2014: Chris Brown is taken to jail for violating his probation while in rehab.

At this point in his career, Chris Brown was getting into various issues with the law, even while he was on probation for his 2009 assault on his former girlfriend Rihanna. In October 2013, Brown was charged for allegedly punching a man and breaking his nose in Washington, D.C. He was arrested for felony assault, but got the charge down to a misdemeanor and entered rehab on his own before he was sentenced.

Fast forward two weeks; Brown gets kicked out of the rehab facility for general misbehavior. He also threw a rock through his mother's window right before he was discharged from rehab in November; this gets him a new 90 day sentence at a Malibu, Calif. rehab facility to work on his anger management issues.

During that 90 day stint, he broke the institution's rules by touching a woman in the treatment center, refusing to take drug tests and more. These issues violated his probation and he was taken into custody without bail.

On May 12, 2014, after sitting in custody for 2 months for his probation violation at the Malibu facility, he admitted that he punched the man in D.C. He gets sentenced to 365 days in jail for the confession, but ends up serving 108 of those days and is freed on June 2, 2014. With his newfound freedom, he pledged to change his outlook and stay out of trouble.

See 50 of the Most Clever Hip-Hop Lyrics

More From XXL