Jalen Rose and Wayne Brady speak to Bild and Dave Chappelle

There’s a reason Wayne Brady is an old-school, multidimensional talent who can seemingly do it all: singing, dancing, acting, improv comedy, hosting and producing.

First of all, the man works hard. And then there was his childhood.

“My grandmother didn’t let me watch much TV,” the Orlando, Fla., actor told me in this week’s “Renaissance Man.”

“So, the things that we saw was like a lot of PBS because she didn’t want me to see the things that she thought was fast at the time. So we ended up seeing the likes of Harry Belafonte, Sidney Poitier and Sammy Davis Jr. Sammy could drum. Sammy was a dancer. Sammy could act. Sammy could sing and speak. Sammy used to be able to embody anyone of his time. Sammy might sound more like Frank Sinatra than Frank Sinatra might sound like Frank Sinatra. He could shoot tricks and he could drive a racing car.”

Sure, the Let’s Make a Deal host studied comic book greats like Eddie Murphy, Richard Pryor and Robin Williams. But it was eclectic artists like Davis Jr. and Poitier who were placed on a pedestal at his home.

“I remember just loving Sidney Poitier and thinking, ‘This is what I want to be as an actor,'” he said. His approach was shaped by classic artists, and he’s undoubtedly a sophisticated gentleman, known for family-friendly network hits like “Whose Line Is It Whatever?” and “The Wayne Brady Show.” In other words, there’s nothing rough about Wayne’s image. And in the early days, the late legendary comedian Paul Mooney attacked him on “Chapelle’s Show,” saying, “White people love Wayne Brady because he makes Bryant Gumbel look like Malcolm X.”

It didn’t sit well with Wayne, who said the joke meant “we’re now policing ourselves. And he just questioned my blackness. The same black face that could arrest me, the same black face that could kill me, the same black face that kept me out of rooms because of my looks. I can’t wash it off. I can’t get rid of it I don’t want it, it’s nice. So I took it to heart. People would expect that to roll off my back. Forgive me, but fuck it.”

Using it as fuel, he turned the insult into a career-defining moment: a now-iconic “Chapelle’s Show” sketch, in which a seemingly sane Brady turns into a murderous, sociopathic pimp.

“I’m too proud of my accomplishments and I’m too proud of our accomplishments so I couldn’t give it up. So I was very happy that Dave reached out, he said, ‘Hey, I didn’t like that joke. Do you want to come and do this thing with me?’ And we got to write something that I’m proud of because it’s a fun skit. I will not question another black person’s blackness because of who she is.”

It was a brilliant move and made me a die-hard Wayne Brady fan. Shortly after that I flew to Las Vegas to see him perform, which I highly recommend, by the way.

But the story behind this sketch goes deeper, specifically the dynamic that exists in the black community where you’re an “Uncle Tom” or a sellout if you behave a certain way. I’ve been publicly guilty of this, calling Grant Hill and the Duke Ballplayers “Uncle Tom,” who is actually the hero of the story. It was immature and ill-informed. And sometimes the best way to teach that lesson is through humor—a medium Wayne has perfected.

And the Mooney line was a test too. How do you pick up a joke you don’t like? Are you a Wayne or a Will Smith now infamous for his Oscar slap? And Wayne had a lot of thoughts on that.

“I see someone who has laughed at all these jokes about his situation with Jada. I’ve heard rumors and everyone’s heard those things. How come it’s so famous that everyone wants to know what’s going on in your bedroom and have an opinion on it, especially black comedians. Everyone has a chance.” He noted that Will was the good guy who laughed and appeared on Jada’s laundry airs “Red Table Talk.”

LOS ANGELES, CALIFORNIA - FEBRUARY 10: Wayne Brady speaks onstage at Spotlight: Jimmie Allen at the GRAMMY Museum on February 10, 2022 in Los Angeles, California. (Photo by Rebecca Sapp/Getty Images for The Recording Academy)
Brady studied comics greats like Eddie Murphy, Richard Pryor and Robin Williams – but Sammy Davis Jr. and Sidney Poitier were put on a pedestal at his home.
Getty Images for The Recording A

“I think it was a matter of time. If it hadn’t been Chris Rock who said that joke – very stupid, low hanging fruit, not a funny joke – it would have been someone else at some point.”

Wayne is also honest that he too has struggled with issues that can lead to self-sabotage, like depression and imposter syndrome. He goes into therapy and practices mindfulness. And he’s not afraid to poke fun at himself and his drama tribe, either.

“Absolutely, theater kids can be unbearable. My daughter, she is studying theater at the moment. And she loves the theatre. She loves Broadway. She was raised that way. She always says to me, ‘Dad, I’m from the theater, but I’m not a theater kid. The theater kids are annoying.’” And I said, ‘I totally understand that, but you have to look at it that way. Theater kids are as annoying as some people find athletes annoying.’ I find some special interest groups, but mostly theater because [they] a whiff of outsiderness.”

And speaking of his daughter, maybe we’ll get to know 19-year-old Maile better soon. Because when I asked him if he’d ever add reality TV to his lengthy resume, here’s what he said: “If I had control of it, and that’s just the fancy way of saying, ‘You ain’t gonna catch me on the show, caught up in a house with people,’ and then, at some point, they say, ‘Well, whose alliance are you in?’ No, that’s not me. I think I work a little too hard for that. No judgement, I don’t want all the drama.”

However, he is developing a show with E! about his mixed familyconsisting of Maile, his ex-wife Mandie Taketa, her boyfriend Jason Fordham and their 7-month-old son Sundance-Isamu.

He does it because he can have his hand on the wheel and drive the show. Just like his iconic ride with Chappelle, only with less illegal activity. Although the fan in me is hoping it’ll be “I’m Wayne Brady, Bitch!”

Detroit native Jalen Rose is a member of the University of Michigan’s iconoclastic Fab Five that shook up the college hoop world in the early ’90s. He played 13 seasons in the NBA before blossoming into a media personality. Rose is currently an analyst for NBA Countdown and Get Up and co-hosts Jalen & Jacoby. He was executive producer of The Fab Five for ESPN’s 30 for 30 series, author of the bestselling book Got To Give the People What They Want, a fashion tastemaker, and co-founder of Jalen Rose Leadership Academy, a charter public school in his Hometown. Jalen Rose and Wayne Brady speak to Bild and Dave Chappelle


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