Fellow bad boy Justin Bieber has been tarred with a similar brush: despite his numerous attempts to clean up his image (including a Men's Health cover story proclaiming how he has evolved from a boy to a man in the last 12 months), he continues to be plagued by accusations of molestation and sexual harassment.
Can bad boys change? Brown and Bieber are certainly trying to publically prove it's possible, whether efforts are through tweets and anti-violence advocacy or by personally taking part in Comedy Central Roasts, which poke fun at demonised celebrities' pasts.
Bieber's roast, for example, was an attempt to acknowledge his scandalous behaviour from his younger years, laugh at himself, and - together with the world - move on from it.
It wasn't terribly well received by critics, though. Bieber was noted as appearing discomforted and awkward throughout much of his performance.
Therein lies the problem with bad boys' publically remorseful actions: they are undoubtedly cooked up by managers and PR teams in a bid to ensure the talent remains profitable.
Just because something is an orchestrated PR effort, however, doesn't necessarily mean the intentions are disingenuous. But in the case of Brown, with an upcoming tour that would lose promoters millions of dollars, it's easy to see that his latest wave of atonement could be a by-product of his labours, not his primary goal.
So begs the question: should they be taking another tack?
While celebrity bad boys like Brown and Bieber aren't new, their aggressive attempts to reinvigorate their reputations are.
Historically, celebrity bad boys have proven they've moved on from their rebellious behaviour not by active campaigning, but by becoming reclusive for several years, letting society forget their ways, and coming back with a vengeance.
Former Hollywood bad boy Robert Downey Jr. is the most successful example of this to date. His drug addiction and arrests were well-documented throughout the late 1990s, and his career low point was undoubtedly in 2001 when he was fired from his role on Ally McBeal just hours after being arrested on drug charges.
Downey Jr. went quiet for years, until the Iron Man franchise cropped up in 2008 and he once again became a household name.
Fast forward to 2015, and he is the highest earning actor in Hollywood. Quite the turnaround for man who once literally lived life in the gutter.
Similar reclusive behaviour has proven successful for now-former bad boys such as Sean Penn, Johnny Depp, Jared Leto, and Colin Farrell.
The trouble with Brown and Bieber is this: They've remained in our faces. They've given us no time to forget their bad behaviour. Instead they have continued to push out records, continued to do promotional rounds, and continued to relentlessly tour.
Because they retain high public profile, they remain a target for media, and also for anybody who wants to "go public" with a demonising story that further enhances their bad boy status.
While they may be concocted by a team of PR professionals, any exuberant apologies, cover stories, roasts, and speaking engagements are a PR mistake for bad boys.
If you're in the public eye, you need to give it years - if not a solid decade - before you can prove you're a bad boy gone good.
Such a strategy isn't one we're likely to see from the current wave of early 20's bad boys for one simple reason. They don't have enough of a career behind them to risk going bush.
If Bieber or Brown went quiet until 2025 and re-emerged as thirty-something pop stars, they would likely be laughed out of town and be relegated to Where Are They Now?-type listicles and TV specials for the rest of their lives.
We can't write Brown and Bieber off just yet, because when you put their reputations aside, people still do like their music.
However if they really want a chance at longevity in show business, they'd do well to continue their remorseful efforts when the cameras stop rolling and there isn't such an obvious buck to be made out of them.
