Over two billion people from around the world watched in awe as (arguably) the world’s most famous prince married his beautiful bride, former Suits actress, Meghan Markle.

Watch highlights from of the special day below:

But as traditional and pure as the royal wedding appeared, we all know that in his younger days, the Duke of Sussex’s reputation was a far cry from what it is now. From excessive drinking to racial slurs, the prince truly was a bad boy back in the day.

So, without further ado, here are 11 times Prince Harry embarrassed the Royal Family.

1. Kissing a soldier

Royals are supposed to be quiet about their dating lives and they’re certainly not supposed to engage in over-the-top PDA. However, back in 2009, photos of Prince Harry not only kissing but licking a soldier on his cheek were leaked to the internet.

While the photo caused minor outrage in upper-class circles, many gay activists were thrilled by the sight of a straight man comfortable enough in his sexuality to kiss a man.

“Kissing a fellow soldier in public is a very liberal and clear gesture for somebody who is heterosexual,” one activist remarked. “The world would be a much nicer place if all heterosexuals were like that.”

2. Smoking weed

Prince Harry was only 17 when he started smoking weed and when his father, Prince Charles, found out he sent him straight to rehab for some days. “This was a serious matter which was resolved within the family and is now in the past and closed,” royal officials told The New York Times.

3. Raunchy photos

Remeber back in 2012, when TMZ leaked some undeniably suggestive photos of Duke of Sussex living it up in Las Vegas? One of the photos showed the prince in the middle of a game of strip billiards in a Las Vegas hotel suite. He was entirely naked in the photo, his manhood covered by his hands. Buckingham Palace confirmed the authenticity of the photo which also featured an entirely naked female. “Prince Harry has been on a private holiday before he resumes his military duties,” a royal official told CNN.