It was a night of dazzling lights, emotional reveals, and a first-of-its-kind twist as "The Masked Singer" wrapped its fourteenth season on April 1, 2026. The grand finale brought together four costumed celebrities—Galaxy Girl, Pugcasso, Crane, and Cat Witch—each vying for the coveted Golden Mask Trophy. But as confetti rained down and masks came off, it was Ashlee Simpson, hidden behind the persona of Galaxy Girl, who emerged victorious. The surprise didn’t end there: her husband, Evan Ross, had also competed this season as Stingray, making them the first married couple to compete separately, not as a duo, in the show’s history.
The finale, broadcast live, was a star-studded affair from the outset. Panelist Ken Jeong kicked off the evening with a spirited performance of "Mystical Magical" by Benson Boone, joined onstage by the four finalists. Host Nick Cannon set the stakes high, reminding viewers that the remaining contestants had collectively sold over 28 million albums, with nine gold and ten platinum singles among them. As the stage glittered and the audience buzzed, the night promised both spectacle and suspense—and it delivered on both counts.
Each finalist brought their own story and style to their last performances. Galaxy Girl, whose clues hinted at a journey from public humiliation to renewed confidence, delivered a powerful rendition of Olivia Rodrigo’s "Good 4 U." Cat Witch, reflecting on her dreams and the thrill of seeing fans dress as her for Halloween, wowed the crowd with JoJo’s "Leave (Get Out)." Pugcasso, embracing his identity as a dad and seasoned musician, tugged at heartstrings with Cyndi Lauper’s "True Colors." Crane, meanwhile, spoke of healing and reconnection, belting out Janet Jackson’s "Together Again" in a performance that had many convinced her true identity was Normani from Fifth Harmony.
As the judges—Robin Thicke, Rita Ora, Jenny McCarthy, and Ken Jeong—debated and reminisced over their season-long guesses, the first elimination loomed. The audience and panel cast their votes, and Crane was the first to be unmasked. In a heartfelt moment, her close friend Khalid appeared onstage to help unveil her identity. Sure enough, under the mask was Normani, confirming the suspicions of several judges. As Khalid noted, "It’s not easy winning all these awards, but luckily, Crane had some help doing it," referencing Normani’s impressive list of accolades.
After a brief pause for a presidential address (the show’s live nature meant the action paused and resumed in real time), the remaining three contestants prepared for their final shot at the title. Galaxy Girl soared with Pink’s "Try," Cat Witch dazzled with Tate McRae’s "Greedy," and Pugcasso rocked out to Phil Collins’ "Sussudio." For the first time, the show dropped the voice modulators, letting the real voices of the stars shine through. The clues—and the voices—made it clear to many that Galaxy Girl was Ashlee Simpson, Cat Witch was Kylie Cantrall, and Pugcasso remained a mystery to most, even as he gave his all on stage.
When the next round of votes was tallied, Cat Witch was revealed as the third-place finisher. Her big clue came via a video from Meg Donnelly, a past finalist, and a mousetrap—"I’ve never been afraid of a mouse. In fact, one helped launch my whole career," Kylie Cantrall teased before removing her mask. As the judges made their final guesses, Rita Ora nailed it: "Kylie Cantrall!"
The tension mounted as only two contestants remained: Pugcasso and Galaxy Girl. In a dramatic final reveal, Nick Cannon announced Galaxy Girl as the winner of season 14. Pugcasso, the runner-up, received a video message from his friend Randy Jackson, who referenced a "golden ticket" and the "golden opportunity that started it all." The judges’ guesses ranged from Justin Guarini to Kris Allen, but when the mask came off, it was "American Idol" winner Phillip Phillips smiling back at them.
Now, all eyes were on Galaxy Girl. The final clue—a book titled "All About Me" delivered by her sister Jessica Simpson—sealed the deal for the judges, who unanimously guessed Ashlee Simpson. With a flourish, the mask came off, and the winner was revealed: it was indeed Ashlee Simpson, radiant and triumphant. The season had started with a bang, but ended with a family affair: Ashlee’s husband, Evan Ross, had been unmasked earlier in the season as Stingray, making them the first married couple to compete separately on the show.
In an interview with Parade following her win, Simpson shared insights into the secretive and surreal experience. "They approached us separately and both of us were into this idea and we were both like, ‘Let’s do it!'" she explained. The couple, who are parents to Jagger Snow, 10, and Ziggy Blu, 5, kept their participation under wraps—even from their children. "It was definitely like an NDA with our children," Simpson joked, but admitted the kids eventually caught on from overhearing rehearsals. The elaborate production protocols—masks, gloves, and sweatshirts emblazoned with "Don’t talk to me"—ensured the couple never crossed paths on set. "If they ever knew it was us, they’d pass us so fast. So I never saw him on set or anything," she recalled, adding a laugh about recognizing Evan’s baggy pants from afar.
Simpson described the experience as both nerve-wracking and exhilarating. "Every episode that you’re doing the show, you’re like, I don’t know when my mask is coming off. It’s like an insane feeling," she said. The element of surprise kept her on her toes, but also made the journey more memorable. She singled out her first performance—"Super Graphic Ultra Modern Girl" by Chappell Roan—and her finale numbers, "Good 4 U" and "Try," as personal highlights. "I loved the last performance, like trying to get to go up in the sky like that. That was amazing… that felt powerful and fun," she said.
Beyond the trophy, the show reignited Simpson’s creative spark. "I’m inspired. I have the bug back and it just felt good to perform. I feel like it’s my happy place," she told Parade. Fans won’t have to wait long to see what’s next: Simpson is slated to perform at the Stagecoach music festival (April 24-26, 2026) and the OUTLOUD music festival in West Hollywood for Pride Month (June 5-7, 2026). She promised, "Definitely new music to come … I am excited to keep going."
For Ashlee Simpson, "The Masked Singer" was more than just a competition; it was a family adventure, a career revival, and a testament to the show’s enduring ability to surprise. As the curtain fell on season 14, fans were left not only with a new champion, but with the promise of more music and more memories from a singer who rediscovered her voice—both behind the mask and beyond it.