“The Comedy Central Roast of Justin Bieber” gives comedians plenty of material to work with, since the singer has been making headlines for the wrong reasons for a long time now. After getting discovered in 2007, Bieber has been involved in plenty of scandals, but he was still declared one of the most powerful celebrities in the world by Forbes magazine three times in a row, in 2011, 2012 and 2013.

Check out some of Justin Bieber’s most controversial moments, that didn’t stop him from getting over 40 million followers on Twitter.

The Calvin Klein Ads

While Justin Bieber’s ads for Calvin Klein didn’t prove as iconic as Mark Wahlberg’s, they were also surrounded by a Photoshop controversy. The campaign was parodied on SNL and many have claimed that Bieber’s bulge had been arficially enhanced. 

Justin Beiber Calvin Klein Ads

The singer replied to the accusations like he always does, with a shirtless pic, wearing just a towel, with the caption “Photoshop lol.”

The Fashion Rocks Controversy

Justin Bieber Fashion Rocks Event

Justin Bieber proved himself to be a fan of the underwear even before he signed as the new face of Calvin Klein underwear. In September 2014, he stripped down to his briefs at the Fashion Rocks event. It ended up as one of Justin Bieber’s most controversial moments, since he mostly got boos from the crowd.

The Racist Joke

The internet was outraged when an old recording of Justin Bieber emerged, showing the singer making a racist joke. Plenty came to his defense, and Justin did apologize, explaining that “As a kid, I didn’t understand the power of certain words and how they can hurt. I thought it was okay to repeat hurtful words and jokes, but didn’t realize at the time that it wasn’t funny and that in fact my actions were continuing the ignorance."

The Orlando Bloom Bar Brawl

Justin Bieber Orlando Bloom Brawl

One of Justin Bieber’s most controversial moments involved an attempt from actor Orlando Bloom to punch him in Ibiza. Justin’s bodyguards protected the singer, who had apparently escalated the conflict. After making a derogatory comment about Miranda Kerr, Orlando’s ex wife, Justin continued to antagonize the actor, screaming “What’s up b****?” while his bodyguards protected him.

Egging a Neighbor’s House

Justin Bieber Egging Neighbor

One of Justin’s many run-ins with the law involved throwing eggs at his neighbor’s house in Beverly Hills. Even though he initially denied it, video evidence proved the case, and Justin was charged with vandalism, had to pay $80,900 in damages, and ended up on probation for two years.

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The Drag Racing Arrest and Deposition

Justin Bieber Drag Racing Arrest And Deposition

Getting his first mug shot was definitely one of Justin Bieber’s most controversial moments, when he got arrested for drag racing in January 2014, but he continued trying to top himself. Just two months later he was involved in a new scandal, when video of his deposition for a different case hit the web.

The Graffiti Scandal

Justin Bieber Graffiti Scandal

Justin Bieber’s destructive behavior wasn’t just limited to his stay in the US. The singer also caused problem in Rio de Janeiro, Brazil, when he was charged with vandalism. After he got permission to graffiti a site at the Olympic Village, Bieber was photographed by paparazzi at other locations as well, leaving his tag behind.

The Peeing Incident

Definitely one of Justin Bieber’s most controversial moments, the video of him peeing in a bucket in an NYC restaurant kitchen shocked plenty of his fans. After relieving himself in the mop bucket, Bieber also sprayed a photo of Bill Clinton with cleaning liquid and ending his tantrum with a “F*** Bill Clinton!”. He later apologized to the former president.

The Monkey Scandal

Justin Bieber Animal Cruelty

Continuing his tour of trying to break the law in as many countries as possible, Justin Bieber tried to take a capuchin monkey out of Germany without permission. The money was seized at customs.

The Anne Frank Comments

Justin Bieber Anne Frank Comments

One of Justin Bieber’s most controversial moments involved Anne Frank, one of the most famous victims of the Holocaust. After visiting her house in Amsterdam, the singer sparked outrage by leaving an inappropriate message in the guest book: “Truly inspiring to be able to come here. Anne was a great girl. Hopefully she would have been a belieber.”