Criticizing a Prince Tribute and More of Justin Bieber's Most Controversial Moments

Justin Bieber's Most Controversial Moments
Source: Justin Bieber/Instagram

04/22/2016 AT 02:05 PM EDT

Like all kids who grow up, Justin Bieber has made some mistakes along the way.

Unlike all kids, the world watched as Bieber blundered in front of millions of social media followers in endlessly shared videos and in oft-re-quoted interviews.

Below, some of the most memorable remarks that left fans waiting for the Biebs to say "Sorry."

The Prince shade
Guitarist Andrew Watt posted an emotional tribute to Prince after news broke of the music legend's death. "Today waking up to this news I am truly beside myself … devastated … the last of the greatest living performers … my guitar idol," the musician wrote on Instagram.

This past Tuesday night before my show I was picking out an outfit...I was so tired from the past week of endless traveling and gigging that I grabbed my Prince shirt and said fuck it I'm gonna channel the purple one tonight...I didn't shower after the gig out of pure exhaustion...I went to sleep in that shirt and then I wore it again all day waking up to this news I am truly beside myself...devastated...the last of the greatest living guitar idol...his connection to ALL his instruments yielded a sexual transcending aura and the world is just less fucking cool without him walking on it... "Electric word life It means forever and that's a mighty long time But I'm here to tell you There's something else... The after world" #RIPPRINCE

A photo posted by Andrew Watt (@andrew50watt) on

For reasons yet to be fathomed, Bieber decided to leave an oozing-with-shade comment on the post. "Well not the last greatest living performer," he wrote. Many pointed out that while yes, we can all probably concede that there are at least a couple great performers still gracing the earth, clearly the proper time to get technical about it is not immediately following the unexpected death of a beloved musical innovator. And, you know, especially when the person getting so uppity is an overgrown tween pop star.

The Anne Frank comments
A then-19-year-old Bieber visited Amsterdam's Anne Frank House in-between stops on the European leg of his 2013 tour. At the time, a source told PEOPLE that he made the trip after reading the famous diary Frank wrote while in hiding during the Holocaust. One would think bad PR couldn't possibly stem from a celebrity taking interest in one of the most poignant, tragic figures of the 20th century, but Bieber again found himself on the receiving end of vitriolic criticism.

"Truly inspiring to be able to come here. Anne was a great girl. Hopefully she would have been a belieber," he wrote in the museum's guestbook, according to their Facebook page.

A number of celebrities poked fun at Bieber for the message on Twitter.

The Japanese war criminal shrine incident
While visiting Japan in 2014, Bieber posted a picture of himself bowing in front of Yasukuni Shrine with the caption "Thank you for your blessings." Unbeknown to him, the highly controversial monument is said to enshrine the souls of some of the country's most brutal war criminals, including military leaders involved in the atrocities of World War II.

The pop star complied when Chinese fans began flooding Twitter and Instagram with requests that he remove the offending photo. "While in Japan I asked my driver to pull over for which I saw a beautiful shrine. I was mislead to think the Shrines were only a place of prayer," he explained on Instagram. "To anyone I have offended I am extremely sorry. I love you China and I love you Japan."

His comments on abortion
Rolling Stone asked a 16-year-old Bieber for his thoughts on some political and social issues, and as you would probably expect from any teenager, his comments were not entirely well-considered.

"I really don't believe in abortion," Bieber said. "It's like killing a baby." When it comes to cases of rape, he added, "Um. Well, I think that's really sad, but everything happens for a reason. I don't know how that would be a reason. I guess I haven't been in that position, so I wouldn't be able to judge that."

The n-word videos
The year 2014 brought some struggles for Bieber as videos of his 14 and 15-year-old selves making jokes that involved the n-word surfaced.

The first footage to emerge, which was published by TMZ, showed the teen telling a joke that begins "Why are black people afraid of chainsaws?" and ends with a string of the racial slur.

Bieber issued an apology to the Associated Press when the years-old video came to light. "I'm very sorry," he said. "I take all my friendships with people of all cultures very seriously and I apologize for offending or hurting anyone with my childish and inexcusable behavior."

"I thought it was ok to repeat hurtful words and jokes, but I didn't realize at the time that it wasn't funny and that in fact my actions were continuing the ignorance," the statement continued. "Thanks to friends and family I learned from my mistakes and grew up and apologized for those wrongs. Now that these mistakes from the past have become public I need to apologize again to all of those who I have offended … Ignorance has no place in our society and I hope the sharing of my faults can prevent others from making the same mistake in the future. I thought long and hard about what I wanted to say but telling the truth is always what's right. Once again ... I'm sorry."

Unfortunately for him, another slur-filled video of Bieber emerged within the week. In the clip, the teen star parodies his hit "One Less Lonely Girl." "One less lonely n-----," he sings through a smile. "If I kill you, I'd be part of the KKK, and there's gonna be one less lonely n-----."

Bieber issued his second apology in an interview with The Sun. "Facing my mistakes from years ago has been one of the hardest things I've ever dealt with," he said. "But I feel now that I need to take responsibility for those mistakes and not let them linger. I just hope that the next 14-year-old kid who doesn't understand the power of these words does not make the same mistakes I made years ago. At the end of the day I just need to step up and own what I did."
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