Wayne Brady: From Comedy To Broadway And Beyond

To call Wayne Brady the proverbial "triple threat" is really selling him short. Of course, he can sing, dance, and act, but there's much more to this man of many talents. He is hands-down one of the most versatile talents in Hollywood. Many people know him as the host of one of TV's longest-running game shows, "Let's Make a Deal." You might enjoy Brady's knack for improv comedy on "Whose Line Is It Anyway," a show he first appeared on in 1998.

But did you know he starred on Broadway as a drag queen in "Kinky Boots"? He's also a Grammy-nominated singer, and a Las Vegas headliner. Brady is an actor who can easily flip from comedy to drama. He appeared on "How I Met Your Mother" as Neil Patrick Harris' gay brother. More recently, he took on more dramatic roles in the Paramount+ series "The Good Fight," The CW's "Black Lightning," and Showtime's "American Gigolo."

Like many celebrities, Brady has opened up about some of his personal struggles over the years. He also has a refreshing take on relationships and family. The five-time Emmy winner says he likes to keep fans guessing with each new project he undertakes. "Every time I have a moment that makes people see me and go, 'Did he just do that?' Then I'm doing a good thing. That's a win for me," he told BET in 2013. Here's an inside look at his remarkable life and career.

Wayne Brady had a challenging childhood

Wayne Brady was raised in Orlando, Florida by his grandparents, who were from the U.S. Virgin Islands. He was a poor Black kid with a stutter, attending a predominantly white school, and the bullies at his school were relentless. "Either you break under that pressure as a kid, 'cause bullying is no joke, or you learn to take it and give it back, and do it in a way that gets a positive response," Brady told CBS News in 2013. "That's what acting was for me."

Brady admitted to Orlando Magazine, "From the time I could put a thought in my head, I knew I wanted to perform." But he didn't pursue it as a child for fear of being ridiculed. When his ROTC buddy dropped out of the lead role in a high school play, the teenager seized the opportunity to unleash his secret passion. "I saw it as a way to live my on-stage dreams, but at the same time not let everybody know that I really wanted to do it," Brady recalled.

After he got the acting bug, he began pursuing wherever gigs he could find. At the 2011 L. A. Comedy Shorts Festival, Brady explained, "I was doing a lot of theater, every little bit of theater that one could do in Orlando, every bit film that came through ... I was lucky enough to start working when I was 16." Ultimately, the "Girlfriends" actor's Broadway dreams turned into thoughts of a career in Hollywood.

He got fired from his first showbiz job

While Wayne Brady was going after every acting job he could find in Central Florida, he landed his first professional gig at Disney World playing Tigger. As he explained on "Seth Rudetsky's Back to School" podcast in 2020 (via Playbill), the young actor got a little too enthusiastic with his dance moves and passed out. Brady noted it was even more traumatic for the children who saw "Tigger die on Main Street." Meanwhile, his father, an army drill sergeant, wasn't a fan of his son's choice of professions.

"Rarely do you come from a household where everybody goes: 'Yay! You want to be onstage and be broke most of your life and live a life of uncertainty and maybe not have insurance?' Most parents don't do that," he told Playbill in 2015. In fact, they had a major falling out over it when Brady first started out in the business. His dad never even saw him perform in anything until 1993, when his son shot a two-episode arc of the CBS series "In the Heat of the Night" in Georgia.

Brady invited his dad, who was stationed in Conyers, Georgia at the time, not far from where the show was filmed. After seeing his son on camera, he finally came around. "This man couldn't have been more proud," Brady told Seth Rudetsky. "When it aired that summer, you would have thought that I won an Academy Award. Nobody trumpeted me louder than that dude."

His talk show was a flop

In 1993, Wayne Brady married Diana Lasso, and they parted ways two years later, per Closer Weekly.  At the time, no details about Brady's divorce were disclosed to the public. In 2019, "The List" actor recalled, "My first wife is a great person, but you should not be getting married when you're 20 or 21 because you still don't know yourself." For future relationships, he vowed to take his time before making such a serious commitment.

