The Complete Transformation Of Wayne Brady Through The Years

Wayne Brady does it all. He's a singer, a dancer, an improv comic, a game show host, an actor, and more. He's been in movies, on Broadway, and on many television shows, and he loves any chance he gets to perform for people. As Brady told Verywell Mind, "I don't choose any one thing because I'm lucky enough that that's what my gift is. I wouldn't be having this conversation with you if I weren't an actor who also improvised and sang and danced, because they all [create] a whole and it's always been one lump sum to me, in a good way."

For that reason, Brady's career has been one of constant transformation, surprising audiences year after year with each new endeavor. That said, he doesn't often share too much about himself with the public. "I think the problem with a lot of folks in showbiz is, you know too much about them," he said in a behind-the-scenes featurette for his first album. "But I'm not in a tabloid every other minute, so you don't know everything about me. Which makes me incredibly happy."

Though Brady likes it that way, such a prolific career means it is possible to track his changes and talents over time. Read on for a look at the complete transformation of Wayne Brady through the years.

Wayne Brady had a difficult childhood

Wayne Brady's upbringing was strict. "My dad, God bless his soul, was for most of my life an Army drill sergeant: very G.I. Joe and by the book," he told Playbill. He said he loved his father, but his father didn't understand his natural tendency toward being a performer. "I was growing up in the kind of household where a performing arts career wasn't practical," he recalled.

Then, Brady was sent to live with his grandmother. She, too, was tough on him. Fearing the drug problem in their town, Brady's grandmother insisted on a measure of control over his life so that he didn't fall in with the wrong crowd. "She feared for my safety. So she made me stay indoors. She didn't let me go outside. I couldn't play with other kids much. I had to come right home from school," he explained on the Imposters podcast. However, Brady now tries to see the good in that. "[I]t did two things. It made me very self-reliant, and I was able to self-motivate and self-play," he reflected. "And I think it triggered my imagination."

One of the ways he put that imagination to use was in school plays. He was cast in "A Raisin in the Sun," and he loved it. "It was absolutely amazing," he told Verywell Mind. "And so, I thought, 'oh, this is what I'm going to do for the rest of my life,' because I was very naive."

He was bullied as a kid

While Wayne Brady was struggling in his home life, he struggled in school too. He had a bad stutter as a kid, which led to bullying. "It was bad enough to where I really did not want to talk to too many people because I would get so worked up," Brady told CBS News. He was later honored by the American Institute for Stuttering, but he told the 2017 gathering that he nearly didn't accept, because he didn't want to admit — to himself or to others — that he stuttered. By attending the gala, however, and meeting other people who had gone through the same things he did, he realized that he'd had to teach himself how to get around his speech difference as a child. Still, he couldn't help but bring up his memories of the bullying he endured as a result. "As a kid, when I stuttered, I would hear the other kids make fun of it, and that pretty much cemented how I felt about stuttering, and that shame, even now," he confessed.

The way Brady dealt with the bullying he experienced was to develop his quick-witted sense of humor. "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," he explained to CBS News. "That what acting was for me." 

Wayne Brady worked at theme parks as a teenager

Wayne Brady lived in Orlando, Florida, as a teenager, so as he discovered his love of performing through school plays, he put that talent to use in some of his first jobs. Brady worked at Walt Disney World and Universal Studios, playing characters as varied as Tigger, Dracula, Goofy, and Winston from "Ghostbusters." He liked the way his theme park roles let him disappear into his characters, telling People, "I loved that because you see the work. You don't necessarily see me. I love bringing joy, which is why I love being a character."

Brady disappeared into his Disney characters in another way, too: The costumes let him interact with people who wouldn't necessarily have trusted him otherwise. On "Ziwe," he noted that "mainstream America" is more comfortable with a Black man in a costume than one in a fedora. "Rednecks would take their kids and shove 'em in my arms," he recalled, suggesting that this would not have happened had they known who was under the mask.

Ultimately, Brady was let go from Disney World in an incident that he says wasn't his fault. He told "Stars in the House" that he encountered someone claiming to be a park executive who wanted her kid to jump the line to meet Tigger, and when he politely refused, she had him fired for pinching her son, which he didn't do. After all, he said, the Tigger gloves are "basically oven mitts."

