Ugly Sweater Says T-Pain Inspired Him to Give ‘Masked Singer’ a Shot: ‘I Saw That It Was Fun’

Spoiler alert: This story contains the identity of the contestant eliminated on Wednesday night’s (April 17) episode of The Masked Singer.

The 11th season of The Masked Singer has so far featured a very eclectic group of eliminated crooners, including comedian/actor Kevin Hart (Book); restauranteur Joe Bastianich (Spaghetti & Meatballs); TV personalities Savannah Chrisley (Afghan Hound), Billy Bush (Sir Lion) and Colton Underwood (Lovebird); as well as NFL hall of famer DeMarcus Ware (Koala) — and actual singer Sisqó (Lizard) too.

On Wednesday night (April 17), Ugly Sweater crushed it with some incomparable high notes on “Queen Night,” during a celebration of the iconic British rock group in the Group A finals. After wowing the judges in an earlier episode with a funk-forward cover of The Commodores’ “Brick House,” Sweater did it again with a sweet, soulful run through Queen’s 1984 power ballad “I Want to Break Free.”

When it came time to guess, the judges were in the neighborhood, with Robin Thicke praising the singer’s signature “nasty” notes on “House” (and quickly guessing the singer’s identity), while judge Rita Ora speculated it could be Smokey Robinson, Jenny McCarthy-Wahlberg guessed Aaron Neville (after earlier guessing that Lionel Richie covered his own song) and always-wrong Ken Jeong aiming too young with New Jack swinger Johnny Gill.

Who was that masked man who’s 13 Grammy nominations and has a lock as Billboard‘s top adult R&B male artist with the most No. 1s in that category to date? None other than former Gap Band lead singer and solo star Charlie Wilson, best known for such hits as “Party Train,” “You Dropped a Bomb on Me,” “Oops Upside Your Head” and his featured vocals on songs by rappers including Snoop Dogg, The Notorious B.I.G., Pharrell, U.G.K. and Tyler, the Creator, among many others.

In addition to his surprise appearance alongside Tyler at last weekend’s Coachella — where he performed on the rapper’s 2019 single “Earfquake” and did a bit of The Gap Band’s “Outstanding” — Wilson, 71, received a star on the Hollywood Walk of Fame in January and is currently promoting his Billboard top five adult R&B chart solo single “Superman.”

Billboard spoke with Wilson before his elimination to hear about how T-Pain inspired him to get in the Masked game, how wearing the Ugly Sweater was no holiday, and what it felt like to slip onto the main stage at Coachella last weekend.

Be honest: Had you ever watched this show before they reached out?

Oh yeah! I saw the one when T-Pain won [in season 1 as Monster]. I was so excited for him. I know T-Pain, he did songs for me and he’s a very gifted young man. I saw that it was fun and I wanted to get to be a part of it, but it just took some time because I was busy doing shows and recordings. I thought, “I can do this,” so it finally dropped in my lap.

Some iconic old-school and new-school R&B greats have appeared on the show — Bobby Brown, Faith Evans, Toni Braxton, Chaka Khan, Patti LaBelle, Seal, Gladys Knight — so it seems like there’s no shame in the game of putting on that costume right?

Yeah, my costume was… oh my gosh. It was built for me and was one of the most expensive suits they’ve built for the show. The [showrunners] kept telling me to try and make sure I stay as long as I can because [they said], “We spent a lot of money on this suit!” It was so heavy! So, so heavy I could barely walk in it. The feathers on the head were 8 to 10 pounds a piece and they had to take some off. I could barely pick up my feet!

It seems like a great showcase for so many of those classic R&B singers, especially some of your old-school peers.

I don’t know about anybody else, but I didn’t think about it being a showcase for me, because I’m still making No. 1 records. In fact, I have a top five song this week with one of my records [Wilson is in the top five on Billboard‘s Adult R&B Airplay chart with “Superman”]. I’m the only one out there still making top five records in the business!

You’ve been at this for more than 50 years, so tell me: Is this the weirdest gig you’ve ever had?

It’s a blessing and a curse at the same time, because a lot of people don’t want to see me have these records do as well as they’re doing. All those people you mentioned all wish they had the records I’m having. So yeah, I don’t pop my collar all the time, but people bring it up.

The judges’ guesses were all over the place, but mostly in the pocket. I can’t imagine you were ashamed to be confused for Smokey, Aaron or Lionel?

[Laughs] No, Robin Thicke said, “That’s Charlie Wilson!” as soon as I opened my mouth. I was like, “Oh man, I’m toast!” as soon as I opened my mouth and sang! He said, “I studied his voice and know him like the back of my hand.” I was like, “Could you just be quiet for a second?” He was tearing me up.

Speaking of, how did it feel to sing that Commodores song? Was there any rivalry with them in your bands’ heydays in the 1970s and ’80s?

Oh man, it was always that [rivalry] because if bands are good, they are gonna be at it. I won’t stand around and have someone call me a bootsy [someone who is uncool or weird]. I’m gonna get you. I’m gonna come after you like y’all coming after us! It was all in fun, not hostile, we was all in fun. I love The Commodores.

You’ve had so much success collaborating with rappers over the years — especially Snoop and Tyler. What is it about hip-hop that appeals to you? And talk to me about joining Tyler at Coachella last weekend.

It is great anytime I sing with these rappers or anyone from back in the day is coming for me and it’s their idea. If they want to do it, I’m gonna do it. I’m so, so blessed to have rappers still coming for me.

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