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Katt Williams is no stranger to roasting others on stage. Some might say that being good at roasting people with quick comebacks is a part of being a comedian. But there was one roast he hosted where he felt he and other comedians took jokes in the wrong direction. And he was mad at himself because of it.

Why Katt Williams once roasted radio host Wanda Smith

Katt Williams smirking while wearing a suit.
Katt Williams | Jason LaVeris/FilmMagic

Katt Williams has shown the ability to roast with the best of them. This was evident when he stopped by the radio station V-103, where he ended up getting into a verbal altercation. V-103 radio host Wanda Smith found herself trading barbs with Williams, with many feeling that the comedian got the upper hand. Speaking to The Ringer, Williams explained the motivation behind the roast.

“This person comes to me and tries to make it, ‘Katt, can’t you say hi to your people? Atlanta loves you, I represent Atlanta, and you just won an Emmy for Atlanta. I don’t want to talk about your personal life, I don’t want to talk about your kids. I just want to big-up you to my crowd.’ That’s how this was set up,” Williams said.

But to Williams, Smith approached topics that they already agreed not to talk about.

“So automatically when she goes into kids and whatnot, it’s already off the rails at that point,” he continued. “I’m telling her, ‘Ma’m, I’ve watched you and your response when my name is brought up on your channel.’ It’s the fact that she went out of her way to say that wouldn’t be the case.”

Despite Williams roasting the radio host, he also explained how he showed restraint with his response to Smith.

“My job was to use no curse words to not demean her in any way,” he added.

He also asserted he wasn’t the type of comedian to roast others. However, a while back, Williams was recruited to host the roasting of another famous celebrity. But it was a roast that he didn’t enjoy.

Why Katt Williams was upset with himself after roasting this famous celebrity

In 2007 Katt Williams hosted the Comedy Central roast of hip-hop superstar turned Reality TV star, Flavor Flav. To host the television special, Williams had to follow a script. But unfortunately, the material Williams was given wasn’t to his liking.

“[The script was] racist like a 1947 newspaper,” Williams said in an interview with the New Yorker.

He would later compare the roasts of other celebrities and the roast of Flavor Flav to illustrate his point.

“I saw the William Shatner roast, and the Pamela Anderson roast, and it wasn’t all about them being white,” the comedian asserted. “But on Flavor Flav’s s*** every other word was ‘Flav is a crispity, crackly, crunchety coon.”

These kinds of jokes didn’t sit right with Williams, upsetting the comedian.

“I was mad at me, that I was still f****** doing it, the way I felt,” he shared. “But they had already told me how much they were gonna pay me, and I had already spent it. In my head.”

According to Williams, he spoke with Flavor Flav backstage after the Comedy Central roast.

“I don’t give a f*** what they think – they got to pay me,” Flav said, although it’s worth noting that Flav’s press denied this.

However, Williams stated that he learned something valuable thanks to the whole situation.

“If they was gonna call you a crispity, crackly, crunchety coon anyway, you might as well get them m***** f****** for e-ve-ry-thang. E-ve-ry-thang? E-ve-ry-thang,” he said.

Why Flavor Flav took Chris Rock’s jokes personally in his Comedy Central roast

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Speaking to DJ Vlad, Flavor Flav had fond memories of the comedy central roast hosted by Williams.

“Me and Katt Williams have always been good friends too,” Flav said.

He later tried to recall a joke Williams tried to do on the artist where Williams said “’At the end of the day, all Flav wants is his money,’ or some s***.”

However, he had more of an issue with comedian Chris Rock, who he felt was getting a bit too personal.

“When he started clowning on me, I kind of took offense to it. Not thinking, ‘Hey, this is comedy.’ I’m thinking, ‘Hey, this guy is lashing out on me,’” he said.

But Flav later realized why Rock roasted him the way that he did.

“But then again, in order for him to be somebody, he has to pick on somebody. So I was the somebody that he had to pick on in order for his ass to be somebody,” Flav told Vlad.