Exposing his crown jewels in a Las Vegas hotel suite is by no means the young prince’s first brush with controversy. Harry has always shown much more of a wild side than his reserved older brother William, the future king. Ten years ago, Harry, then just 17, was sent to rehab for a day after being caught smoking marijuana and drinking underage. He’s since got into scuffles with photographers outside nightclubs, been filmed directing a racial slur, albeit seemingly in jest, towards a member of his army platoon, and been photographed wearing a red swastika armband to a rather un-PC “colonials and natives” themed costume party. On the whole, however, it could be worse. We can be grateful he hasn’t fathered a brood of illegitimate children or created another constitutional crisis, like some of the other royals on this list.