In 2002, ABC gave Brady his own daytime talk show. "That was the biggest thing in the world to me," he told Lee Cowan on CBS News. "I thought that I'd arrived." But "The Wayne Brady Show" went almost as quickly as it came. The network canceled the show in its second season due to dismal ratings, per CNN. In 2013, Brady told BET the series failed because the network wouldn't allow him enough creative input. "ABC wanted me to be the traditional talk show host, but I really wanted to talk about the things that I liked," he said.

"I'm a hip hop fan, I love the culture and I grew up in it. That was something I was never allowed to express and that's why I think this mostly lop-sided view of what I did on TV emerged," "The Masked Singer" alum said. "I wasn't able to really be me." The show was a critical success nonetheless, earning two Emmy Awards for Brady as Outstanding Talk Show Host.

Wayne Brady's second marriage worked out better

Wayne Brady married dancer Mandie Taketa in 1999, and they welcomed a daughter, Maile, in 2003. They divorced amicably in 2008 and remain close friends. "She is my best friend, my production partner and we made a beautiful baby, Maile, who's a wonderful young woman," Brady told Closer Weekly in 2019. During the early days of the pandemic, the family, along with Taketa's boyfriend Jason Fordham, all quarantined together. "For the entire duration of [my daughter's] life, we have coparented as best friends," Brady told Access Hollywood in 2020.

While they may seem like an aspirational couple, Brady says it didn't happen overnight. "Well, if you knew the fighting and the therapy and the tears and the work that it takes to make this look easy, then we've earned the right to coparent together and we've earned the right to have a blended family ... It's all about the work," he explained to Us Weekly in 2020. According to Page Six, Brady thinks of Fordham, a former backup dancer for his Las Vegas residency (which Taketa directed) as "a member of our family."

But after working together in Vegas, things weren't so cordial between the two men. "[Mandie and I] weren't together, but yeah, it was hard because I'm human," the entertainer told Page Six. "But because I'm also human, I learned from it."

Whose line is it, Wayne Brady?

In 1996, Wayne Brady made his Broadway debut as ruthless lawyer Billy Flynn in "Chicago," the role made famous in the film version by Richard Gere. But his breakout performance came two years later on ABC's improv comedy sketch show, "Whose Line Is It Anyway?"  Brady continues to be a frequent guest star on the series, and he earned an Emmy for his work in 2003. The comedian told Closer Weekly, "sharing the stage with Robin Williams and Whoopi Goldberg [was] just amazing."

Brady noted that the pressure to come up with funny material on the spot was no joke. "If you can't keep this space, if you're not getting a laugh every time you open your mouth, then you have no business being on that show," he explained to CBS News in 2013. More TV roles followed, including a stint as Officer Brady on "Vinyl Justice," a few episodes of "The Drew Carey Show," and a spot on "Reno 911!"

In 2002, Brady became the first Black host of the Miss America pageant, per Entertainment Weekly. He acknowledged that being chosen was "a defining moment," but added, "I'm the first African-American and that's great, but let's move on." Brady would rather celebrate his overall success on the small screen. "There hasn't been a year since I started 'Whose Line Is It Anyway?' [in 1998] that I have not been on a TV show, and I don't take that for granted," he told Closer Weekly.

Brady is cool playing gay

On the final season of "How I Met Your Mother," Wayne Brady had a blast playing James Stinson, Neil Patrick Harris' gay brother. Speaking to HuffPost, the actor broke down the details about his character. "He happens to be Barney's opposite and he happens to be gay and he's his brother who happens to be black." As for reaction from LGBTQ+ viewers, the actor said, "People in the gay community that have seen it know it comes from a place of love, that there's never any instance of camp. It's just about a guy."

