Before that, people thought he was a nice guy. He had to be, right? He was just a kid who sang songs about girls and dancing. No one would've predicted he could turn out so bad.
I was definitely surprised when it happened - it was a crazy story - but most people were really shocked. My reaction just wasn't as extreme because I had seen this before. Back in 2006, I was watching an MTV Cribs episode starring K-Ci & JoJo. I was interested to see them in this setting - I liked their songs, but I had never seen them do anything but sing. As it turned out, they couldn't have been further from what I was expecting. They acted more like the Ying Yang Twins than a couple of guys who sang love songs. It was hard to even imagine how "Tell Me It's Real" could have come from their mouths.
Somehow, I felt a little deceived. I guess I thought songs had to be true. For some reason, I figured a singer's personally would have to match his songs. But I was young and naive back then. Now, I realize that's ridiculous. Other people write songs, and they sing them. They're just people... and some people are assholes.
K-Ci and JoJo taught me that lesson, and they weren't even bad. They just drank too much; they didn't really hurt anybody (as far as I know). It turns out, there have been plenty of other singers who ended up being actual thugs. And some of these guys have done some real dirt.
Frank Sinatra was more of a wanna-be thug, but he did hang with real thugs, which sort of makes him a thug by association. Sinatra was fascinated by the exploits and lifestyle of those involved in organized crime. He became friends with some of the baddest mob bosses of the day, partying with them, performing for them, and (allegedly) completing some tasks for his mafia friends. While his involvement in any criminal activity is unproven, his relationships were well-known facts - he was even interrogated by the FBI after spending time at a mob summit in Cuba. Whether or not he committed a crime is irrelevant. The point is that Ol' Blue Eyes idolized men who robbed, trafficked, and killed for a living.
With songs like "I Believe I Can Fly", R. Kelly hid his thugness long enough to get some hits under his belt. Though he had already been charged with battery in 1997 (forcing the victim to require 110 stitches in his face), the veil was completely lifted in 2002. In that year, Kelly was arrested for allegedly having sex with, and pissing on, a teenage girl. Shockingly, he was exonerated (though he videotaped this incident), but the nice-guy image was gone. In a way, you could say he was set free - free to let his real personality show, and unleash his true thugitude from then on.
By now, everyone has heard all about the Rihanna incident. But since then, Chris Brown hasn't let up at all. Besides being a general hot-head/asshole, he has also violated his probation multiple times and participated in separate violent altercations with Drake and Frank Ocean. And he's still young. Surely, there's plenty more thugness to come.
So, it's pretty clear that James Brown is the biggest thug of this bunch. In addition, he's also hands-down the worst husband (he also fathered "at least three extramarital children"), and the subject of one of the worst mugshots in history.