![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-503172518-1.jpg?resize=618%2C412&ssl=1)
Hollywood bad boy Chris Brown is no stranger to legal trouble. TheWrap looks back at some of his most outrageous moments and run-ins with law enforcement.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-500894024.jpg?resize=618%2C412&ssl=1)
February 8, 2009
Brown was 19 years old when he punched, choked and bit then-girlfriend Rihanna. Brown pleaded guilty to one count of felony assault.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/chris-brown-good-morning-america-robin-roberts.png?resize=618%2C412&ssl=1)
March 22, 2011
“Good Morning America” co-host Robin Roberts asked Brown repeated questions about Rihanna during his visit to the show, after which the artist stormed off set, and threw a chair through his dressing room window.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-579173348.jpg?resize=618%2C412&ssl=1)
June 14, 2012
Brown was injured after an altercation with Drake at a New York nightclub, where bottles were broken and punches were thrown over mutual ex-girlfriend Rihanna.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/chris-brown-valet.png?resize=618%2C412&ssl=1)
March 7, 2013
Brown got hostile with a valet outside a Los Angeles bowling alley, after the parking attendant requested the $10 charge to release the singer’s car.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-451217062.jpg?resize=618%2C412&ssl=1)
October 27, 2013
After punching a man outside the W Hotel in Washington D.C., Brown was arrested for felony assault. According to TMZ, Brown said, “I’m not down with that gay s—, I feel like boxing” before attacking the man.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-487647307.jpg?resize=615%2C412&ssl=1)
March 14, 2014
After the Washington, D.C. incident compelled Brown’s judge in the Rihanna case to extend his stay at a Malibu rehab facility, he was kicked out and taken into custody for making a threatening comment, failing to submit to a drug test, and touching a female also undergoing treatment, according to the L.A. Times.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-475335530.jpg?resize=618%2C412&ssl=1)
September 14, 2015
According to the Denver Post, a woman in Colorado filed a report for third-degree assault after she claimed she was forcibly thrown off Brown’s tour bus for not surrendering her cell phone, which she said was broken in the skirmish.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-518977998.jpg?resize=618%2C412&ssl=1)
May 10, 2016
Michael Guirguis, Brown’s former manager once tasked with ameliorating the singer’s image, filed a lawsuit accusing the performer of “brutally attacking” him, “punching him four times in the face and neck.”
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-503172498.jpg?resize=618%2C412&ssl=1)
June 2, 2016
After his performance at a Las Vegas nightclub, Brown was accused of punching a woman who attempted to snap a picture of him, leaving her with a swollen, red eye.
![](https://i0.wp.com/www.thewrap.com/wp-content/uploads/2016/08/GettyImages-531505712.jpg?resize=618%2C415&ssl=1)
August 30, 2016
Brown was arrested for assault with a deadly weapon after a woman called 911 earlier in the day claiming the singer pulled a gun on her, according to TMZ.
The arrest ended an hours-long standoff with police at Brown’s Tarzana, California, home, during which he posted a series of videos on Instagram, professing his innocence and decrying the police as “idiots.”