Singer Chris Brown has managed to intrigue -- and infuriate -- the public since he first burst onto the scene in 2005. Here's a timeline of his troubled history:
February 2009: Brown's legal troubles began when Los Angeles police responded to a 911 call that a woman was assaulted on a Hollywood street just after midnight on February 8. They found his girlfriend, Rihanna, then 20, with a badly bruised face. Brown, then 19, turned himself into police hours before he and Rihanna were to perform at the Grammys.
March 2009: Brown apologized a week after his arrest. "Words cannot begin to express how sorry and saddened I am over what transpired," he said. "I am seeking the counseling of my pastor, my mother and other loved ones and I am committed, with God's help, to emerging a better person." He was formally charged with felony counts of assault and making criminal threats that March 5.
June 2009: Brown agreed to plead guilty to a felony assault charge in the Rihanna beating at a June 22 hearing. The plea deal included five years' probation, 1,400 hours of "labor-oriented service" and a yearlong domestic-violence counseling program.
June 2009: The judge asked Rihanna to appear in court to hear details of the order requiring Brown to stay 50 yards away from her -- 10 yards if the two appeared at the same industry event together. Here she appears with her attorney, Donald Etra.
August 2009: On the day Brown was sentenced in the assault, a probation report revealed he and Rihanna were involved in at least two other incidents of domestic violence before the February 2009 attack. One in Europe in fall 2008 involved Rihanna slapping Brown during an argument, and Brown responded by shoving her into a wall, the report said.
July 2009: Chris Brown posted a video apology for the assault. "I have told Rihanna countless times, and I'm telling you today, that I'm truly, truly sorry in that I wasn't able to handle the situation both differently and better," he said.
September 2009: Brown and his mother appeared on CNN's "Larry King Live" in his first TV interview since his arrest. "I've said countless times how sorry I am to Rihanna, and I just accepted full responsibility," Brown said. "But it's just one of those things I wish I could have relived and just handled totally different."
February 2010: Brown earned a glowing probation report six months after he was sentenced to "labor-oriented service" for assaulting Rihanna. "It looks like you're doing really, really well," Judge Patricia Schnegg told Brown during a February 18 probation hearing. The police chief in Richmond, Virginia -- where Brown was allowed to complete his sentence -- reported the singer had worked 32 days of hard labor. Here Brown performs on NBC's "Today" show in July 2011.
Summer 2010: That June, Brown broke down in tears during his performance of "Man in the Mirror" at the BET Awards in Los Angeles. In August, he received another good probation report. "You're doing very well on probation," the judge told him on August 26. His next probation report in November 2010 was also positive. After another positive review in February 2011, the judge removed the "stay away" order that barred Brown from contact with Rihanna.
March 2011: Brown stormed off the set of ABC's "Good Morning America" on March 22 after Robin Roberts mentioned the assault on Rihanna. Show staff called security after hearing "loud noises coming from Brown's dressing room," according to ABC. The thick glass window in Brown's dressing room window had been smashed, ABC said. Brown apologized the next day, saying he was "disappointed in the way I acted."
February 2012: A woman filed a police complaint against Brown, accusing him of grabbing her iPhone after she used it to take a photo of the singer in a car on a Miami street on February 19. The complaint prompted a police investigation that could have threatened Brown's probation, but no charge was ever filed. That same month, his album "F.A.M.E." won a Grammy for best R&B album.
June 2012: A fight allegedly between Drake and Brown and their entourages broke out at a New York nightclub on June 14. Brown said he was a victim. The melee left Brown with a nasty gash on his chin and fueled rumors that it started because of an argument about Rihanna, whom both men have dated. Here Drake, left, and Brown hang out in New York in August 2010.
September 2012: Brown's streak of glowing probation reports came to an end on September 5 when the judge lectured him for testing positive for marijuana use in Virginia. The drug test failure did not result in a probation violation, although pot is illegal in Virginia. Brown told authorities he ingested the marijuana in California, where he has a medical marijuana card, according to the judge. Rihanna tweeted to Brown: "I'm praying for you and wishing u the best today!" Brown responded, "Thank u so much." Here Brown appears in court in September 2013.
January 2013: Los Angeles detectives investigated a brawl allegedly involving Brown and singer Frank Ocean, pictured, at a West Hollywood recording studio on January 27. Witnesses said Brown punched a man, a sheriff's statement said. No charges were filed, but the incident was included months later when a prosecutor sought to have Brown's probation revoked.
February 2013: Prosecutors accused Brown of falsifying his community labor reports and asked the judge to revoke the singer's probation. The prosecutor also brought up the fight with Frank Ocean, the Miami cell phone incident and Brown's "Good Morning America" tantrum. "Apparently the district attorney's office has completely lost their minds," Brown's attorney told reporters. Rihanna sat behind Brown at the February 5 hearing.
February 2013: Brown totaled his black Porsche while being "ruthlessly pursued by paparazzi" on February 9, his rep said. Brown told Beverly Hills police he backed the car into a wall while "he was being chased by paparazzi, causing him to lose control of his vehicle," a police statement said. No charges were filed.
June 2013: A woman accused Brown of assaulting her at an Anaheim, California, nightclub on June 22. Brown's rep told CNN the accusation was "totally false and unfounded." Anaheim police investigated, but no case was made against Brown.
July 2013: Brown's probation was revoked July 15 after he was accused of hit-and-run driving and driving without a license. A woman told investigators Brown "went ballistic" after a traffic accident and screamed at her. The charges were dropped after Brown reached a "civil compromise" with his accuser a month later. Here, he appears in court with his attorney, Mark Geragos.
