Emily Zemler
View all posts by Emily Zemler April 2, 2026
Ashlee Simpson FOX; Paul Archuleta/Getty Images In a surprise reveal, Ashlee Simpson was named as the winner of the 14th season of The Masked Singer. The pop star, whose was dressed as “Galaxy Girl” during the competition series, performed Olivia Rodrigo’s “Good 4 U” and P!nk’s “Try” before winning the trophy.
Simpson’s sister Jessica Simpson was on hand for the big reveal, helping her to remove her giant mask. Simpson admitted, “Honestly, I’m kind of freaking out right now. I’ve literally had the best experience of my life here… I have grown so much here and I can’t even believe I won.”
The singer was notably competing against her own husband, Evan Ross, who performed as the “Stingray.” She told Billboard, “Going into the show, I didn’t think I was going to be on that long, and all of a sudden I got competitive — not against my husband, because I couldn’t see him… We were both just rooting each other on and there to have a good time. I definitely got into the competition not knowing, “Oh yeah, I’m really going to work on this song and get there!”
Simpson also told Billboard that she aimed to showcase songs by female singers during her time on the show, including Rodrigo, Paramore, and Chappell Roan. “We were looking for female artists and girls that had that strong quality,” she noted. “I really wanted that for Galaxy Girl, who is strong, sensitive and there to have a good time.”
Simpson’s last album, Bittersweet World, was released in 2008. In 2019, she and Ross shared a meditative love ballad, “Phases.” The singer also recently performed in Las Vegas as part of a short residency at Voltaire at the Venetian Resort, but has generally stayed out of the spotlight.
