Justin Bieber's Troubling Timeline: 25 Unfortunate Moments From The Past Year

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Justin Bieber appeared briefly in front of Judge Joseph Farina, via video, clad in red jail-issued scrubs at Miami-Dade Circuit Court in Florida, Ja. 23, 2014. Bond was set at $2,500.

From monkey quarantines to tour bus raids, here are the signs of trouble before Bieber's DUI arrest.

Make no mistake, Justin Bieber has enjoyed multiple professional achievements in the past year, including a record fifth No. 1 album on the Billboard 200 chart; an international tour that grossed $77 million in 2013, according to Billboard Boxscore; and a 'Music Mondays' series that featured some of the strongest songs of his young career. Yet all of these accomplishments occurred during a year riddled with personal missteps. From multiple in-show issues to run-ins with paparazzi to a handful of lawsuits to several accounts of reckless driving, Bieber's year has been wildly uneven, and hit a new low on Thursday (Jan. 23) when the 19-year-old pop superstar was arrested on suspicion of DUI and drag racing in Miami Beach, and subsequently failed a sobriety test.

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The arrest is Bieber's first, but not the first sign of trouble. Here is a list of 25 unfortunate events from the past year of Bieber's pored-over career:

Feb. 10, 2013: Bieber attempts to host a livestream video during GRAMMYs ceremony, but Ustream experiences capacity issues. "Never been so frustrating," he writes.

March 2, 2013: Bieber tells fans that he has the "Worst birthday" after his 19th birthday soiree in London is cut short, reportedly due to a disagreement with security.

March 5, 2013: Bieber issues a statement of apology after showing up late to a performance in London due to technical difficulties. "I never have any intent to upset or let anyone down," he writes.

March 6/7, 2013: One day after struggling to breathe mid-performance and fainting backstage, Bieber lashed out at a photographer in London with a stream of expletives. The verbal exchange was broadcast across Britain's media.

March 26, 2013: Allegations of battery are made after the singer is involved in a verbal altercation with a neighbor, who claims the pair came into physical contact. Bieber is not charged for the incident, which apparently stemmed from the neighbor complaining about Bieber's reckless driving.

March 30, 2013: Bieber is forced to leave his pet monkey in quarantine in Germany after failing to have the necessary documentation to bring the animal out of the Munich airport.

April 15, 2013: Bieber is widely criticized after visiting the Anne Frank House museum in Amsterdam and writing into a guestbook that the Holocaust victim "would have been a Belieber."

April 25, 2013: Bieber's tour bus is raided by police in Stockholm, Sweden, after an officer smelled marijuana coming from the vehicle. Unspecified narcotics are reportedly found on board, but no one is charged.

May 5, 2013: Bieber is tackled on stage by a crazed fan during a performance in Dubai.

May 7, 2013: A lawsuit is filed against Bieber and close friend Usher by two songwriters who claim the pair stole Bieber's hit "Somebody To Love" from them in 2009.

May 18, 2013: Bieber is booed onstage at the 2013 Billboard Music Awards while receiving the first-ever Milestone Award. "I'm an artist, and I should be taken seriously. All this other bull should not be spoken of," he tells the crowd.

May 28, 2013: Multiple onlookers, including former NFL star Keyshawn Johnson, publicly complain about Bieber's reckless driving in his hometown of Calabasas, California.

June 16, 2013: Bieber collides into a photographer with his Ferrari in Hollywood, and the incident is captured on video. No one is cited by police or injured during the incident.

June 25, 2013: A lawsuit is filed by a paparazzo who claims Bieber kicked and punched him at a shopping center in Southern California in 2012.

July 9, 2013: A video leaks showing Bieber urinating into a janitor's mop bucket and yelling "F--- Bill Clinton" as he passes a photo of the former U.S. president. Bieber later apologizes for the incident. 
July 28, 2013: U.S. border agents find marijuana on Bieber's tour bus as it crosses into Canada from Detroit. Bieber is not on the bus at the time of the bust.

October 7, 2013: A new photograph of Bieber holding what looks like a marijuana joint surfaces. Bieber was previously photographed holding what appeared to be a joint in January 2013.

October 10, 2013: Bieber is accused of physically attacking a DJ in South Korea over his music choices at a night club.

November 1, 2013: Bieber is reportedly photographed leaving a brothel in Rio de Janeiro, Brazil.

November 2, 2013: Bieber leaves a performance in Brazil early after being pelted with a bottle onstage. Fans hang around the show for a half-hour hoping he would return, to no avail.

November 6, 2013: Bieber is allegedly caught painting graffiti on a wall in Brazil, a crime punishable by up to one year in jail in the country. A similar charge is lobbed at Bieber during his tour visit to Australia.

November 13, 2013: Bieber apologizes to fans after inadvertently sweeping an Argentinian flag offstage with his foot and mic stand during a performance in Buenos Aires. "Im so sorry for anyone who took my actions the wrong way and I hope you can forgive this mistake," he writes on Twitter.

December 24, 2013: Bieber posts on Twitter that he is "officially retiring," and obliquely points out how the media makes up "a lot of lies" about him.

January 14, 2014: Bieber's California home is searched and the singer is questioned by the L.A. County Sheriff's department after Bieber allegedly egged a neighbor's house. An unspecified amount of cocaine was discovered in Bieber's home, and one of the singer's friends was arrested for felony drug possession.

January 23, 2014: Bieber is arrested after being pulled over for drag racing in Miami Beach, and fails a drug test after being taken into custody.