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Chris Brown’s in trouble again? Given his recent history, that’s hardly a surprise. In his latest encounter, after partying into the wee hours in a D.C. nightclub, Brown allegedly got into a confrontation with two young men who wanted to take a picture. Accused of throwing both gay slurs and ‘bows that broke one man’s nose, Brown was arrested for felony assault. Despite spending part of his weekend in jail, he was ultimately arraigned and released with the felony assault charge knocked down to felony misdemeanor for him and his bodyguard.

Though the incident sounds like it began as the kind of petty aggravation that celebrities deal with all the time, Brown’s participation once again landed him in tabloid headlines. His arraignment was a media circus, especially when singer Trey Songz showed up in support. Conflicting stories from witnesses, the victims and police led to the downgrade of charges but the kind of energy that surrounds Chris Brown these days reminds me of someone else. In the 90’s, Tupac Shakur was at the height of his fame. But a series of incidents – everything from a rape charge to an armed confrontation with undercover police to his shooting/robbery at Quad Studios in 1994, led to his becoming more known for his exploits in the streets than famous for his recordings.

After his still unsolved murder in Las Vegas in 1996, Shakur became one of rap’s enduring icons, a particular hero for the young and rebellious. While his music doesn’t have the social consciousness of Shakur’s, Brown, 24, is quickly becoming infamous in the Shakur model. Brown is a Grammy winner once considered a successor to Michael Jackson who has released 6 albums in 8 years – 2 platinum, 2 silver and one gold (numbers on his last, “X,” haven’t been released yet). His image, once that of a clean-cut star, has become more about his latest arrest/fight or Twitter rant than his music. (Shakur, it should be noted, did not have social media to express himself with.)

The first beginnings of tarnish to Brown’s image was, of course, his 2009 assault of then-girlfriend Rihanna, which polarized his fans. Some blamed her for the abuse; others found his behavior unforgivable. Although the couple reunited (and have since broken up) Brown’s public profile was significantly damaged. Subsequent incidents haven’t helped – he smashed his dressing room window with a chair during a meltdown at “Good Morning America” in 2011. He was upset by Robin Roberts’ questions about the Rihanna incident. Brown’s ongoing Twitter rants, including a vile response to a female comic who’d been taunting him via his feed, have left people questioning the singer’s management and publicity teams and wondering if Brown can ever truly regain respect.

Brown remains on probation for the Rihanna incident, so any legal issues become much more significant. Just this year, he was investigated and made to do 1,000 additional hours of community service when the service he supposedly completed was called into question. A fender bender in L.A., also this year, with new girlfriend Karruche Tran became news when it was revealed that Brown’s license was from Virginia, not California, and that he handed the other driver Tran’s license instead. The other driver later complained that Brown called her a bitch. (Charges were ultimately dropped). Neighbors in Brown’s Hollywood Hills neighborhood complained about “artistic” graffiti painted on his house, and his neighbors in an L.A. condo he previously lived in complained about loud music, dogs and Brown parking his cars in handicapped spaces.

Earlier this month, in yet another Twitter rant, Brown called out celebrity blogger Perez Hilton and Wendy Williams for talking about him on her show. All told, he’s keeping his lawyer, Mark Geragos, quite busy. The scene from this latest arraignment was reminiscent of many of Pac’s troubled media apperances– although Brown was more restrained than Pac was in some of his more scandalous moments. A front page photo of Shakur giving a photographer the finger after being shot in New York City is now classic.

Brown appeared almost frail as he was escorted out of the courtroom with security through a screaming crowd of “Team Breezy” supporters. He waved, but it’s clear from his appearance that his struggles are taking a toll. He no longer looks as happy or as healthy as he once did. It remains to be seen if Brown can have the cultural impact through his music that Shakur did. It also remains to be seen if the negative energy that dogs him will be dissipated by better choices and maturity or if the incidents will keep escalating, as they did with Shakur, leading to his untimely death on a Vegas street.

Fame comes with many rewards, but also with many challenges. Will Brown be the next Tupac? Only if he, or the people around him, continues to allow certain people, influences and situations to overrule his significant talent and erode what could be a legendary career. As many who watched Shakur’s stumbles in the 90’s recall, it’s a thin line between fame and infamy and it’s one easily crossed.