While the Duke of York's royal life may have long been controversial, he also earned regard as the "Playboy Prince" who fought with bravery and distinction in the Falklands.
But now the Queen's second son will be best known as the Windsor who stepped down from royal duties amid the scandal surrounding Jeffrey Epstein, a disgraced financier who died in August awaiting trial on sex trafficking charges.
As a young man, he was one of the world's most eligible bachelors.
He was linked to a string of beautiful women, earning himself the nickname "Randy Andy" in the process.
He married and divorced the bubbly, flame-haired Sarah "Fergie" Ferguson, who herself has generated some of the most humiliating royal scandals of modern times.
The duke remained on good terms with his ex-wife Sarah, Duchess of York who always refers to him as her "bestest friend", and he has a close bond with their daughters Princesses Beatrice and Eugenie.
The duchess still lives at Andrew's home, Royal Lodge, in Windsor Great Park, and there is frequent speculation they will remarry.
Andrew can be charming, entertaining and polite, but he is also said to be abrasive and rude.
Royal biographer Sarah Bradford once described him as "an uncomplicated soul, rumbustious, a little spoiled and more than a little arrogant".
Used to getting his own way, he is said to insist that even his closest friends call him "Sir".
When a newspaper reporter managed to breach Buckingham Palace security to get a job as a footman, he said the Duke of York would greet the servant bringing his cup of tea with either "Good morning" or "F*** off" depending on his mood.
Even his mother is said to have once observed that her middle son is "not always a ray of sunshine".
But he is seen as the more jocular of his siblings and is fond, like many of his family, of playing practical jokes.
"Rude" food presented in a suggestive manner is said to cause him much amusement at the dinner table.
His room used to and may still contain a pillow bearing the motto "Eat, Drink, Remarry" and a toy replica of Monkey, the mascot of the former company ITV Digital, which he hid in a different place each day to amuse the staff.
The Prince of Wales is reported to have said of his brother: "He's like a fizzy drink that has been shaken up and the top taken off."
Unlike Charles, Andrew grew up free from the constraints of one day having to be king.
But being the spare to the heir means his less defined place within the Royal Family has come under intense scrutiny.
Andrew Albert Christian Edward, the third child and second son of the Queen and the Duke of Edinburgh, was born at Buckingham Palace on February 19 1960.
He arrived after a gap of almost 10 years between him and Princess Anne and became the first child to be born to a reigning monarch since Queen Victoria's last, Princess Beatrice, in 1857.
An uncomplicated, boisterous child, it is said he is the Queen's favourite.
At Gordonstoun school in Scotland, he acquired a reputation as a young man who was certainly not lacking in self confidence. One contemporary described him as "a man with a big bottom who laughed at his own jokes".
He made his first solo flight as a glider pilot in 1976 and decided to follow his father and brother into the Royal Navy, choosing a 12-year short career commission, which he extended, as a helicopter pilot.
He received his wings from the Duke of Edinburgh in April 1981, as well as winning the award for best pilot, becoming a royal "top gun".
At 22, Andrew saw active service as a Sea King helicopter pilot in the Falklands War. His service included flying his helicopter as a decoy target, trying to divert deadly Exocet missiles away from British ships.
Many years later, following his divorce, he would headlines of a different kind - mainly for making the most of his bachelor status.
He was spotted cavorting with topless women on holiday in Thailand and attended a "hooker and pimps" party with Robert Maxwell's daughter Ghislaine Maxwell in the US.
After serving for 22 years in the Royal Navy, the duke became the UK's special representative for international trade and investment.
His 10-year stint in the role generated a great deal of controversy.
As a roving ambassador, one of his first tasks was a post-September 11 trip to New York, but Andrew was criticised for attending a party during his stay.
He was dubbed Air Miles Andy amid criticism of his globe-trotting. He was accused of over-using helicopters at taxpayers' expense, in particular to attend golf-related dinners as a member of the Royal and Ancient Golf Club of St Andrews.
The duke also faced questions over his connections to politicians in Azerbaijan, Kazakhstan, Tunisia, Libya and Turkmenistan.
His judgment was questioned after he held meetings with Libyan leader Col Muammar Gaddafi's son Saif, and when he entertained the son-in-law of Tunisia's ousted president Zine El Abidine Ben Ali at Buckingham Palace.
His relations with Timor Kulibayev, son-in-law of the president of Kazakhstan, were also scrutinised after Mr Kulibayev purchased the duke's Sunninghill Park home for £3 million more than its £12 million asking price in 2007.
In November 2010 a secret cable published on the whistle-blowing website WikiLeaks revealed a US ambassador wrote that the Duke of York spoke "cockily" during an official engagement, leading a discussion that "verged on the rude".
Tatiana Gfoeller, Washington's ambassador to Kyrgyzstan, also said Andrew criticised the Serious Fraud Office investigation of an arms deal between British Aerospace (BAe) and Saudi Arabia, and accused Guardian journalists of "poking their noses everywhere" for investigating the deal.
Following the Wikileaks revelations, Simon Wilson - Britain's deputy head of mission in Bahrain from 2001 to 2005 - wrote in the Daily Mail that the duke was "more commonly known among the British diplomatic community in the Gulf as HBH: His Buffoon Highness".
"This nickname stemmed from his childish obsession with doing exactly the opposite of what had been agreed in pre-visit meetings with his staff," Mr Wilson said.
There were also long-running complaints about the lavish nature of his official foreign trips.
In 2011, it emerged he was friends with American financier Jeffrey Epstein, who was sentenced to 18 months in prison in 2008 for soliciting a minor for prostitution.
Pictures surfaced of Andrew with his arm around Virginia Roberts, now Virginia Giuffre, who claimed Epstein employed her as a masseuse but exploited her while a teenage minor.
He was also shown walking in New York's Central Park with Epstein in December 2010, a year after Epstein's release from prison, and this led him to quit his role as a trade envoy.
In 2013, he was elected a royal fellow of the Royal Society, but Britain's pre-eminent scientific institution faced unprecedented dissent from members over the move, with one professor describing the duke as an "unsavoury character".
Tech-savvy Andrew, who was the first member of the royal family to have his own official Twitter account under his own name, focused on his Pitch@Palace work encouraging young entrepreneurs to embrace technology start-ups, launching a range of initiatives to inspire youth innovators.
Then in 2015, while enjoying a new year skiing holiday with his family, Andrew was named in US court documents as having had sex with a 17-year-old three times between 1999 and 2002 in London, New York and on Jeffrey Epstein's private Caribbean island when the girl was still a minor under US law.
She alleged she was "procured" for the duke by Epstein, whom she accused of using her as a "sex slave".
She was identified in reports as Virginia Giuffre - the girl with whom the duke had been pictured.
Andrew vehemently denied the allegation.
His ex-wife Sarah backed him and his daughters rallied round as he vowed to push ahead with his work.
In April 2015, a US federal judge ordered the claims to be struck from civil court records as the long running lawsuit against Epstein carried on.
But his association with Epstein hit the headlines once again in 2019, amid the continued investigations into Epstein, who killed himself in prison in August while awaiting trial on sex trafficking and conspiracy charges.
Andrew's so called "car crash" Newsnight appearance was intended to draw a line under the matter.
But the Epstein saga and the duke's conduct during the on-camera interview ultimately led to his downfall - and the end of his official duties as a royal.
