Duterte, a former prosecutor, has been making headlines throughout the cycle for his brash and extreme stance on crime. If elected, Duterte has promised to kill all the criminals in the country if he becomes president. He is a self-proclaimed womaniser and speaks often of his sexual exploits.
Oliver introduced Duterte as a "colourful character, to say the least," before playing an Al Jazeera segment showing the mayor at a recent mass wedding. From the stage, he offered himself to the brides as a wedding gift.
"I don't have money to give, but I could give your wives something else, and this is for the wives only," Duterte says. "Men, I'm sorry, but you don't get anything, because I'm not a queer."
Oliver continues.
"That's just the tip of the iceberg," he says. "Duterte routinely kisses his female supporters, once called the Pope 'a son of a bitch,' all of which has earned him a reputation as the 'Trump of the East,' a title previously held by a burnt wonton covered in scarecrow pubes.
"Now, Duterte has also suggested if elected he would kill five criminals every week, which may not be an idle promise. Since he's been mayor, extrajudicial death squads have reportedly killed over 1000 people, and while he denies any involvement in that he does admit he's got blood on his hands."
Then Oliver cuts to a clip from a Duterte interview with Rappler reporter Maria Ressa.
"So no qualms about killing killers?" she asks him.
"Yes, of course, I must admit I have killed," Duterte responds. "Three months early on, I killed about. . . three people."
"I'm sorry, about three people. That's not good!" Oliver shouts when the clip stops playing. "Not knowing how many people you killed is like not knowing how many Vicodin you took. If you don't know the exact number, the answer is way too . . .. many."
"And yet incredibly, none of this has hurt him," Oliver says.
At the time of the show's taping, Duterte held an 11-point lead over his opponents.
That's despite what may have been the Mayor's most extreme comments of the campaign, which Oliver queued up next.
"Duterte has seemed like he is trying to test the limits on basic human decency," the host said.
Last month during a rally in Quezon City, Duterte brought up an incident that occurred at the Davao jail during his first term as Mayor in 1989, when an Australian missionary named Jacqueline Hamill was held hostage by inmates, who gang raped her before they slashed her throat.
"I looked at her face, son of a b****, she looks like a beautiful American actress. Son of a b****, what a waste," Duterte said. "What came to mind was, they raped her, they lined up. I was angry because she was raped, that's one thing. But she was so beautiful, the mayor should have been first. What a waste."
Like much of the Internet and the Australian Embassy in the Philippines, Oliver was not amused.
"And if any part of you is thinking, was that some sort of horrific joke? Please know he meant every word of it."
Then Oliver cut to a clip of Duterte denying allegations that his comment was said in jest and telling reporters instead that he was merely repeating at the rally what he initially said in 1989: "It was not a joke. I said it in a narrative, I was not smiling. I was just talking plain sense."
Next, Oliver called the Mayor a monster.
"And yet incredibly, incredibly, this man is ... probably going to get elected president tomorrow, which isn't just terrifying for the Philippines, because it means that in just a year's time, we could be treated to this", he said - pointing to an edited image of Trump and Duterte shaking hands in the Oval Office - "as an official state visit."
Warning: Video contains graphic language.
Video: https://youtu.be/SLo67AdKTQ0
