The Masked Singer Winner: Why Gretchen Wilson’s Victory Still Resonates

Honestly, if you told me twenty years ago that the "Redneck Woman" herself would be standing on a stage inside a giant, bejeweled Pearl costume while crying over a phone call from her daughter, I probably would’ve laughed. But that’s the magic of this show. Gretchen Wilson, the Season 13 winner of The Masked Singer, didn't just win a trophy; she basically reminded everyone that real talent doesn't have an expiration date.

It was a wild ride.

The season—officially dubbed "Lucky 13"—wrapped up in May 2025, and it felt like a fever dream in the best way possible. We had a Mad Scientist Monster, a disco-dancing Boogie Woogie, and a literal Pearl who sang like she was trying to tear the roof off the studio.

How Pearl Became the Winner of The Masked Singer

Most people thought the Pearl was someone like Shania Twain or maybe even Madonna early on. The guesses were all over the place. Ken Jeong, in his usual fashion, was convinced it was some legendary A-list actress, while Jenny McCarthy was leaning hard into the country music angle.

But when Pearl opened her mouth to sing "Black Horse and the Cherry Tree" by KT Tunstall, the grit in that voice was unmistakable. It wasn't just "good" singing. It was lived-in. It was raw.

Gretchen later admitted that being the "bejeweled princess" was the furthest thing from her actual personality. She’s a hoodie and sweatpants kind of person. Seeing her embrace the "gritty, unapologetic" nature of her character while wearing a costume that looked like it belonged in a high-end jewelry store was a masterclass in irony.

The Moments That Defined the Season 13 Finale

The finale wasn't a walk in the park. Gretchen had to face off against some seriously heavy hitters:

• Andy Grammer (Boogie Woogie): The runner-up who turned every performance into a massive party.
• Meg Donnelly (Coral): The Disney star who surprised everyone with her theatrical range.
• Brian Kelley (Mad Scientist Monster): Half of Florida Georgia Line, who brought that smooth Nashville vibe.

The turning point was definitely the "special telephone call" twist. When Gretchen heard her daughter’s voice on the line, the "tough exterior" she talked about in her clue packages just evaporated. You could hear the crack in her voice. That’s the stuff that makes people vote.

👉 See also: The Summer I Turned Pretty Ages: Why the Timeline Changes Everything

She eventually sealed the deal with a cover of "I'll Stand By You" by The Pretenders. It was simple. It was emotional. It made the Golden Mask Trophy feel like it actually belonged to her.

What Most People Get Wrong About the Winners

There’s this weird misconception that only "washed up" stars go on this show. That's just wrong. Look at the history.

Before Gretchen, we had Boyz II Men winning Season 12 as the Buffalos. They were the first group to ever win the US version, and they are literal R&B royalty. Then you’ve got Vanessa Hudgens (Season 11) and Ne-Yo (Season 10). These aren't people looking for a comeback; they’re people who want to prove they can still command a stage without their "brand" getting in the way.

Gretchen Wilson mentioned that her "hard edge" had actually stood in the way of her success at times. People put her in a box. Being the winner of The Masked Singer allowed her to step out of that box—even if she was technically stepping into a giant shell.

Why Season 14 Is Changing the Game

As we move into 2026, the show is currently in the middle of Season 14, and the vibe has shifted. We've already seen some massive unmaskings, like Tiffany Haddish as Le Who Who and David Ortiz (Big Papi!) as Googly Eyes.

The producers are leaning heavily into "Fear Night" and "Ozzy Osbourne Tributes," making the path to the trophy even harder. If you’re watching the current season, keep an eye on Cat Witch and Galaxy Girl. The internet is already convinced they have what it takes to join the winner's circle.

Actionable Insights for Fans and Aspiring Sleuths

If you’re trying to predict the next champion, stop looking at the height of the celebrity. That’s a rookie mistake. Instead, focus on these three things that almost every winner, including Gretchen Wilson, had in common:

1. Vocal Consistency Over Gimmicks: The winners almost always choose songs that show off a "signature" rasp or range that the panel can eventually identify.
2. The Emotional Narrative: If a contestant starts talking about being "misunderstood" or wanting to "find themselves again," they are being positioned for a deep run.
3. Song Diversity: Gretchen went from Dolly Parton to Blue Öyster Cult. If a singer stays in one genre, they usually get bored—and the audience does, too.

The reality is that The Masked Singer has become a weirdly legitimate venue for vocalists to strip away the baggage of their fame. Whether you're a country icon or a boy band legend, the mask leveled the playing field. Gretchen Wilson proved that even a "Redneck Woman" can be a Pearl if you give her the right mic and a bit of anonymity.

Keep your ears open for the Season 14 finale coming later this spring. The competition is getting tighter, and the "Fear Night" survivors are looking stronger than ever.