- September 9, 2005: In the last New Rule of the night, titled "George of the Bungle", Bill gives a hilariously scathing "The Reason You Suck" Speech to then-President George W. Bush.
- March 25, 2011: Bill uses the final New Rule of the night, "Barry, White", to introduce the fictitious GOP candidate for the 2012 presidential election: Karab Amabo, an American who is the complete opposite of Barack Obama in almost every way except gender, effectively ridiculing the excessive Commander Contrarian attitude which the GOP holds towards Obama.
- May 6, 2011: After Osama Bin Laden's death, Bill takes one last potshot at the 9/11 truthers in the New Rule "Truther Consequences".
Bill: New Rule: Conspiracy theorists who are claiming that we didn't really kill Bin Laden must be reminded that they didn't think he did the crime in the first place!
- In the New Rule "The Party of Stinkin'", Bill mocks the Republicans for the fact that Obama has done everything they said they do best even better.
- July 29, 2011: In the New Rule "The Hide Amendment", Bill gives an "It Gets Better"-style monologue about socialism.
- August 5, 2011: In the New Rule "Cuckoo Bloc", Bill humorously recommends that Democrats fight the nutty far-right Tea Party by recruiting nutty far-left Americans into a party-within-a-party called the Donner Party, saying "We will literally eat each other before we give an inch!".
- March 23, 2012: Bill dubs Mitt Romney "The Least Interesting Man in the World", spoofing Dos Equis' "The Most Interesting Man in the World" commercials, in a monologue about oversensitivity and constant apologizing in both mainstream media and politics.
Bill: He says corporations are people because compared to him, they are. When Ambien can't sleep, it takes him. He once masturbated over the great everyday values at Sears. Paint watches him dry. He doesn't always drink beer, but when he does... no, wait, he never drinks beer, because he's the least interesting man in the world! Stay boring, my friends.
- September 7, 2012: In the New Rule "Born Supremacy", Bill chastises upper-class conservatives like Mitt Romney, Paul Ryan and Donald Trump for acting like their lives were so hard when they were younger, going into detail of what their lives would've been like if they'd never been born into such comfortable statures, in a segment called "It's a Significantly Less Wonderful Life".
- April 25, 2014: In the New Rule "November Reign", Bill urges California liberals to Stop Being Stereotypical, because their Political Correctness Gone Mad is fueling the far right's paranoia. He cites a case of atheists protesting the presence of a Christian cross, saying "You're atheists, not vampires!"
- June 13, 2014: In light of the legalization of marijuana in states like Colorado, Bill humorously offers some dos and don'ts for novice potheads.
- January 23, 2015: As the 2016 presidential primaries are approaching, Bill offers wealthy conservatives a "buyers' guide" of likely GOP nominees. As he discusses Jeb Bush, Bill says "In terms of brand loyalty, Hillary's like if your last car was a Camry, whereas Jeb's like if your last car was... a clown shoots you out of a cannon."
- March 25, 2016: Since the 2016 Republican presidential field has practically been narrowed down to the two most despised candidates, Donald Trump and Ted Cruz, Bill has to choose who he'd rather see as president. After much deliberation ("Trump is like Ebola: he’ll violently kill you right away. Cruz is like Zika: we won’t see the damage until future generations.") he picks... Cruz, rinsing his mouth with a large bottle marked "BLEACH" after his decision.
- In 2013, Bill jokingly offered Donald Trump $5 million if he could produce his birth certificate and prove that he is not the offspring of a woman and an orangutan. Trump responded with a lawsuit citing defamation and demanded an apology, which Bill laughed off until Trump finally backed off. During the 2016 election, Bill has occasionally brought up the story. In May 2016, once Bill put up a picture comparing Trump to an orangutan, the audience lost its shit. In October 2016, Bill brought up the story again, and this time put it as asking Trump to prove that "his mother did not, in fact, fuck an ape." Bill brought it up again in August 2017 to just as many jeers as he clarified he wanted Trump to prove he wasn't half-orangutan.
- In July 2017, Bill interviewed one of the leaders of Breitbart. As the website is known for being what Steve Bannon himself called "the platform of the alt-right (cough cough Neo-Nazis)" and Bill's live audience generally skews liberal, Bill takes a moment to quickly ask his audience to "be nice" like a parent asking their child to be nice to a relative they hate at a family gathering.
- In August 2017, in the wake of the firing/resignations of several Trump administration officials — Sean Spicer, Reince Priebus, Anthony Scaramucci, Steve Bannon, and Sebastian Gorka — in just a matter of weeks, Bill joked that "the bodies [were] really piling up outside the White House".