He's said to be the Queen's favourite son, but Prince Andrew is no stranger to controversy.
He was dubbed the "party prince" in the '80s as he wined and dined a string of models and actors and later "Air Miles Andy" as he jetsetted across the world in style.
Now the British tabloids have crowned him the "Pariah Prince" as charities and businesses abandon the royal over his ties to convicted sex offender Jeffrey Epstein.
• Prince Andrew's decades of unpleasantness revealed
• The royal treatment: Six words that sealed Prince Andrew's fate
• Isolated Prince Andrew's one remaining ally: his ex-wife
• Ugly truth about the royals and that trainwreck interview with Prince Andrew
As the Queen's second son is forced to step out of the public spotlight, here's how Prince Andrew earned his maverick reputation.
The 'Party Prince'
Andrew's life has always been privileged. He was born in Buckingham Palace, the first child born to a reigning monarch in more than a century.
His mother, 93, whose reign is the longest in British history, has been Queen his entire life.
As a young man in the early 1980s, he was often photographed squiring models and actors to fancy events, earning him the nickname "Randy Andy" or the "Playboy Prince", as he clearly enjoyed his role as one of the world's most eligible bachelors.
He briefly dated Koo Stark, an American actor who had appeared in several racy movies.
Their trip to the exclusive Caribbean island of Mustique drew worldwide attention, but the romance ended the next year.
The "uncomplicated boisterous" Andrew is said to be the Queen's favourite son.
Prince Charles has reportedly described him as "like a fizzy drink that has been shaken up and the top taken off".
Andrew joined the Royal Navy and served as a helicopter pilot in the Falklands War where his role was to fly a helicopter as a decoy target to divert missiles away from British ships.
Later, the Prince embraced domestic life and married Sarah Ferguson in 1986 in an elaborate ceremony at Westminster Abbey.
They had two girls – Princess Beatrice and Princess Eugenie – but the marriage ultimately ended in divorce.
In his interview with BBC Newsnight on Saturday, the Duke said he didn't drink, and he'd never understood why he earned the nickname of the "Party Prince".
"I don't know why I've collected that title because I don't … I never have really partied," he said.
"I was single for quite a long time in the early '80s, but then after I got married, I was very happy and I've never really felt the need to go and party."
'Air Miles Andy'
Prince Andrew was born without the responsibilities of his older brother, Prince Charles, the heir to the throne.
Instead, following his military career, he carved out a comfortable role for himself as a trade envoy and charity patron who could travel the world in style.
But he was forced to step down from the unpaid position as an international trade representative for Britain in 2011, in part because of his relationship with Epstein but also because of other questionable associations and complaints about his lavish travel arrangements.
He was heavily criticised in the media for his frequent use of helicopters to attend golf events.
Royal with a temper
The British public was not impressed by Prince Andrew's seemingly arrogant conduct during his interview on BBC Newsnight.
At one point the royal described himself as "too honourable" and said he regretted that Epstein had "conducted himself in a manner unbecoming".
"Unbecoming? He was a sex offender," journalist Emily Maitlis said.
"Yeah, I'm sorry. I'm being polite. I mean in the sense that he was a sex offender," he replied.
He also never once mentioned the underage girls Epstein had trafficked and sexually exploited.
It's not the first time Prince Andrew has been accused of being out of touch.
There have been multiple reports of meltdowns and foul-mouthed rages from disgruntled staff and former aides in the past.
A US ambassador also complained about the Prince's rudeness in a secret cable published by Wikileaks in 2010, where it was alleged the Duke of York spoke "cockily" during an official engagement, leading a discussion that "verged on the rude".
Simon Wilson – Britain's deputy head of mission in Bahrain from 2001 to 2005 – also told the Daily Mail the Duke was "more commonly known among the British diplomatic community in the Gulf as HBH: His Buffoon Highness".
Following his Newsnight interview, London tech founder and Downing Street aide Rohan Silva also alleged Prince Andrew used a racial slur involving the N-word during a meeting. Buckingham Palace has denied the claims.
Forced to step down
Prince Andrew's friendship with Epstein would prove to be the relationship that eventually brought down the Prince, forcing his retirement from public life.
In 2015, Prince Andrew was named in US court documents as having sex with 17-year-old Virginia Roberts, now Giuffre, three times between 1999 and 2002. Prince Andrew has vehemently denied the allegations, and they were struck from the record.
However, questions over his continued friendship with the sex offender after he was convicted have plagued Prince Andrew, leading to the disastrous Newsnight interview that he saw as a chance to draw a line under the long-running saga.
Instead, he was branded out of touch and unsympathetic following claims he was "too honourable" to break off a friendship with a sex offender.
On Wednesday, the final straw came when he announced he would step down from public life.