When Wayne Brady won the second season of the Fox reality show singing competition “The Masked Singer” in December, it was the latest entry on one of the most diverse resumes in contemporary entertainment. In the two decades since he moved from Orlando, Fla., to Los Angeles, Brady has distinguished himself is a singer and actor, Broadway performer and television show host.
Brady appeared on Broadway as Lola, the transvestite star of the contemporary musical, “Kinky Boots,” played Aaron Burr in the Chicago production of “Hamilton” and displayed his talent as a hip-hop poet and improv performer on Broadway as a cast member of “Freestyle Love Supreme.” He is also in his 11th season hosting the perennially popular CBS game show “Let’s Make a Deal.”
Since winning “The Masked Singer” Brady has released a new video single, “Flirtin’ With Forever” and played Tyson “Gravedigger” Sykes in The CW’s DC Comics drama series “Black Lightning.”
At the end of December, he recorded a music video medley, “Tennessee Whiskey”/ “A Change Is Gonna Come,” with the veteran island duo Simple Souls at Aloha Beer Co.’s HI Brau Room in Kakaako. (The video is posted on Brady’s Instagram account @mrbradybaby.)
Brady, 47, is working on a collection of recordings he plans to release later this year. He returns to Hawaii for two nights at the Blue Note Hawaii on March 7 and 8.
“The Masked Singer” may feel like ancient history two months later, but could they have taken any longer than they did to reveal you were the winner?
Every reveal was like that. It was going along with the music. It was like, “I can’t get it off! I can’t get it off!” (Referring to the costume worn during the competition.) But that was part of the fun.
Jumping from “The Masked Singer” to your unmasked singing career, that’s such a beautiful music video recording of the “Tennessee Whisky”/ “A Change Is Gonna Come” medley with Simple Souls.
With my friends JRoQ and Zaysha. I met them at the Alohilani Hotel several years ago. I was in my room sleeping and Mandie, my ex-wife, was here with my daughter, Maile, and Mandie’s boyfriend, Jason, and she told Jason to come and get me because there was this amazing band downstairs. I was already asleep but I went downstairs and just immediately fell in love with their voices and their singing. (JRoQ) is such an amazing musician, and together as a duo they are so pure. So much pure talent. Recording that video was my pleasure to do with them, and I’m going to be releasing a teeny bit of another video that we did together. We did an island version of my current single, “Flirtin’ With Forever,” and it was pretty damn cool.
Can you share any insider information about “Flirtin’ With Forever?”
An interesting bit of trivia — at least interesting for me — is that the woman on the record cover is my grandmother when she was 35 or something. It actually is a vintage Polaroid.
Is this a return to music for you?
Music has always been a part of my career — since I was a kid, since I started doing music — but once people get to know you for one thing that’s what you are in their heads. You have to educate them. And I found myself getting to a place where I started to feel self-conscious if I sang a song that wasn’t something funny because that’s what I felt the expectations were. I needed to get over that ridiculous mental hurdle because what I do is what I do, and who I am is who I am. I can’t let that be shaped by thinking what someone may or may not like because they expect something.
The title sounds very romantic. Is that what you’re saying?
If you listen (to the song) it sounds like I’m talking to a woman but I’m really talking to the woman which is music, who I’ve flirted with for 30 years. But now I’m willing to truly integrate (with it). I’ll date her in public and I’ll walk around with her and be seen, and I know that she loves me back.
And I thought it was a romantic song for Valentine’s Day.
Well, I’m lucky. I already have two songs that are big wedding songs. I have “Ordinary” which is off my first record, and “Beautiful,” the song that I did with Jim Brickman. Those are two good wedding songs. Now I’m hoping for three.
Is your daughter the young woman in the “Flirtin’ ” music video?
Yes. That’s my daughter dancing me at the end. She’s 16 and she does me proud every single day. Something that I hadn’t thought about until this trip — and I was telling my daughter about it — I did not think about how much family meant to me until I started coming to Hawaii. It wasn’t until I married into Mandie’s family, the Taketas, and I was exposed to a big extended family, and to the guy that I would call Dad — I call him Dad to this day — that I knew how good it is to have family. When I do anything — whether it’s “The Masked Singer,” whether it’s creating a song or a music video — my family is along with me, not just for the ride but actively participating. Mandie directed the video, Maile is dancing in it, and Mandie’s boyfriend, Jason, edited it together. We are definitely believers in ohana and so I try to let that show in my work.
Do you have a release date set for your EP?
We thought we had one but with the success of me even making a little bit of noise with the single, and the videos that I’d been dropping, people that I really respect and I like have been coming out of the woodwork to work with me because I put it out there. So I’m going to push (the release date) back so I can create with some of these people, but I’ll continue to drop singles.
