John Oliver confirms that, yes, Rudy Giuliani has always been like that 

Except, as Oliver spelled out in relentless comic detail, “ill-advised and chaotic” has always been Rudy Giuliani’s jam. Like, “marrying a woman who was revealed to be his second cousin” ill-advised. Or “insulting a constituent about ferret ownership on his mayoral call-in show” chaotic. Or maybe “spending $50 million on a presidential campaign that netted him exactly zero delegates.” (Both ill-advised and chaotic.) And let’s not forget his overtly authoritarian and racist “tough on crime” policies as New York’s mayor, and his post-mayoral swamp-dive into the sort of corporate teat-suckling he later attacked Hillary Clinton for. But Oliver’s point was that, despite a brief reputational oasis as “America’s Mayor” post-9/11, Rudy Giuliani has always been egotistical, loose-lipped, fame-hogging, and all-around boorish and awful, which makes his current gig as Donald Trump’s mouthpiece make a lot of sense. Also, as Oliver noted, Giuliani’s self-promoting shamelessness saw him reduced to peddling hatefully stupid and unfounded Clinton conspiracy theories on Fox before soulmate in bigoted incompetence Trump scooped him from the bottom of the legal well after his latest lawyers ran screaming for the hills.

This being Last Week Tonight, and John Oliver being himself, this scrupulously researched character assassination could only conclude with a bit of creative horseplay. Just check out the newly purchased domains hillaryclintonillness.com, giuliani-security.com, and guiliani2024.com for Oliver’s signature brand of online rat-fuckery. Well, not rats, exactly. Oh, and Oliver concluded this week’s show by claiming that the unprecedented success of a previous prank means he’s closing up shop forever. Don’t worry about it. Probably.