‘The Masked Singer’ Winner: Pearl Reveals Concerns & Challenges of Performances

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[Warning: The below contains MAJOR spoilers for The Masked Singer Season 13 finale.]

A country music singer now has another trophy to add to her many awards.

The Masked Singer Season 13 finale saw Boogie Woogie, Coral, Mad Scientist, and Pearl compete to emerge the winner, and it was ultimately Pearl who did so. Under the mask was singer-songwriter Gretchen Wilson. (Andy Grammer‘s Boogie Woogie was second, Meg Donnelly‘s Coral third, and Brian Kelley‘s Mad Scientist fourth.) Below, she opens up about winning and her time on the show.

Right after it was announced on the show that you won, you said you were floored. How does it feel now that you’ve had some time to sit with it and you’re looking back on the entire season?

Gretchen Wilson: Well, actually right now, today, what’s most exciting is that I get to talk about it finally. I mean, this is such a hard thing, especially when you’ve gone through every show, when you make it all the way to the end and you don’t get to say anything. There’s just a few tiny little group of people that actually know what’s going on and they wouldn’t have known but the show actually involved them with some of their clues and stuff, and so that’s how we got there. But I’m super excited to just share it with people. For people that know me and have known me my whole life to go, you did what?! Because it’s so far outside of my norm and what I would normally do. But it was a great experience and looking back on it, I’m so glad I did it. I’m so glad that I challenged myself to do something that I wasn’t sure about, and I’m really excited just to see what everyone’s thoughts are going to be on it.

Michael Becker / Fox

Speaking of challenging yourself, what made you say yes to doing the show? Did you have any hesitations when they first reached out?

Yes, and they reached out several times, and I wasn’t in a place in my life where I thought this was something that fit what my normal character would be. Then this last time when they reached out, I had gone through some things, some personal medical things, and I was trying to see if I had, for me, what it took to actually get back out there and do this whole thing. I had some post covid stuff, breathing, high blood pressure that took me a while to get under control. So that was a challenge that I had to sort of ease back into going back out on the road.

But the biggest concern for me was the choreography and the dancing because I also broke my leg severely a couple of years ago, and I wasn’t sure about all the dancing, the heels. It is kind of a lot. So, for me it was like, okay, I’ve gone through it all. I’m healthy now, I’m better, I’ve gotten the weight back off, but can I still do this? Because it had been a few years, and so it was, like, the best challenge ever for me to prove to myself to go out there, to be in that costume, to sweat like that, to have the extra weight, to learn the moves, and then to bring the voice every night. It was a challenge for me personally and something that I’m so actually proud of myself for doing.

What went into your song choices, especially for the finale?

I believe that there’s only a certain number of songs that you have access to. I felt like I had a great variety of things to choose from, and I was thinking to myself at the time that some of the other contestants may not have thought so, because I’m thinking I’m the oldest lady on the show. That’s the way I was thinking. These young girls are having to look at songs from The Pretenders and The Outfield, and they’re like, who? But for me, I was looking at it like, oh, songs that I know, really good old classic rock songs and good songs from the ‘80s and stuff that I grew up on as a kid. I loved my choices. As a matter of fact, I could have chosen probably 10 others. It was just we only had enough time for so many.

Which performance made you think you could win or at least make it far?

I would have to say that I was unsure until I got to “Conga,” until I got to Gloria Estefan and the Miami Sound Machine. And even though there wasn’t anything really vocally acrobatic in that song, it is not an easy song to sing. It moves very fast, and I feel like if I hadn’t had some time as a child living in South Miami and Dade County and growing up around — a lot of my friends were all Puerto Ricans and Cubans, and so they speak really, really, really fast all the time, very fast talking, and I think that that sort of set me up and helped me. I actually saw Gloria Estefan and Miami Sound Machine perform in Miami when I was a child. I think it was just still the Miami Sound Machine. So I’ve loved that song for a long time.

You had incredible performances. Is that the one that you’re most proud of?

I actually haven’t seen them all yet as we’re talking, so I can’t actually — up ‘til now, yes. But as you know, I’ll see the last of it tonight. I think it may actually be one of the ones tonight, but I haven’t seen it or heard it yet, so I’m not sure. But as of right now, yeah, I would say that “Conga” is my favorite.

Talk about the panelists’ guesses because Robin Thicke did figure you out.

It took him a minute. It took him a minute, but he finally did get there and I knew he would. There was something in me every time I stood out there that was like, “He’s going to get it. One of these times, he’s going to get it because he’s all around it. He’s all over it.” I could see that he was really working it in his mind. He was working it to death, trying to figure it out. I think one of the things that I did that not a lot of people did do was bring so many different voices, and that’s just me growing up as a bar band singer. I mean, for years people would tell me, “Oh, you’re so good because you sound just like… You’re so good, you sound just like Ann Wilson when you sing ‘Heart,'” or “You’re so good, you sound just like Melissa Etheridge.” So I have that. That’s kind of how I honed my entire career in, was just by sounding like other people. So that was an advantage, I think, to me. But yeah, I mean, I couldn’t have been more stunned by the names that they were dropping out there because I was like, I don’t mind being compared to any of them. Half of those women are heroes of mine.

So had you come into this expecting, if anyone was going to figure you out, it would be Robin or one of the other panelists?

I didn’t really actually expect anybody would figure me out. I thought anybody who’s close to me, friends and family, artists that I’m close to, like my brothers in the MuzikMafia, Big and Rich, these guys are going to instantly — I thought the first word, they’re going to know who I am, and they really didn’t. They started to figure it out as the season went on, but it took a while for everybody. I didn’t think anybody on the panel was going to guess.

What are you going to take away from the entire experience?

I think the biggest thing that I’m going to take away from this is knowing that it’s okay for me professionally and maybe even personally, too, to step outside of my norm, of my comfort zone, to kind of flirt around with being a little different from time to time, and just knowing that I don’t have to just be this straightforward redneck woman with the bottle of whiskey riding a four wheeler. I can sometimes be Pearl, and people like Pearl, too.

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What surprised you the most about being on the show besides the secrecy of it?

I think I was really surprised by the talent, the talent that they continue year after year, season after season to continue to bring in, and just when you think that they are going to run out of talented people, they surprise you with someone else. I’m really shocked at how well everybody else can sing, even people that aren’t in the — they go in there, they work hard. There’s a vocal coach available to you if you’re not typically a singer, that’ll help you just work on your song and get your stuff together. But man, they work hard because a lot of these people — I know how hard it was for me, and this is what I do for a living, so imagine being a boxer or a swimmer or a basketball player or some of the other talent that they get in there, and how hard they have to work to get a really great vocal by the time that the performance comes out. So I’m really blown away with how hard even the non-singers work to sing and how well they sound.

I think I see the trophy in the background?

Yes, I’ll grab it.

That is cool.

It’s the biggest one. I’ve got all these — I’ve got a Grammy and a couple of CMAs, but this is the biggest. It’s huge, and it has my name on the back. And this is crazy, but when I was setting them all up there yesterday in preparation for this, I counted them, and Season 13, 13th trophy. It’s number 13.