Brady didn't hold back on the camp for his next role, however. In 2015, he took over for "Pose" alum Billy Porter, starring as Lola in the original Broadway production of "Kinky Boots." The role hit home for him, as he told Playbill before his debut. "Like Lola, I know what it's like to have people want you to be one thing, but you know that you're something else." Lola's father wanted him to become a boxer, rather than a drag performer.

Billy Porter won a Tony Award for his portrayal of Lola in 2013. "American Idol" alum Todrick Hall also took on the coveted role. Brady told Playbill this wasn't his first time putting on a dress and high heels on stage. He once went "complete Beyoncé drag" for a number in his Las Vegas show. "I'm hoping to get a lot of help in navigating the Kinky Boots part," he told Playbill.

The singer is a Grammy nominee

In 2009, Wayne Brady was nominated for a Grammy for his soulful rendition of Sam Cooke's R&B classic, "A Change is Gonna Come." After the release, some fans were surprised to hear the TV star's impressive vocals. "Wow, I always guessed Wayne could sing, but I didn't know he could blow like this!" one user commented on Whudat. Another person wrote, "This really was some beautiful soul singing."

In 2021, he recorded a track for Glenn Close on her spoken-word jazz album, "Transformation: Personal Stories of Change, Acceptance, and Evolution." For years, Brady had been working on a one-man show about the trauma he experienced growing up, but he wasn't making progress. "To be honest with you, the reason it took me a couple of years was because it was so painful," he told AP News. "Every time I'd go to it, I would start a draft and it got a little too real."

On the track, "A Piece by the Angriest Black Man in America (or, How I Learned to Forgive Myself for Being a Black Man in America)," Brady recounts the colorism he endured as a child from a lighter-skinned Black person in his neighborhood. "I had to deal with that person all my life until I realized I needed to forgive myself for whatever — for how Black that I felt I was, or how not Black that I felt I was," he added. "Those things were holding me back."

Wayne Brady became TV's top 'deal' maker

In 2009, Wayne Brady joined an American institution, taking over hosting duties for the reboot of "Let's Make a Deal," per Playbill. Monty Hall, who co-created and hosted the show for more than 20 years, advised him to always put on a happy face. "Love the people, because they're coming to your party," said Hall to CBS News. "I once said to Wayne when we were starting the show, 'If a woman is going for a car, and she loses it and still kisses you, you've done something right."

When Brady was offered the gig that earned him a third daytime Emmy, he turned it down — more than once. He didn't see himself as the "typical" game show host. "He has a long a** microphone and a suit that doesn't fit him well and he likes to say things like, "Fabulous!" I was like, "No, that's not what I do," Brady told BET in 2013. He finally came around when they agreed to make the show more fun — incorporating improv, songs and games.

When a contestant cashes in, Brady might occasionally qualify for hazard pay. As people "experience their happiness," he said, "I've been kicked ... out of love ... bear-hugged, thrown around, licked and pinched. I've also had my booty grabbed, my junk grabbed and I've been hopped on." Speaking to Orlando Magazine, Brady said the show works because it plays to the host's strengths. "That's why I think it has turned into this daytime party/improv/anything-can-happen/game show experience."

He struggled with depression for years

Wayne Brady is famous for his quick wit and sunny personality. But in 2014, he revealed he had been suffering from debilitating bouts of depression for years, and he was afraid to seek help. "Having a bad day is one thing, having a bad week is another, having a bad life ... You don't want to move, you can't move in the darkness," he explained to Entertainment Tonight. Brady said he continued to wallow in his misery and self-pity.

"This is what I deserve, so I am going to sit here because I am that horrible of a person," he continued. The "How I Met Your Mother" actor's 42nd birthday was a real low point. "I was there by myself, in my bedroom and I had a complete breakdown," he said. Speaking to Closer Weekly in 2019, Brady said he shared his story after Robin Williams' tragic death by suicide in 2014. "I thought that if someone who brings so much joy has the problem of loving themselves, then I can't ignore it."