Whose Line Is It Anyway? brought him his big break

Throughout the '90s, Wayne Brady's entertainment career was on the rise. He worked in various theme parks, including a stint as Tigger at Walt Disney World. He was an extra in "Earth Girls Are Easy" and popped in for small roles on shows like "Clarissa Explains it All." Then, as the '90s drew to a close, Brady was hired for a few episodes of the British version of "Whose Line is it Anyway?" The show filmed in America anyway, so when they launched an American version in 1998, Brady was an easy choice for a part of the regular cast. The show was a hit. "It was something most of mainstream American hadn't seen before," he reflected to The Register-Herald

On the show, host Drew Carey explained at the top of every episode that "everything's made up, and the points don't matter," Brady and his castmates would play games, improvise scenes, and perform musical numbers on the spot. Brady was particularly great at the latter, devising whole songs based around members of the audience.

After being nominated three years in a row, Brady finally won a Primetime Emmy for his work on the show in 2003. Looking around the room as he accepted the award for individual performance in a variety or music program, he said, "Thank you to you guys, for letting me make you laugh."

He hosted The Wayne Brady Show

Wayne Brady was the breakout star of "Whose Line Is It Anyway?" and in 2001, he got the chance to step out on his own. Brady hosted his own variety show, fittingly called "The Wayne Brady Show." The show featured celebrity guests like Justin Timberlake and Chris Rock, and Brady would sing, do impressions, play improv games, and interview his guests. TV writer Buz Kohan, who worked on the show, had nothing but glowing things to say about its host. "Wayne [is] a tremendous talent, very, very skillful, very charming, very delightful person to see and to meet and to spend time with," he told The Archive of American Television. "Energy. Great adlib ability. Sings, dances ... it was almost the next Sammy Davis, kind of thing."

Brady was ecstatic about the fact that he was leading his own variety show. "That was the biggest thing in the world to me," he told CBS News. "I thought that I'd arrived." The industry seemed to agree, at least at first; he picked up Daytime Emmy Awards for Outstanding Talk Show Host in both 2003 and 2004. The show was ultimately canceled that year; luckily, he still had "Whose Line?" to fall back on.

Wayne Brady became a father in 2002

In 2003, while Wayne Brady was still on "The Wayne Brady Show" and "Whose Line is it Anyway?" the multi-hyphenate added another impressive descriptor to his name: father. Along with his second wife, Mandie Taketa, Brady welcomed his daughter Maīle Masako Brady in February of that year. The couple told ePregnancy Magazine that Brady had always wanted kids, but his wife had been hesitant. She told him she was pregnant just after his birthday, and he was so emotional that he cried. "When she said she was pregnant, I was like, 'Shut up, no, you're not!' And I said, 'Mandie, stop kidding me — that is so mean — trying to kid me about something like that,'" he recalled. "All of the sudden, I'm crying, because it was just incredible."

Though he and Taketa would ultimately divorce — more on that below — Brady remains very involved in his daughter's life. He frequently shouts out her accomplishments on social media and often posts photos of her as a young girl. On Father's Day in 2023, he shared some throwback pics on Instagram and wrote, "Maile, you make every day possible for me. There is no greater joy than being your Father! I love you little buddy! I love the incredible little Monkey that couldn't let go of my hand to the amazing woman you are."

Wayne Brady starred in an infamous Chappelle's Show sketch

When Wayne Brady skyrocketed to fame thanks to his appearances on shows like "Whose Line is it Anyway?" and "The Wayne Brady Show," he bristled at criticism that he was too wholesome. In an effort to give his public image a little more grit, Brady appeared on "Chappelle's Show" in 2004.

A few episodes earlier, comedian Paul Mooney had joked, "White people like Wayne Brady because he makes Bryant Gumbel look like Malcolm X." Brady wasn't a fan of this and said it offended him. "I get offended from a bigger level, in the fact of Black people, we are one of the only races that I feel, if someone is judged as not being Black enough," he explained to Michigan Live. "People take it to be, 'Ugh, look at him. He only got there because white people put him on.'"

