Chris Brown's Highs & Lows: Top 10 Career Moments

Peggy Sirota
Chris Brown photographed by Peggy Sirota on August 26, 2014 at Quixote Studios in West Hollywood, California. Styling by EJ King.

Since his self-titled debut album almost 10 years ago, Chris Brown has crested mountains, but he's also dipped into the deepest valleys. The last year has been tough for the 25-year old, culminating in a jail stint earlier this summer. However, the talented singer-songwriter never stays down for long — even the prison guards were playing his latest hit, "Loyal."

Chris Brown on Life in Jail, Rihanna & More in Billboard Cover Story

Plus, his sixth studio album, X, was released Tuesday, Sept. 16. Early sales projections put X at 130,000 for its first week, and Brown currently has two singles, "Loyal" and "New Flame" in heavy radio rotation. Still, Chris Brown's career is the epitome of a checkered past. Here are the top 10 moments of Chris Brown's career, in chronological order.

1. Nov. 2005: Chris Brown's Debut Single "Run It!" Nabs No. 1
When Chris Brown appeared on the dance floor almost a decade ago, he quickly became Usher's most worthy competitor for the King of R&B crown. His debut single and video for "Run It!" proved not only did he have the voice to win the title, but he also had MJ's moves. Sure, he was a baby-faced teenager in a baggy jersey, but the Juelz Santana feature and bad-boy lyrics ("I can definitely show you things to have you sayin' I can't be 16") captured the ears and eyes of more than just the teenybopper crowd. Five months after its release in late June, the Scott Storch-produced R&B banger became Brown's first No. 1 on the Billboard Hot 100.

2. Sept. 2007: Chris Brown's First MTV VMA Performance
Chris Brown is a consummate performer, one of the best dancers since Michael Jackson first moonwalked. Never was this more apparent than in his explosive, aerobic 2007 VMA performance debut. Outfitted in a three-piece suit, Breezy leapt from stage to stage, slid across the floor like he was on roller-skates, flawlessly executed a mini MJ tribute and even let Rihanna share a little of the spotlight. It was a blistering performance that set the kind of bar that is referenced when any budding R&B star takes the stage.

3. Feb. 2009: Chris Brown Assaults Rihanna
Early in the morning before the 2009 Grammy Awards, Brown and then-girlfriend Rihanna were involved in a physically violent fight in Los Angeles. Rihanna was hospitalized with visible wounds on her face. Though Brown was scheduled to appear at the Grammys that night, he turned himself in to the LAPD. A month later, he was charged with felony assault and making criminal threats. After pleading guilty to a felony, he was sentenced to community labor, probation and domestic violence counseling in lieu of jail time. Public backlash from the assault was swift and remains strong.

4. Dec. 2009: Graffiti Is Critically Panned and Is Brown's Lowest Selling Album
Though Brown's third studio album generated several successful singles—including "I Can Transform Ya," featuring Lil Wayne—and was nominated for two Grammys, it was poorly reviewed and its sales were disappointing. Brown took to Twitter to chastise various stores for not stocking the album, claiming they were "blackballing" him. In its first week, Graffiti only sold just over 102,000 copies, compared to almost 300,000 for his previous album, 2007's Exclusive.

5. June 2010: Chris Brown's Riveting Performance at the BET Awards
At the 2010 BET Awards, Chris Brown stunned the audience with an incredible, show-stopping tribute to Michael Jackson. From the moment he appeared in silhouette to his thrilling moonwalk, he was MJ reincarnated, but it was the last two minutes of the performance that were the most crushing. Brown attempted to sing "Man in the Mirror," yet he was so choked up he couldn't get the words out. At the climax of the song, he was wracked with sobs and on his knees. The year before, Brown had issued a public apology for his assault of Rihanna, but this deeply moving breakdown was far more heartfelt.

6. March 2011: Following Good Morning America Interview, Brown Blows Up
After Graffiti's weak showing, Chris Brown seemed poised to make a comeback with F.A.M.E., his fourth studio album. The week of its release, he appeared on Good Morning America to perform and talk about the record. During the interview, co-anchor Robin Roberts began asking Brown about Rihanna having recently dropped her restraining order against him. He deflected the question, but Roberts persisted. Back in his dressing room, he allegedly smashed a window with a chair. He emerged shirtless and left before his second scheduled performance. Though he deleted it shortly after, he tweeted, "I'm so over people bringing this past shit up!!!" The next day on BET, he apologized, saying he was "disappointed in the way I acted."

7. March 2011: F.A.M.E. Becomes Chris Brown's First No. 1 Album, Earns First Grammy
Despite the GMA kerfuffle, Brown scored a massive success with F.A.M.E. Moving 270,000 units in its first week according to Nielsen SoundScan, the album debuted at No. 1 on the Billboard 200, giving Brown his first No. 1 album in the U.S. Six of the album's songs were popular singles, with the Busta Rhymes and Lil Wayne-assisted, Diplo-produced "Look at Me Now" quickly becoming a rap radio staple. Steeped in Eurohouse, "Beautiful People" positively shimmers.

Though he had been nominated for years, Brown had not managed to take home a gold statue. By the 2012 Grammys, he had already scooped up an armful of awards, including five BET Awards and Album of the Year at the Soul Train Awards. Capping a trying and tiring year (he supported F.A.M.E. with a choreography-heavy, optimistic tour), he not only finally won a Grammy for Best R&B Album, but he also performed on the show for the first time since his assault charge.

8. June 2012: Drake and Chris Brown Brawl at a NYC Club
Wars are fought over women, and Rihanna is quite a woman. No wonder Drake and Chris Brown allegedly brawled over her in a club in New York. After the incident, which left the VIP section littered with broken bottles, mirrors and tables, Brown Instagrammed a photo of himself with a gash on his chin. The guys traded barbs on wax, but the two apparently made up—they made light of their beef with a jokey ESPYs skit this July.

9. Oct. 2013: Chris Brown Is Arrested for Felony Assault, Enters Rehab
Last fall, Brown found himself in trouble again when he was arrested for felony assault in Washington, D.C. The fight allegedly began after two women asked for a photo with Brown and two men tried to get in the picture as well. One of the men wound up with a broken nose, and police reports state it was Brown, not his bodyguard, who threw the punch. The charge was reduced to a misdemeanor, and three days later, Brown voluntarily entered rehab. In mid-November, he was kicked out of the program and shortly thereafter, was sentenced to 90 days in an anger management facility. According to the New York Times, he then was expelled following both his refusal to be drug tested and his statements about guns and knives that other residents found disturbing. He also violated an agreement to stay two feet from females in the program.  

10. March 2014: Chris Brown Serves Time in Jail
Blowback from the D.C. incident was harsh. A judge decided the expulsion from the anger management rehab violated his probation for the 2009 assault on Rihanna. In a May court appearance, he sentenced Brown to 365 days in jail. However, Brown was given credit for serving 234 days due to rehab and jail time, which left 131 days. He served 108 before being released. There is a silver lining. While incarcerated, his smash hit "Loyal" reached No. 1. He heard the song plenty, too—prison guards played the song when he had visitors.

Since being released from jail, Brown seems to be doing what he does best, bouncing back. In interviews, he's been open and honest about how humbling doing time was and how helpful therapy has been. And this weekend, he's playing in a celebrity basketball game to benefit an anti-gang nonprofit. It looks like there will be more highs, than lows, to come for Chris Brown.