Britain's Prince Harry has been caught on camera doing something embarrassing - again. On Aug. 21, 2012, celebrity gossip website TMZ posted photos of the 27-year-old royal cavorting nude with an unidentified woman in a VIP suite in Las Vegas.

It's hardly the first time the prince - who allegedly disrobed as part of a game of strip pool - has been caught misbehaving. Take a look back at some of Harry's previous bad-boy behavior.

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In January 2009, the British tabloid News of the World released videos on its website shot by Prince Harry during his military service in 2006, in which he was heard referring to one of his fellow cadets as "our little Paki friend" and telling another that he looked like a "raghead."

A spokesman for St James' Palace said, "Prince Harry fully understands how offensive this term can be, and is extremely sorry for any offence his words might cause. However, on this occasion three years ago, Prince Harry used the term without any malice and as a nickname about a highly popular member of his platoon. There is no question that Prince Harry was in any way seeking to insult his friend."

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In January 2005, Prince Harry apologized after a tabloid newspaper printed a picture of him wearing a Nazi soldier's uniform to a costume party. The Sun showed Prince Harry (seen here in May of that year) clutching a cigarette and a drink and wearing a swastika armband.

Asked to comment on the photo, the prince issued a statement saying he is "very sorry if I caused any offense or embarrassment to anyone... It was a poor choice of costume and I apologize."

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In October 2004, Prince Harry was hit in the face with a camera during a scuffle with a photographer outside a London nightclub. Official royal word was that the prince then cut a photographer's lip when he pushed the camera away.

While the palace said Harry (seen in a September 2004 photo) acted in self defense, the photographer involved, Chris Uncle, said the prince "deliberately lashed out."

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In October 2004, a former teacher of Prince Harry's at Eton College claimed before a tribunal that she was unfairly dismissed from the school after being ordered to help the prince cheat on an exam in 2002 and claimed to have a tape to prove it.

Paddy Harverson, a spokesman for Prince Charles, told the hearing that the allegations had previously been disproved and it was unfair for the teacher's lawyers to give the court only a small portion of the tape. Harverson accused them of having "placed their own interpretation upon it."

"The tape ... contains barely audible half-sentences, and it appears to have been edited," Harverson said. "It is also difficult to tell what Harry is saying and what he is referring to, due to the poor quality of the recording and the disjointed nature of the tape. The fact remains Harry did not cheat."

The prince is seen at left in a July 2004 photo.

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In 2001, Harry, then 17, confessed to his father that he had smoked marijuana several times and got drunk at parties he held at his father's Highgrove country estate in western England.

Charles reprimanded Harry (seen at center in this photo from August 2001) and sent him to visit a drug rehabilitation clinic in south London to see for himself how drugs can ruin young people's lives. Queen Elizabeth II said that she was pleased with the way Prince Charles handled the problem.

"The queen shares the Prince of Wales's views on the seriousness of Prince Harry's behavior and supports the action which has been taken," Buckingham Palace said in a statement. "She hopes the matter can now be considered as closed."

Pictures: Prince Harry