Chappelle invited him to do his own sketch, and he would go on to utter the now-infamous line, "Is Wayne Brady gonna have to choke a b****?" People still quote the line to him to this day, he told CBS News. "When people go, 'But that's just not you,' that's why it's so funny. You don't know me. Till the day that I die, I will constantly say, 'Do not define me by that.'" His ability to speak to multiple audiences, he told Michigan Live, is a strength. He summed up his approach by pointing out, "Funny is funny."

Wayne Brady got divorced twice

In 2007, Brady divorced Mandie Taketa, his second wife. "I'm a cautionary tale," he told Yelp's Black in Business Summit in 2022. He was so focused on his career in the 2000s, taking all of the opportunities that came his way, that he didn't make his relationship a priority. "[I]n the middle of building and in the middle of trying to do that, if you don't pay attention to your home life, what are you working for? And I got divorced," he said. He and Taketa remain extremely close, and Brady told the summit that he does still consider her his soulmate. "I was very, very lucky, but we couldn't remain married anymore because I was not tending to the fires at home," he said.

Brady and Taketa stayed best friends after their divorce, to the point that Brady isn't just co-parenting his daughter with his ex-wife; he's helping raise her new son, too. On Instagram in 2021, Brady revealed that Taketa had welcomed a son with her new partner, and they asked Brady to function as a third parent. "They say it takes a village to raise a child and they're right!" he wrote. "All children will know is love if that's what you show them. I'm honored to be in his life as his 'Duncle' and I love Mandie and Jason for including me in their journey."

He became a recording artist

Wayne Brady doesn't just sing improvised songs on "Whose Line Is It Anyway?" He's a recording artist in his own right, having released an album called "A Long Time Coming" in 2008. The album's title had two meanings. First, it's a lyric from Sam Cooke's "A Change Is Gonna Come," which Brady covered on the album. Also, Brady felt it was about time for him to get started on a musical body of work. "This album is about seven years behind schedule," he said in a behind-the-scenes featurette.

Brady received a Grammy Award nomination for his cover of "A Change Is Gonna Come," competing in the category of best traditional R&B vocal performance. He told CBS News that he was overwhelmed with emotion to be recognized by the Recording Academy for his first album. "I cried to myself," he confessed. "I called my mom and I cried. I knocked on my little girl's room and said, 'Daddy whaa whaa whaa!' Big deal in my household."

He didn't win, and the album's sales were not particularly successful (it peaked at No. 157 on the Billboard 200 albums chart). Nevertheless, Brady's record label boss, Andi Howard, told Singersroom that they were happy. "Not only did he deliver a fabulous album, but an album that is extremely heartfelt and exceeded all expectations," Howard said. An album of children's music, "Radio Wayne," was released in 2011. His third album was promised for early 2020 but still hasn't yet materialized.

Wayne Brady hosted Let's Make a Deal

The original run of "Whose Line is it Anyway?" ended in 2007, but in 2009, Wayne Brady returned to television. He became the host of a revived version of "Let's Make a Deal," a game show in which contestants bargain with the host to hopefully win bigger and bigger prizes. The contestants often wear elaborate, deeply silly costumes, and the show gives Brady the opportunity to improv with his guests. He even sometimes breaks into song the way he used to on "Whose Line?"

The show films in Las Vegas, where Brady also had a nightly variety show at the time. "You just make it work wherever you can because it's a feast or famine thing. And I'm lucky that, for the duration that I've been on TV, it's been a feast," he told Boston Herald of his hectic work schedule. "So I'm the last person to complain." He told the outlet that he didn't feel much pressure as one of the only Black game show hosts, explaining, "I think the responsibility is for me to be the best possible host and to ride this show into 10 years from now."

The show is indeed still on the air. On the occasion of its 1,000th episode, Brady went on "CBS This Morning" and spoke about what a good time he has on set. "We make people smile," he said. "It's really such a unique job."