Brady noted that his ex-wife, Mandie Taketa helped him get to a better place. "She was down with me when nobody in the world was down with me, except my mom," he told ET. In 2015, he filmed a PSA for Bring Change 2 Mind, an organization devoted to eliminating the stigma around mental health issues, per People. "I really wish that I would have spoken out earlier," he says in the TV spot.

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

The actor isn't so 'squeaky clean'

Wayne Brady does not like to be labeled. While he hasn't gained a bad reputation in Hollywood, he spoke to Arsenio Hall in 2013 about one title he takes issue with — being the "nice squeaky clean" Black guy (via HuffPost). "You know how it is, people place things on you. The thing is, I never asked for anyone to give me a squeaky clean image ... And I do a lot of stuff at night, and I tour, I do Vegas, and I do films that are adult," he said.

In 2014, Brady showed his edgier side, appearing in a now-famous sketch on "Chappelle's Show" as a foul-mouthed murdering pimp, per The New York Post. Besides his hosting gigs on Fox's "Don't Forget the Lyrics" and "Let's Make a Deal," Brady has taken on some serious acting roles in the last several years. Since 2020, he's been playing Gravedigger in The CW's superhero series, "Black Lightning."

Brady joined "The Good Fight," in Season 5 as Del Cooper, Liz Reddick's boyfriend, a comedian and streaming service exec. He was a big fan of the Paramount+ series, which stars Broadway vets Christine Baranski and Audra McDonald. Seeing "all these Tony winners and all this magic in one place? I was already hooked," Brady told AV Club. He also appears in Showtime's 2022 series "American Gigolo" which features Jon Bernthal in the titular role. Working with "The Walking Dead" alum, Brady told Instinct, "was a dream come true."

The entertainer is a fierce competitor

In 2019, Wayne Brady won Season 2 of Fox's musical competition series, "The Masked Singer," playing the character of The Fox. "The fox uses its brains in nature to succeed against bigger animals, and that's how I think of myself," the multi-talented performer told Variety after the win. After seeking his family's blessing to do the show, he had to convince himself he could walk away with the trophy. "There's no reason to do it if I don't think I can win it," he added.

In 2022, Brady joined the cast of another celebrity competition show, "Dancing with the Stars." This time around, he had one thing on his mind — the coveted Mirror Ball. "I'm going after this. And that's what's going to happen — just like I did 'The Masked Singer' [and] just like I have done in my career," he told People on October 25, 2022. Speaking to reporters after that week's episode, Brady admitted he thought about throwing in the towel after fighting a cold at one point.

He even questioned if he was just spinning his wheels as a competitor. "Part of it is truly physical and then the other part is — and this is my favorite part of this show — it places you in an uncomfortable place where you may not be used to. I'm used to shining in everything that I do hands down," he said. Brady and his partner, Witney Carson, scored 44 out of 50, putting them in fifth place for the night, per Just Jared.

Wayne Brady is a total 'girl dad'

Wayne Brady's daughter Maile is following in her father's footsteps, and he couldn't be any prouder of his only child. As a youngster, she appeared as Brady's daughter in his music video for "You and Me," a track on his 2008 "A Long Time Coming" album. They dance on social media together, and they both had roles in the long-running soap opera, "The Bold and the Beautiful."

"I think [the] dream is if we could be on Broadway together," Brady told ET in 2018, when Maile first stepped into the role of Tiffany on "B&B." Dad and daughter shared the screen on the daytime drama the following year, with Brady playing Dr. Reese Buckingham, per People. He spoke to CBS about why the series holds a special place in his heart. "It was appointment viewing for myself and my grandmother," he said (via People).

"Cut to Maile getting to play a role on the show that I loved, and that so many great actors have come out of? It's just thrilling," he added. Brady admitted he had a heart-to-heart with Maile before signing on to do "The Masked Singer." "My daughter and I are kind of talent snobs," he told Variety with a laugh. In a sweet 2020 Father's Day tribute, Brady captioned a family pic on Instagram, "Being a father is THE most important job I have. I love it."