Rudy Giuliani’s political career has certainly followed a highly unusual trajectory.
He went from being known as “America’s Mayor,” praised as a hero for his handling of the aftermath of 9/11 in New York City, to a rather more infamous stint as Donald Trump’s personal attorney, accused of spreading voter fraud lies after the 2020 election.
He has made infamous appearances on TV shows and in movies and unforgettably gave a press conference with dark 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 alongside Mr Trump, allegations of outrageous 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.
Most damningly, he has been ordered 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 – an untruth 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 against him but has nevertheless also been forced to file for Chapter 11 bankruptcy and complain that his creditors desire to sell off his Florida condo would leave him to “join the ranks of the homeless”. A judge has so far declined to rule on whether Mr Giuliani can be compelled to sell his Palm Beach property, but warned that “draconian requests” from the committee could ensue.
In light of his recent run of disasters, here is a look back at some of Mr Giuliani’s most outlandish moments from a long career in the public eye.
Hair dye
The post-election crusade from Mr Trump’s team to overturn the result of the 2020 election after he lost oozed with memorable moments but perhaps none was more extraordinary than the site of hair dye treacling down 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 two black streaks of pseudo-side burns, not doing much for his demand to be taken seriously.
Borat Subsequent Moviefilm
The satirical comedy sequel Borat Subsequent Moviefilm entrapped the real Mr Giuliani into a meeting with a fake journalist (Maria Bakalova) — whom he seemed to think was legitimate — in a New York City hotel room.
The fake reporter, Borat’s daughter Tutar, conducted an interview before asking him to get drinks in his bedroom.
Some serious viewer discomfort ensued.
Secret cameras helped create one moment in particular that viewers couldn’t watch but also couldn’t look away from: Mr Giuliani with his hands down his pants as he lay on a hotel bed.
He later claimed he was merely adjusting his trousers.
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, an unassuming Philadelphia garden centre apparently booked in error.
Undaunted despite surely having realised the blunder, Mr Giuliani duly took to a makse podium in the store’s car park in November 2020 to discuss the city’s alleged “sad history of voter fraud.”
One can only imagine that some form of warped Google error had occured, with an unlucky aide attempting to book the luxury hotel of the same name and getting it wrong.
It was Mr Giuliani’s decision to carry on regardless that made the whole thing so farcical, however.
The 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 disguise, a Jack-in-the-Box player was eliminated.
Judges tried to place the voice. Was it Robert Duvall? Joe Pesci?
Oh no. When the mask came off, it was none other than Rudolph Giuliani himself.
“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 2023, 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.
The 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,” a reporter 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 as a whole: “Don’t be ridiculous. Networks don’t get to decide elections. Courts do.”
