Prince Andrew, who has stepped down from public life for the foreseeable future over his friendship with convicted paedophile Jeffrey Epstein, has led a controversial life for decades.
From an astonishing relationship with a soft porn actress, to sharing a luxury yacht with topless women, his reputation as a royal has often teetered on the brink.
Here, we take a look at some of the lows of a Duke who’s never been far from causing a crisis…
THE PRINCE AND THE PORN STAR: Actress Koo Stark in 1976 soft erotic film Emily
THE PRINCE AND THE PORN STAR: Prince Andrew at a party with Koo Stark in 1999
PAINTING THE PRESS: Andrew sprays reporters with a paint gun from the window of an abandoned house in Los Angeles in April 1984. The Queen later ‘read him the riot act’
THE CLOWN PRINCE: Andrew plays his Joker with host Stuart Hall during the It’s A Royal Knockout in June 1987. The event was later described as undignified
INVITATION TO EVIL: Epstein and Ghislaine Maxwell after Andrew invited them to a Sandringham shoot in 2000
PARTYING WITH THE SUPER-RICH: Prince Andrew again consorts with his billionaire pal Jeffrey Epstein (back right), this time in February 2000 at the Mar-a-Lago resort of Donald Trump and wife Melania. They are also pictured
BUST OF BUDDIES: Andrew looks goggle-eyed after getting an eyeful of supermodel Heidi Klum’s chest in November 2000
ALL HANDS ON DECK: The Prince holds hands with American supermodel Normandie White in Thailand in 2001
ALL HANDS ON DECK: sunbathing with a topless woman on a yacht on the same break in 2001
THAT INFAMOUS PICTURE: Andrew appears to hold Epstein victim Virginia Roberts, then 17, by the waist as the sex offender’s lover Ghislaine looks on in 2001
A FAMILY BALL: The Yorks dress up in their glad rags to mark Beatrice’s 18th in 2006
GIVING THE ROYAL WAVE: Andrew waves goodbye to a brunette he let out of the door of his friend Epstein’s New York home in December 2010
GIVING THE ROYAL WAVE: Andrew walking with disgraced financier Jeffrey Epstein in Central Park, New York, a day before he was pictured waving to a brunette from Epstein’s door
TRADE WITH TYRANTS: Andrew was forced to step down as UK trade envoy for his links with Azerbaijan’s despot President Ilham Aliyev, here in Baku in 2011
AIR-BRAINED SCHEME: ‘Airmiles Andy’ came in for more criticism in 2014 when he arrived in India for a tour of Mumbai’s slums on a private jet. He also stayed in a £10,000-a-night suite and had the use of a butler
