It’s been 20 years since Rudy Giuliani was named Time’s Person of the Year - and his fêted time as mayor of NYC ended - and oh how the mighty have fallen.

“Sixteen hours had passed since the Twin Towers crumbled and fell, and people kept telling Rudy Giuliani to get some rest. The indomitable mayor of New York City had spent the day and night holding his town together,” read Time magazine’s December 2001 excerpt on Giuliani.

Another part read, “With the President out of sight for most of that day, Giuliani became the voice of America. Every time he spoke, millions of people felt a little better. His words were full of grief and iron, inspiring New York to inspire the nation.”

While he was once known as the tough Attorney for the Southern District of New York, a crime-busting prosecutor, and the two-term mayor who kept New York City going in the wake of the 9/11 terror attacks - that’s all changed.

All of these accomplishments were trumped (pun intended) by his relationship with former President Donald Trump, where he acted as his personal lawyer.

From there he racked up a pretty spectacular amount of glorious fails. We’ve rounded up some of Rudy Giuliani's most damning moments since he was named Time’s Person of the Year back in 2001. 

Borat caught Rudy Giuliani on the big screen

In the hilarious sequel to Sacha Baron Cohen's "Borat," Giuliani is seen being interviewed in a hotel suite by actor Maria Bakalova, who plays Borat’s 15-year-old daughter in the film. Giuliani’s appearance is certainly unexpected, but boy does it make for an Oscar-winning moment.

Bakalova, who is posing as a journalist, is seen at one point leading a Giuliani to a hotel room, and the former NYC mayor isn’t shy about his flirtation. Luckily for us, the hotel room with equipped with hidden cameras that catch Giuliani lying back on the bed and sticking his hand into his pants. At that moment, Borat crashes in and yells: "She 15! She too old for you!"

Sure, Giuliani defended himself in a lengthy Twitter thread, but the damage was done. He called the video "a complete fabrication" and claimed he was simply "tucking in shirt after taking off the recording equipment."

Cohen later responded in true Borat fashion by saying in a video: "I’m here to defend America's mayor, Rudolph Giuliani. What was an innocent sexy-time encounter between a consenting man and my 15-year-old daughter has been turned into something disgusting by fake news media."

The Four Seasons Total Landscaping press conference

How could we forget the viral press conference at the Philadelphia landscaping center? In case you need a refresher: then-President Donald Trump had announced on Twitter (you know, before he was banned) that Giuliani would hold a press conference at the Four Seasons. No...not that Four Seasons.

Instead of the five-star elegant hotel, Giuliani held the conference at Four Seasons Total Landscaping, located between Fantasy Island Adult Bookstore and the Delaware Valley Cremation Center in the middle of nowhere.

To make things worse, news broke that Joe Biden had officially been elected as the next President during Giuliani’s press conference. Leading to this marvelous meltdown:

"Oh my goodness! All the networks. Wow!" Giuliani said, "Networks don't get to decide elections. courts do."

Dripping hair dye

Oh, you thought the Four Seasons Total Landscaping was the worst that it got for Giuliani? You are much mistaken. In true Giuliani fashion, the former prosecutor outdid himself.

His subsequent press conference was dedicated to claiming election fraud and spurring lie after lie. And it appears as though his lies eventually caught up to him in the form of icky sweat.

Thus, a sweaty Giuliani began to ooze black hair dye down both sides of his face.

Rudy Giuliani's daughter spoke out against him

Even his daughter could no longer stand idly by and watch her dad fall deeper into disgrace.

Rudy Giuliani's own daughter, Catherine Giuliani, wrote a lengthy op-ed for Vanity Fair where she declared her intention to vote for Joe Biden and slammed her father.

The article, titled “Rudy Giuliani Is My Father. Please, Everyone, Vote for Joe Biden and Kamala Harris,” is pretty damning.

Some of it reads, "If being the daughter of a polarizing mayor who became the president's personal bulldog has taught me anything, it is that corruption starts with 'yes-men' and women, the cronies who create an echo chamber of lies and subservience to maintain their proximity to power.

She even took a shot at her father’s hair dye situation in a follow-up post aimed at Trump supporters that detailed how to accept they lost the election where she wrote, “Avoid charcoal products or anything with artificial dyes, which may result in your face oozing as you make false claims of voter fraud in Philadelphia, for example."

He might have asked for a pre-emptive presidential pardon

According to the New York Times, Giuliani discussed the "possibility of receiving a pre-emptive pardon" before Trump exited the White House. Why do the crime if you can’t do the time Rudy?!

While the Times specified the extent of Giuliani's criminal exposure were "unclear," people might remember how Giuliani found himself under federal investigation due to some allegedly shady business dealings in Ukraine, and his part as one of Trump’s closest allies.

Those who smelt it dealt it

We’re sorry but this viral moment was just too good not to include.

In early December 2020, Giuliani had continued his quest to overturn the results of the presidential election and headed to the courts as he said he would. But one particular moment at a Michigan court went viral for all the wrong reasons. Listen for yourself.

In a brief clip shared by HuffPost journalist Ryan Reilly on Twitter, Giuliani can be seen speaking when a loud fart can be heard. He hasn’t been confirmed as the culprit, but the attorney sitting beside him, Jenna Ellis, is spotted looking rather wide-eyed as the toot occurs.

Rudy Giuliani's law license is suspended

Just a couple of months after Giulani underwent a raid on his home, the New York Supreme Court suspended his license upon declaring that he had made "demonstrably false and misleading statements" regarding the 2020 presidential election, per CNN. The court ruling further found that Giuliani's "conduct immediately threatens the public interest and warrants interim suspension from the practice of law.”

The following month, in July 2021, Giuliani was also barred from practicing law in the nation's capital. As Forbes reported, the District of Columbia Court of Appeals similarly suspended Giuliani's license to practice law.

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