Dripping hair dye to Four Seasons Total Landscaping: Rudy Giuliani’s best worst moments

Rudy Giuliani has undergone an unprecedented trajectory in politics.

He went from “America’s Mayor,” praised as a hero in his handling of the aftermath of 9/11 in New York City, to Donald Trump’s attorney, accused of spreading election fraud claims after the 2020 election.

He has made infamous appearances in TV shows and movies and notably gave a press conference with hair dye streaking down his sweaty face.

The former mayor has also found himself embroiled in a series of legal headaches. He faces criminal charges in the sprawling Fulton County RICO case, outrageous allegations of sexual assault by his former assistant Noelle Dunphy in New York, and a lawsuit from his attorney for allegedly failing to pay his legal fees.

Now, he has been told to pay a total of $148m to two Georgia election workers he repeatedly defamed by falsely claiming they were involved in voter fraud during the 2020 election, something that left them facing death threats and racist abuse. Mr Giuliani called the award “absurd”, said he had “no regrets” and promised to appeal the ruling.

In light of his recent headlines, here is a look back at some of Mr Giuliani’s most outlandish moments.

Hair dye

The post-election crusade from Donald Trump’s team after he lost the 2020 election was oozing with memorable moments — perhaps none other than the hair dye melting from Mr Giuliani’s face during a press conference.

As Mr Giuliani was vehemently contesting the election results from a podium in Washington DC, the combination of perspiration and hair dye merged to create pseudo-side burns.

Borat Subsequent Moviefilm

The satirical “Borat Subsequent Moviefilm” captured the real Giuliani meeting with a fake journalist — who he seemed to think was legitimate — in a New York City hotel room. The fake journalist, Borat’s daughter, conducted an interview before asking him to get drinks in his bedroom.

Viewer discomfort ensued. Secret cameras helped create one of those moments where viewers couldn’t watch but also couldn’t look away: Rudy Giuliani with his hands down his pants.

Four Seasons Total Landscaping

The press conference that will forever live in infamy — not only for its contents, but also for its location: Four Seasons Total Landscaping. Mr Giuliani took the podium in Philadelphia in November 2020 to discuss the city’s alleged “sad history of voter fraud.”

One can only imagine this was a Google error. Someone seemingly tried to book the swanky hotel but instead called the landscaping company. The world may never know, but is forever grateful.

Masked Singer

This one was not on the bingo card. During the 2022 season of the kooky singing competition show, “The Masked Singer,” in which celebrities sing while dressed in costume and famous judges try to guess who is behind the costume, a Jack-in-the-Box player was eliminated.

Judges tried to place the voice. Was it Robert Duvall? Joe Pesci? The mask came off, revealing the one and only: Rudy Giuliani.

“Well Mr Giuliani, with all of the controversy that’s surrounding you right now, I think it surprises us all that you’re here,” host Nick Cannon said after the reveal.

As he sang “Bad to the Bone,” judges Ken Jeong and Robin Thicke walked off the stage — seemingly in protest.

The ‘Bill Clinton’ treatment

In May, Mr Giuliani’s ex-employee Noelle Dunphy accused him of sexual assault and harassment.

The bombshell lawsuit provided outrageous details, like her claim that “he often demanded oral sex while he took phone calls on speakerphone from high-profile friends and clients, including then-President Trump. Giuliani told Ms Dunphy that he enjoyed engaging in this conduct while on the telephone because it made him ‘feel like Bill Clinton.’”

Ted Goodman, a spokesperson for Mr Giuliani, told The Independent in May that his employer “unequivocally denies the allegations raised by Ms Dunphy”.

Matt Damon

As part of her court filing, Ms Dunphy also submitted transcripts of recordings of Mr Giuliani. In one transcript dated 2019, he seems to get confused about celebrities — and then insults one, and then some.

According to the transcript, Ms Dunphy asked: “Who were the other Republicans who are celebrities?”

Mr Giuliani replied, “Ain’t too many. Brad – not Brad Pitt. The other guy that looks like him.”

She asked if her boss meant Bradley Cooper before she landed on Matt Damon, who is “very liberal.”

Her boss strangely replied, “No, Matt Damon is a – Matt Damon is a f**. Matt Damon is also 5’2, Eyes are blue. Coochie-coochie-coochie-coo.”

It should be noted that not only does the actor’s IMDB page mark his height as 5ft 10in tall, but Mr Damon has been married to Luciana Barroso since 2005, and the pair share four daughters. It’s unclear why Mr Giuliani seemed to have a vendetta against the A-lister.

The airport shave

In August 2021, videos captured Mr Giuliani sitting inside the Delta One lounge at New York’s JFK Airport.

While most people tend to read or do crosswords or play games on their phones while waiting for a flight, Mr Giuliani appeared to be shaving time by doing the unthinkable in public: he started shaving his face.

He scraped his razor up and down his face. Between this and the hair dye incident, nothing is sacred.

Moment that Joe Biden won the 2020 election

Speaking at a news conference on 7 November 2020, standing in front of rows upon rows of “Trump 2020” signs, Mr Giuliani learned that Mr Biden won the election.

“Who was it called by?” Mr Giuliani asked, hopefully.

“All the networks” called the election for Joe Biden, someone in the media replied.

No amount of money could have predicted that Mr Giuliani would react how he reacted: “Oh my goodness! All the networks? Wooooow!”

He threw his hands up to the sky, yelling, “All the networks! We have to forget about the law! Judges don’t count!”

He continued, now talking to the press, “Don’t be ridiculous. Networks don’t get to decide elections. Courts do.”