Prince Andrew is often referred to as Queen Elizabeth II's "favourite son" but his image as a playboy former war hero has been repeatedly hit by scandal.
In 1982, just 22 years old, he was hailed for piloting Royal Navy helicopters during Britain's last colonial war in the Falkland Islands, after Argentina troops invaded.
That now stands starkly at odds with Andrew's public defence of his friendship with US sex offender Jeffrey Epstein in a lengthy television interview broadcast last weekend.
The interview, in which he denied having sex with a 17-year-old girl allegedly trafficked by the disgraced financier, has been seen as a public relations disaster.
Andrew, who is eighth in line to the throne, was criticised for arrogance and lacking compassion for Epstein's victims, prompting businesses and charities to distance themselves from his projects.
On Wednesday, he was forced into a humiliating withdrawal from public engagements to avoid further damaging the royal brand and those associated with it.
Spare to the heir
Born Prince Andrew Albert Christian Edward on February 19, 1960, at Buckingham Palace, he was the third child of the queen and Prince Philip and the first to be born to a reigning monarch since Queen Victoria's daughter Beatrice in 1857.
His elder brother is heir to the throne Charles, Prince of Wales. The other brother Edward, Earl of Wessex, is four years his junior.
As a young man, Andrew was seen as one of the world's most eligible bachelors and was linked to a string of women before he married Sarah Ferguson in 1986.
The couple - who took the title the Duke and Duchess of York -- had two daughters, Beatrice, born in 1988, and Eugenie, who arrived two years later. But the marriage broke down.
After their separation in 1992, "Fergie" was photographed topless next to a swimming pool in the south of France cavorting with a US businessman.
The couple formally divorced in 1996 but have remained on good terms, with frequent speculation they could even remarry. The duchess reportedly still lives in the same Windsor home as her ex-husband.
Following their split, Andrew has been snapped sunbathing with topless women in Thailand and even at a so-called "hookers and pimps" party with the New York socialite Ghislaine Maxwell.
Maxwell, whose father was the media tycoon Robert Maxwell, has been accused of procuring underaged girls for Epstein. She has always denied the claims.
Andrew left the navy in 2001 and became a special government trade envoy, earning a new nickname -- "Airmiles Andy" - as he jetted around the world at taxpayers' expense.
Questions were also asked about his judgement after he was linked to the son-in-law of Tunisia's deposed ex-president Zine al-Abidine Ben Ali, Libyan dictator Moamer Khadafi's son Saif, and a Kazakh billionaire.
He has also faced repeated claims of being brash, arrogant and rude.
But his links to Epstein, who was found guilty in 2008 of paying young girls for massages but served just 13 months in jail under a secret plea deal, threatens to eclipse that.
Epstein was found dead in a New York jail in August after being arrested on federal sex trafficking charges.
The Epstein scandal resurfaced in 2011 when a photo emerged of the prince with his arm around Virginia Roberts, who was 17 at the time and has since claimed she was forced to have sex with him.
Andrew has repeatedly denied this and suggested the photo could have been doctored.
Another photo showed him walking with Epstein in New York's Central Park in December 2010, a year after he left prison.
The prince said in Saturday's interview he had "let the side down" by continuing his friendship with Epstein but said he was trying to act in an "honourable" way.
He refused to denounce Epstein completely, saying his home in New York had been a "convenient place to stay" and describing the financier's behaviour as "unbecoming".
Corrected by the interviewer that Epstein was a convicted sex offender, the royal said he was trying to be polite.
Since then it has been open season, as the media has dredged up his past and newly-found indiscretions, including claims he used racist language on more than one occasion.