Gretchen Wilson didn’t expect to win 'The Masked Singer' — and felt bad about beating one contestant

Winner of season 13 'The Masked Singer' said she 'felt bad' after winning. And reason will surprise you.
PUBLISHED MAY 12, 2025
Screenshot of Gretchen Wilson, winner of season 13 from 'The Masked Singer'(Cover Image Source: YouTube | From 'The Masked Singer’)
Screenshot of Gretchen Wilson, winner of season 13 from 'The Masked Singer'(Cover Image Source: YouTube | From 'The Masked Singer’)

Gretchen Wilson, who was revealed as the winning celebrity under the costume of Pearl on 'The Masked Singer,' did not make her way back easily on the stage. The 51-year-old singer shared during her winning moment, "I have had a rough couple of years." She explained, "I was injured and in a wheelchair, and I thought I could not ever do anything like this." She added, "But I worked hard, I prayed hard, and I got so far, but the opportunity of being on the show only proved to me that there is absolutely nothing I can't do."



 

According to Variety, the country singer had been in an accident that left both her leg bones and ankle shattered. "I was in a wheelchair for about eight months,” she said. “And I was only a year out of the walking boot when I agreed to do the show." She also told the outlet, "It was a real chance for me to be able to prove to myself whether I’ve still got it. If I should be thinking about the next 10 years professionally or the next 10 years in retirement?”



 

However, things took an interesting turn when, following her win, the 'Redneck Women' singer on May 9 made a shocking revelation in an interview with People. Wilson shared she was shocked when host Nick Cannon announced her as the winner. "I was positive that Boogie Woogie (who was revealed as Andy Grammer) won. I thought he was just the most amazing singer. In my head, he had won it weeks before. I was so stunned because I had myself ready to hear that I was in second place. I was so ready for it; I had already decided that that's what it should be in my head."



 

She added, "But being a mom, I felt bad." Feeling torn with the reveal, she continued, "It was like, ‘No, no, no, no, no, no, I'm happy with second! He won!" She anticipated "that's probably how he (Andy Grammer AKA Boogie Woogie) would've felt, too. He's just such an incredibly, incredibly likable person. I wish I could have shared it with him." Nonetheless, Wilson gracefully accepted the golden trophy. admitting that it was a mark of a new chapter in her life. "I feel like it's sort of a comeback moment,” she said, before adding, “I'm ready to take on anything.”



 

When asked what made her participate in the show, Wilson replied to the aforementioned outlet that, "I loved the chance at being Pearl." Noting that she makes a clear distinction between the two identities, she added. "When I see Pearl, I don't see Gretchen; I just see Ms. Pearl. But I'm starting to realize that that is me; that's just a different part of me that I don't often show or share." Uncertain about what lies ahead in life after her success on the show, Wilson said, "I don't know. I have no idea what life's going to bring, what challenges, what rewards, or what craziness might come. What I do know is that I have completed these last two things. This one, especially, what I went through, the challenges that I faced, I feel like I can take almost anything on. Whether it's familiar or unfamiliar, let's just see how it goes at this moment."

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