance Party," but he suffered a knee to the groin and a couple more punches to the gut that had the mayor ridiculously conceding that "Janet Reno is the boss of me," much to the delight of the SNL crowd in 1997.

The scene was one of many in pop culture in the 1990s and early 2000s that helped build up Giuliani as "America's mayor" - someone who could easily make a cameo on "Seinfeld" to talk about a nonfat yogurt scandal or show up on SNL to stand with first responders after the Sept. 11, 2001, terrorist attacks at a raw moment in the nation's history.

But the vibes have drastically changed in the past couple of decades for Giuliani, who has become a regular punchline for late-night hosts and comedians after repeatedly supporting and spreading Donald Trump's false claims that the 2020 presidential election was stolen. Giuliani, who was ordered on Friday to pay two Georgia poll workers who sued him for defamation $148 million, has been regularly roasted in recent years for moments such as the ill-fated news conference at Four Seasons Total Landscaping or getting pranked by Sacha Baron Cohen in "Borat Subsequent Moviefilm."

The comedic criticism has continued this past week, with "Daily Show" guest host Kal Penn. The actor noted how Giuliani's lawyer claimed that the more than $40 million in damages that Giuliani is being sued for in the defamation trial would "be the end of him."

"The end of Rudy Giuliani is, like, a best-case scenario," Penn said this week. "Why is Rudy's lawyer threatening the jury with a good time?"

While Giuliani repeatedly promised that he would use his defamation trial to explain why he falsely claimed that Georgia poll workers Ruby Freeman and Wandrea ArShaye "Shaye" Moss helped steal the 2020 election, he declined to take the stand on Thursday. Even though a judge in August found that his comments were defamatory and Giuliani agreed before trial not to contest that his claims were false, he still told reporters earlier this week that "everything I said about them is true."

Giuliani's choice not to testify was an opportunity for Michael Gottlieb, an attorney for the plaintiffs, to quote from the former mayor's memoir and remind Giuliani of who he once was: "Never pick on someone smaller than you. Never be a bully."

"Those are wise words," Gottlieb said. "If only Mr. Giuliani had listened."

Decades before the defamation trial, Giuliani was in on the joke.

It started in November 1993, after Giuliani defeated David Dinkins to become mayor of New York. "Seinfeld" had asked both the Giuliani and Dinkins campaigns to take part in an episode about a fictionalized version of that year's mayoral campaign involving a frozen yogurt shop that advertised its delicious product as nonfat. Depending on who won the election, either Giuliani or Dinkins would be in the episode that aired two nights later. Producer Tim Kaiser recalled in a "Seinfeld" DVD extra that there was some resistance from the Dinkins campaign for the Democratic mayor to participate but that Giuliani immediately agreed to do it.

"Giuliani's camp was in from Day 1, so we all became Republicans and were pushing hard for [him to win]," Kaiser recalled.

When Giuliani won, he took part in a faux news conference to address his high cholesterol.

"It's hard to understand because I've been doing everything I normally do. I've been watching my diet very carefully. I exercise regularly," Giuliani said. "My only indulgence, I guess, would be that I eat a lot of frozen yogurt. But it's nonfat."

Giuliani continued to have fun when he hosted SNL in November 1997 after he was reelected as mayor. While critics have regarded him as one of the worst hosts in the show's history, clips of Giuliani getting pummeled in boxing, beating up cast members with stickball bats and dressing up in drag to play an Italian grandmother won him praise.

He returned to SNL under very different circumstances in 2001, 18 days after 9/11. Giuliani, who had won widespread acclaim for his handling of the attacks and would soon be named Time magazine's person of the year, was asked by SNL executive producer Lorne Michaels to make a speech during the show's cold open.

"We will not let our decisions be made out of fear," Giuliani said alongside police officers and firefighters who had been working for days at Ground Zero. "We choose to live our lives in freedom."

Michaels also had a question for the mayor on Sept. 29, 2001: "Can we be funny?"

"Why start now?" Giuliani replied, giving way to the biggest laugh of an emotional night.

Michael Schur, an SNL writer who went on to create "The Good Place," recounted in a Rolling Stone oral history in 2021 that Giuliani's line was the best joke during the writer's time on the show.

"It was so smart that [Michaels] gave the punchline to Giuliani, because everyone loved Giuliani so much in that moment," Schur said.

That would change as the years went by and as Giuliani drifted further to the right. It only intensified in 2020, when, in a stretch of days, he was captured on a hidden camera in an unflattering position in a scene that made the "Borat" sequel and took questions from reporters at Four Seasons Total Landscaping about the election he falsely claimed Joe Biden had stolen. While he appeared on SNL shortly after his failed 2008 presidential campaign, Giuliani would come to be portrayed in recent years by then-cast member Kate McKinnon, who relentlessly mocked Trump's personal attorney as he spread false claims about the 2020 election.

It has continued this past week on late-night TV, as NBC's Seth Meyers pointed out how Giuliani has been scolded for his behavior during the defamation trial.

"A judge actually had to tell Rudy Giuliani, a former federal prosecutor, in the courtroom, 'Your words have to make sense,'" Meyers joked. "It's one thing for a judge to say, 'Your objections have to be relevant,' or, 'Your objections have to be in good faith,' but you know you're in trouble when a judge says, 'What ... are you saying?'"

Giuliani has mostly not responded to the criticism from the comedians who once sought him out, but he could not ignore Penn's comments about him on "The Daily Show." After he called Penn, a former Obama administration official, a "slob," Giuliani wrote on X what he thought about the segment calling for "the end of Rudy Giuliani."

"Definitely not funny!"

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Rachel Weiner, Tom Jackman and Spencer S. Hsu contributed to this report.