August 2013: A deal to reinstate Brown's probation was reached, but it meant the singer had to complete an additional 1,000 hours of community labor in Los Angeles. The agreement allowed Brown to avoid a trial on the question of whether he had falsified his community labor reports in Virginia. Here, Brown's attorney, Mark Geragos, talks to reporters after a judge dropped a hit-and-run charge against Brown that same month. The singer reached a "civil compromise" with his accuser.
October 2013: Brown and a bodyguard were accused of assaulting a man on a Washington sidewalk on October 27. The man told police he tried to jump into a photo that Brown was posing for with a female fan when the singer said, "I'm not down with that gay s--t" and "I feel like boxing." Isaac Adams Parker said Brown punched him in the face, the police report said. Brown was released from jail the next day.
October 2013: Chris Brown reached into Lindsay Lohan's playbook for avoiding jail: Go to rehab before your court date. The singer's assault charge put him on a path toward possible jail time, but he entered a Malibu, California, rehab facility on October 29. "His goal is to gain focus and insight into his past and recent behavior, enabling him to continue the pursuit of his life and his career from a healthier vantage point," his rep said.
November 2013: A judge ordered Brown to enter another rehab program and stay for 90 days. A probation report revealed at a November 20 hearing that Brown was booted from a rehab facility for smashing his mother's car window during a family session. "There is much concern with the probationer's new arrest and his violent outburst that resulted in his discharge from a treatment facility," the probation report said, referring to Brown's assault arrest in Washington.
December 2013: Brown's new rehab doctors reported on December 16 they "witnessed very positive change in Mr. Brown since his psychotropic medications have been changed and he has been taken off medical marijuana." After nearly a month on the court-ordered program, they said Brown's "ability to emotionally regulate himself has improved markedly." The judge delayed a decision on if he would send Brown to jail after he completed his 90-day rehab visit.
January 2014: Brown appeared before a judge along with his bodyguard on January 8 for a hearing on the Washington assault charges. Brown rejected a plea deal, putting the case on a track toward a trial in April.
February 2014: A judge rejected the prosecutor's motion to pull Brown from rehab and send him to jail on February 3. Brown was becoming more violent, with his outbursts "increasing in severity and intensity," a deputy district attorney argued. Judge James Brandlin ruled Brown was again in violation of probation, but he cited a new probation report saying the singer was "doing well in the program and making great strides" in rehab.
February 2014: Brown successfully completed a 90-day, court-ordered rehab program in November, but the judge decided on February 28 that the singer should remain a resident in the facility until after his assault trial in April. Brown seemed disappointed by the decision, although his therapy may have helped him handle the stress. He closed his eyes and appeared to meditate, while his attorney met privately with the judge and prosecutor.
March 2014: Brown was jailed on March 14 after being booted from the Malibu, California, facility where he had been treated for four months. He was "cooperative when taken into custody," a sheriff's department statement said. A judge ordered him to stay in jail at a hearing three days later, revealing he was kicked out after counselors said he wrote a "provocative" statement and violated other rehab rules.
May 2014: Brown appears in court for a probation violation hearing on May 9. He admitted to violating his probation and was ordered by a judge to serve one year in jail.
- Chris Brown entered his guilty plea in a D.C. court Tuesday
- The plea deal includes no jail time or probation for Brown
- The singer has already paid a heavy price for the incident
- Brown's probation for beating singer Rihanna is set to end in January
(CNN) -- Chris Brown pleaded guilty to simple assault Tuesday to settle a case stemming from a sidewalk fight at a Washington hotel last October.
"I'm sorry, I am very sorry," Brown told the judge in the brief hearing in a District of Columbia court.
The judge sentenced Brown, 25, to time served -- the one day he was locked up after his arrest -- and no probation for the simple assault conviction. He must also pay a $150 fine.
The singer has already paid a heavy price for the incident -- it resulted in the revocation of his probation for the 2009 beating of ex-girlfriend Rihanna in Los Angeles. He spent five months in court-ordered rehab and another three months in jail because of it.
His jail time also included two grueling cross-country trips on the federal government's "Con Air" inmate transport system.
A doctor's letter included in a probation report said that Brown was diagnosed as bipolar, which is blamed for violent outbursts.
Doctor: Chris Brown makes 'strides' to sobriety, 'personal growth'
"Mr. Brown has made significant strides in maintaining his sobriety, as well as developing skills that promote personal growth," a psychiatrist wrote in the most recent report in August.
Read Brown's probation report (PDF)
He is taking his twice-a-week court-ordered psychological therapy sessions seriously, the doctor said.
"He continues to show great perseverance in implementing recommendations made by his treatment team, utilizing his learned skills and seeking guidance in his recovery process," his doctor reported.
Brown's probation officer said he has been "working on personal growth" and has been "taking responsibility for his behaviors" in the two months since he was freed from jail.
His probation for the 2009 felony battery conviction is expected to end on January 23, 2015, as long as he stays out of legal trouble and completes another 600 hours of community labor, the probation officer said last month.
The singer will spend three days each week until then working on a community labor crew.
Brown was a teenager when his remarkable dancing and singing talents made him a pop star. He was 19 when he smashed Rihanna's face with his fist during an argument inside a rented Lamborghini on the evening of the 2009 Grammy Awards.
With his legal troubles and probation requirements apparently nearing an end, Brown should have more time to concentrate on his career. He has a new album set to release this month, and he has teased fans with a Twitter post that suggested he would soon start a concert tour.
Rihanna gives painful details of Chris Brown assault
CNN's Lindy Royce contributed to this report.
