His most recent brush with the law — he was arrested for assault with a deadly weapon on Tuesday — could land him a lengthy prison sentence for the first time in his career if he is convicted. But with his cultivated "bad boy" image and nearly 17 million followers on Twitter, will his career suffer for his myriad of transgressions?
"It's all about connecting with your audience. If his fans don't mind or admire his bad boy behavior, the circumstantial publicity keeps you on the pop culture radar," brand expert Karen Post told NBC News. "On the other hand if an orange jumpsuit is in his future, performing to a few convicts over big arenas will hurt his bank account."
Certainly, law enforcement may be running out of patience with the singer, who appeared to cloak himself under the veil of the Black Lives Matter movement while lamenting what he considers to be biased treatment by local police on social media in the lead-up to his arrest.
"Every three months, y'all come up with something, bro. What is it? What's going to be next?" Brown wrote on Instagram, adding: "At the same time, when I call police for stalker people … they don't come until the next day."
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Brown is accused of threatening Baylee Curran with a gun at his home Tuesday in Los Angeles. After being booked, Brown was released from jail on $250,000 bail. Curran appears to have an open complaint against her for the alleged theft of a wallet and cash in 2013, according to KNBC.
According to Amber J. Phillips, co-director of the digital firm BLACK and a reproductive rights activist, Brown is not the best mouthpiece for criminal justice reform.
"Chris Brown is a black man, and I do not want to see him get into trouble with the state or be murdered by the police. But there is this other piece of accountability when it comes to folks like Chris Brown," she said. "He has to hold himself accountable for this toxic approach to masculinity."
"I love the movement for black lives so much, because it's pro-queer, it's pro-women, it's pro-trans people," she added. "Those are the additional pieces that folks like Chris Brown are missing."
And yet, these nuances appear to be lost on Brown's aggressive, predominately female fan base, known as "Team Breezy." The singer's followers are infamously vicious online. In fact, Brown himself had to plea for them to stop making death threats against model Chrissy Teigen online in 2012 after she made light of his "fits of rage." Comedy writer Jenny Johnson was also subjected threats of violence by Team Breezy, after a confrontation with Brown on Twitter led the singer to briefly quit the social media platform.
Even more disturbing were a series of tweets that accompanied Brown's performance that same year at the Grammys, in which multiple female social media users shared variations of "he can beat me" sentiments.
"I think a lot of folks practice selective amnesia when it comes to Chris Brown and all other stars who have been accused of wrongdoing. Fans either choose to, or just so happen to, forget his past because he has somehow swooned them and given hope that he'll, one day, do better. His music also has a lot to do with that," Lilly Workneh, the senior editor of Huffington Post's Black Voices, told NBC News. "However, despite falling short on his promise, people continue to look to his potential future and ignore his troubled past and as long they do, I think fans will continue to support him ... and that's troubling."
When it comes to his female supporters, Phillips said that Brown and, to a certain extent, actor-director Nate Parker (who has come under fire for resurfaced 1999 rape allegations, of which he was eventually found not guilty), can force uncomfortable conversations about the role women can play in perpetuating misogyny.
"Racism and patriarchy are close cousins," she said. "Blacks can support hateful white ideology — we're not a monolith. And the same thing can happen with women, we can be allies in patriarchy."
Phillips believes that women and men must hold Brown accountable, and hopefully force him to make the kind of public mea culpa Parker has been in the midst of.
But average citizens also need allies in the entertainment community, which means Brown's peers in the record industry (who often deploy him to sing their hooks) will need to step up, too.
"We need other artists of his caliber, of his scale to take a pause and have these conversations," she said. "They need to stand up and say, 'You can't slap a woman or pull a gun on a woman and be on our tracks.'"
"We have to keep critiquing," Phillips added, admitting that she had grown up being a fan of Brown's music and had to reconcile his talent with the reality that he has abused women. "I believe you can critique what you love."