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‘The Daily Show’ Charts Rudy Giuliani’s Sketchy Rise And Boozy Fall In A New Mini-‘Dailyshowography’

Things haven’t been good for Rudy Giuliani in a long time. In fact, they keep getting worse. Not long after his disastrous surprise appearance on The Masked Singer, the fallen former “America’s Mayor” has come up again thanks to the Jan. 6 hearing, where people reminded the public that he was reportedly three sheets to the wind on Election Night, giving then-client Donald Trump some garbage advice. (He listened, of course.)

Now this. On Tuedsay night’s episode, The Daily Show tackled Rudy’s truly surreal life and career in their new “Dailyshowography,” which has previously covered the likes of Lindsey Graham, Ted Cruz, Vladimir Putin, and more. It starts with his birth to an alleged mob enforcer who did time in Sing Sing, shows his early aspirations towards priesthood (“Giuliani almost became a man of the cloth, instead of a man of sweaty handkerchiefs,” narrator Desi Lydic says over shots of him mopping his forehead), and eventually marrying his childhood sweetheart: his second cousin. At one point George H.W. Bush publicly mangles his surname.

It shows Giuliani moving through the Reagan administration en route to being the mayor of New York City, which he only nabbed after coming after the city’s first Black mayor, David Dinkins — and after helping foment the 1992 City Hall riot comprised of off-duty NYPD officers. (Lydic remarks that “getting a crowd to storm a government building would be good practice for him,” cutting to images from Jan. 6).

Once in office, Giuliani cleaned up the dirty town using “some of the most iconic anti-crime tactics of the time, like stop and frisk, broken windows policing, sexual assault with a broom handle, and shooting an innocent guy so many times Bruce Springsteen wrote a song about it.” (That would be “American Skin (41 Shots).”)

His big break is his calm leadership after the September 11 attacks, but even that didn’t help his presidential aspirations leading up to the 2008 election. He eventually gloms onto Donald Trump, seen in a jokey video from the ’90s sexually harassing a cross-dressing Rudy, who gives him a big slap. Eventually Giuliani would burn his reputation to the ground for Trump, who repaid the favor by leaving him high and dry.

Eventually they conclude that Giuliani is always “standing tall, through 9/11 or a blood alcohol of 9.11.”

You can watch the Giuliani “Dailyshowography” in the video above.

(Via The Daily Beast)