He's a mental health advocate

In 2014, Wayne Brady opened up about his experience with depression. In an emotional interview with Entertainment Tonight, Brady revealed that he had "a breakdown" on his birthday that year. "I was there by myself, in my bedroom, and I had a complete breakdown," he said. "Just go ahead and imagine for yourself a brother in his underwear, in his room, you got snot ... and that birthday was the beginning of, 'OK, I've got to make a change.'" He was also affected by the passing of Robin Williams, who died by suicide that year, and it led to him wanting to open up.

In the years since he first went public, Brady has become a mental health advocate. He made a video for the Child Mind Institute about his experience, speaking directly to his younger self. "I would just say, please, talk to someone. And just know, there's no shame in it. Secrets kill. Keeping this a secret? That's the worst thing you can do."

In 2022, Brady spoke with Verywell Mind about how he was doing, years after first starting to talk about his mental health. "I'm very open about it because I feel that the only way to get help for some people is to look at someone else," he said. "[This] isn't the beautiful end of a story and then I'm fine ... It is a work in progress."

Wayne Brady starred in Kinky Boots

Wayne Brady made his Broadway debut in 2004, playing Billy Flynn in "Chicago." More than a decade later, in 2015, he took on the lead role of Lola in Cindy Lauper's musical "Kinky Boots," and he told TheaterMania that he felt like this was his actual Broadway debut. "It's a different experience," he explained. "Playing Billy was summer camp for me ... But this is real work."

Brady's character Lola is a drag queen, and that meant performing onstage for lengthy amounts of time in the show's titular high-heeled boots. "I didn't realize exactly what it takes to dance in heels. There's an art," he explained to Theater Mania. He showed off his pre-show routine on Instagram, posting a video of himself in full costume and makeup using a foot roller to prepare himself for the physical strain necessary for the performance.

The "Bold and the Beautiful" star also hit back at critics online who said he shouldn't have taken the role, insulting his masculinity for having done so. "I wrote back to people online, saying: 'Well, I really don't care,'" he told UPI. "'I don't need your permission to do this. I'm glad that you're a fan, but if you are really a fan who doesn't like me right now because I'm dressing up in a dress without you even knowing what the show is, then I don't need you as a fan.'"

He won The Masked Singer

In 2019, Wayne Brady competed on the second season of "The Masked Singer" while dressed like a steampunk fox. He performed songs like Chris Stapleton's "Tennessee Whiskey" and Maroon 5's "This Love" so well that he made it all the way to the finale, ultimately taking home the top prize. "This has been the coolest, most amazing, most touching, most challenging, weirdest — and I host 'Let's Make a Deal!'" he joked after being unmasked. "But, God, I mean, really? I'm gonna take this with me forever."

Brady elaborated on his experience in an interview with Variety, revealing that his daughter and ex-wife were two of the only people he told about "The Masked Singer." His daughter wasn't sure about his participation at first, but he won her over through his commitment to showing off his talent every week. He told the outlet that people at school called her "Little Fox," and she had to lie to her friends that she had no idea what was going on. "She also thinks it's really cool because not everybody can say they have a parent doing a show that everyone is talking about," Brady said. "She is 100% behind me and she is my biggest fan."

Wayne Brady came out as pansexual

In August 2023, Wayne Brady came out in an interview for People. The funnyman identifies as pansexual, meaning he identifies as someone who can be attracted to anyone regardless of their gender identity and expression. "[T]o me, pan means being able to be attracted to anyone who identifies as gay, straight, bi, transsexual, or non-binary. Being able to be attracted across the board," he told the magazine. "I took pan to mean that not only can I be attracted to any of these people or types physically, but I could be attracted to the person that is there."

Brady's family supports him as he claims this for himself. "I just said, 'Great,'" his ex-wife Mandie Taketa told People. "As I knew coming out would help him be happier." His daughter Maīle Brady agreed, recalling that she simply told her father, "Okay!"

Alongside his coming-out announcement on Instagram, Brady shared a TikTok in which he lip-synched Celine Dion's "It's All Coming Back to Me Now." He donned a wig for the video, performing in front of a rainbow light. "This shouldn't shake anyone's world, but if it bothers you at all, that's your business," he wrote. "I was so afraid of having my manhood questioned, but screw that. A 'real man' in my eyes isn't afraid to be honest and happy. From now on," he concluded, "I'll be over here living my best life!"