Prince Harry can’t seem to stay out of trouble. The third-in-line for the throne had done an admirable job in the past year rehabbing his image from royal playboy to respectable—if a bit roguish—younger brother of Prince William. But embarrassing photos of Harry stark naked leaked to TMZ after a game of strip billiards while partying in Las Vegas swiftly thwart all of that progress. The behavior is less akin to the prince who confidently represented the Monarch at the Olympics, and more in line with the party boy whose reputation caused an Arizona mayor to caution him not to be caught “fornicating the night away and drinking into the small hours” while in the town of Gila Bend for Apache helicopter-training a year ago. The incident certainly isn’t the first time that Prince William’s younger brother has been the subject of scandal. From his brief stint in rehab to a wildly inappropriate Halloween costume, see photos of Harry behaving badly. Prince Harry’s bad-boy reputation can be traced back to his teenage years, when tabloids erupted with the news that that the 16-year-old been caught drinking and smoking marijuana on several occasions. It all happened during a two-month period in the summer of 2001, when Harry had the family’s Highgrove estate to himself. Prince Charles was none too pleased that his youngest son had made headlines for gallivanting around town, drinking with friends at local pubs, and smoking pot in their back yard, and promptly sent him to rehab after the news exploded. With regard to the cannabis, St. James Palace confirmed Harry had “experimented with the drug on several occasions,” but that his use couldn’t be described as “regular.” Toby Melville, Pool / AP Photo Two years after his brief stint in rehab, Prince Harry found himself in hot water again, when a former teacher at Eton College claimed school authorities had forced her to help the young royal cheat. Sarah Forsyth, 30, claimed she did nearly all the work on an art project that Harry submitted to pass an exam in 2002 that gained him entry into Sandhurst military-training academy—and she had the tape recordings to prove it. Her attorney quoted Harry as boasting about slacking on the project: “It was a tiny, tiny bit. I did about a sentence of it.” Prince Charles’s spokesman said the quotes were taken out of context, and that “the tape … contains barely audible half sentences and appears to have been edited. The fact remains Harry did not cheat.” Lefteris Pitarakis / AP Photo It was only a Halloween costume, but one would think the third in line to the British throne might have gone for something slightly less incendiary. In 2005 the 20-year-old prince was photographed at a party dressed as a German soldier and sporting a swastika on his arm. Later that week the picture appeared on the front page of The Sun with the headline, “Harry the Nazi.” Prince Charles’s communications team immediately issued a public apology on Harry’s behalf: “I am very sorry if I have caused any offense or embarrassment to anyone. It was a poor choice of costume and I apologize.” It was another instance of the prince making a poor judgment call, and the statement did nothing to quell fierce criticism. Politicians even piped in and called on Harry (who was officially an adult at this point) to apologize to the public himself, while a former armed-forces minister said Harry wasn’t “suitable” for Sandhurst, where he was scheduled to begin an officer training course later that year, and that were it not for his blood “the application wouldn’t be considered. Adam Butler / AP Photo At age 20, Harry was accused of “lashing out” and starting a fight with a photographer outside a London nightclub, Pangaea. A spokesman for the prince said he was just defending himself at the time. But the photographer insisted Harry “burst out of the car and lunged towards me as I was still taking pictures … The base of the camera struck me and cut my bottom lip.” Two years later, the prince got into a similar fight outside another London club. This time he chased down a photographer but fell to the ground before going back to his car. This photographer seemed less concerned, saying of the incident: “He obviously doesn’t like the paparazzi. If he wasn’t drunk, he’d have kept his balance, but because he’d been drinking he’s lost his balance, he’s gone down. It was one of those things—he came out of the club, they got entangled, and he lost his footing. The guy’s on a night out, he’s going to war, good luck to him I’d say.” Carl de Souza, AFP / Getty Images In 2009, Harry came under fire following the release of a 3-year-old video in which he is seen referring to a Pakistani cadet at Sandhurst as “our little Paki friend.” Later in the video, he called an officer-in-training “a rag head.” Harry quickly issued a statement saying he “used the term as a nickname about a highly popular member of his platoon.” But the following month, comments he made to a black comedian got him more bad press. Harry allegedly told Stephen K. Amos, who was appearing at Prince Charles’s birthday party, that he didn’t “sound like a black chap.” Amos later recalled, “I wanted to say, ‘How is I supposed to sound?’” Dylan Martinez, Pool / AP Photo Prince Harry’s reputation for being a booze hound escalated when reports surfaced that he was captured on video snorting a capful of vodka. The Sun claimed it obtained footage of the 23-year-old prince swigging from the bottle, spitting it out into a bottle top, and subsequently inhaling the regurgitated shot through one nostril as friends cheered him on. His spokesman refused to comment on the scenario, saying only that it was “a private matter.” Staying mum on the subject was likely a good move, since little could have been said to make Harry look like less of a royal fool. It’s an embarrassing day for the royal family when a spokesperson is forced to verify that, yes, that is a naked prince in that photo. Leaked pictures of Prince Harry fully nude during a recent bender in Las Vegas sent the press into a jaw-dropped tizzy—and royal aides into damage-control mode. The grainy photos, reportedly taken during a game of strip billiards in a $450-a-night Vegas suite, were apparently snapped by one of the “random girls” Harry had invited up to his room after a night of partying. In one photo, he stands full monty, but for bashfully covering his crown jewels with his hands. In another, he’s seen from behind—bum exposed—bear-hugging a girl. TMZ.com / Splash News