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London - Prince Harry has worked hard to transform his image from playboy to a modern royal serving Britain on the front line, but having naked pictures beamed around the world will not help his cause.
Harry spent a few wild days in Las Vegas and indulged in a spot of strip billiards, but in an age of camera phones his antics were soon fed to TMZ.
While British papers initially honoured the palace's pleas not to publish the photographs, the top-selling Sun tabloid broke ranks on Friday and splashed the images of the prince with nude mystery women across four pages.
The palace said that Harry, a trained army pilot of the deadly Apache helicopters, was simply letting off steam.
But his behaviour has raised questions about his maturity and about his security, at least one of the revellers snapped frolicking with him in a hotel swimming pool was reportedly one of his protection officers.
Harry has had difficult path to tread
Harry, the second son of Prince Charles and the late Princess Diana, has always had a difficult path to tread.
Though his elder brother William is on course to become king, Harry's every move is scrutinised nonetheless - and he has done his growing up very much in public.
When he was 17 he admitted having smoked cannabis, and he was soon a regular fixture at plush London nightclubs with booze, cigarettes, aristocratic beauties and a scuffle outside with paparazzi the common tale.
His mischievous antics were widely viewed with amused affection until he sparked a scandal in 2005 by attending a fancy dress party wearing a mock Nazi uniform.
That threatened to block his entry into the army, but he knuckled down and served as a front-line officer in Afghanistan for 10 weeks, until a media blackout broke down in 2008 and he was hastily withdrawn.
The following year his reputation took another knock when a video he made in 2006 emerged, showing him using the derogatory term "Paki".
'He is a prince with responsibilities'
Since then, the prince has immersed himself in military and charity work, gradually improving his profile.
He won plaudits for a mature performance mixed with fun as he made a diamond jubilee tour of the Caribbean on behalf of his grandmother Queen Elizabeth II this year, even beating the world's fastest man Usain Bolt in a mock race.
Robert Jobson, a royal correspondent and the author of Harry's War: The True Story of the Soldier Prince, said it was time Harry took a few lessons in maturity from William.
"I know he is young, free and single. But he is a prince with responsibilities," Jobson wrote in the Evening Standard newspaper on Thursday.
"He is bright enough and should have learned from his mistakes. The shame is that he had turned the corner. He represented his grandmother admirably at the Olympics closing ceremony and on a tour to Jamaica.
"But now it is time for him to wise up and follow Prince William's example."
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