Jessica Simpson Reacts to Sister Ashlee Simpson Winning Masked Singer

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Ashlee Simpson took everyone’s breath away on The Masked Singer.

That also includes her sister, Jessica Simpson. When the singer of “Pieces of Me” won season 14 of the competition, Jessica was quick to offer her congratulations and praise.

Oh my gosh, watching her on the finale was everything! I was glued to my couch, of course, but it felt like she was performing just for me the whole time, like she always does. Seriously, she’s constantly giving us amazing performances, so she absolutely deserved that stage, and I was SO happy the judges and everyone else finally got to see what I’ve known all along!

Ashlee, 41, was surprised to win, but Jessica, 45, who revealed her sister’s identity as Galaxy Girl, wasn’t at all surprised by the outcome, saying, “I totally expected it!”

The “Take My Breath Away” singer proved that she’ll always be rooting for Ashlee.

“Always her number one fan,” she declared. “She can do everything.”

Ashlee Simpson, mother to Jagger (10) and Ziggy (5) with husband Evan Ross, and also to Bronx (17) from a previous relationship with Pete Wentz, recently shared what winning felt like.

I’m really overwhelmed right now,” she said. “This has been the best experience of my life. I’ve learned and grown so much, and it’s taught me that things aren’t always as easy as they look – it takes a lot of hard work.”

It was also exciting to see Evan compete as Stingray, even though he was eliminated in week 10 on March 18th.

She remembered they were competing, and it was strange because they couldn’t see each other during the competition.

Winning The Masked Singer felt particularly meaningful for the singer of “Lala,” as it helped overcome the negative impact of a well-known 2004 incident on Saturday Night Live where she was criticized for lip-syncing. This event had affected her career for many years.

I’ve wanted to be on The Masked Singer for years, and being in the finale has been even more incredible than I expected,” she shared in a video before her win. “It takes courage to be vulnerable and perform. When I was younger, I was fearless and felt like I could do anything—but then a single event changed my perspective.

She explained that the public shaming was incredibly painful. Being called a fraud and an imposter felt devastating, especially because she was so young and feared it would ruin her life. After that experience, she became much more careful and avoided taking chances.

Performing as Galaxy Girl showed her she could achieve far more than she thought possible.

She explained that she’s rediscovered the confident performer she used to be and has finally moved on from her past. Winning the Golden Mask award, she hopes, would demonstrate to her children the value of taking chances and prove that she’s always been someone to admire.

Keep reading to see all the celebs who rocked out this season on The Masked Singer.

Baseball superstar David Ortiz, known as ‘Big Papi,’ was unmasked as the tallest contestant on the season 14 premiere of The Masked Singer and was eliminated.

During the first episode of the show, the costumed duo known as The Croissants were revealed to be reality TV stars Julie and Todd Chrisley.

The performer who had the audience roaring with laughter was revealed to be comedian Tiffany Haddish, and she was unfortunately eliminated during the second week of the competition.

That signature voice could only belong to one man: “Funky Cold Medina” rapper Tone Loc.

Everyone was surprised when the performer dressed as the Scarab took their final bow and was unmasked as Taraji P. Henson, the Empire star and Academy Award nominee.

Everyone was shocked when Queen Corgi unexpectedly left the competition right before the big reveal, and was unmasked as comedian and podcast host Claudia Oshry.

The masked singer Calla Lily revealed herself to be Teddi Mellencamp, a former cast member of The Real Housewives of Beverly Hills. She shared that she was diagnosed with multiple brain tumors in 2025, making her emotional exit particularly poignant.

I was absolutely gutted when The Owl was unmasked! It turned out to be Billy Ray Cyrus, and you could just feel how disappointed he was to be eliminated. Honestly, it seemed like it really broke his heart – poor guy!

Reality TV star Heidi Montag, known from The Hills, was revealed to be the Snow Cone contestant on February 25th in a tearful elimination from the show.

The man behind the aubergine was none other than Melrose Place alum Jack Wagner.

Despite a disguise that included a soccer ball for a head, the judges didn’t realize that retired soccer player and former L.A. Galaxy defender Alexi Lalas was the one performing as the High Voltage character.

TV Judge Greg Mathis was unmasked as the Golden Veggie on the show, and he was eliminated during a double elimination on Star Trek night, March 18th.

Also sent packing week 10 was Diana Ross‘ son Evan Ross.

Pangolin’s run on The Masked Singer concluded in week eleven when Rachel Platten, the singer of “Fight Song,” was eliminated during the semi-final round.

Normani, who first gained fame as a finalist on The X Factor and as a member of Fifth Harmony, impressed audiences with her strong vocals as the Crane on the show, ultimately finishing in fourth place.

As a lifestyle expert, I’m always fascinated by incredible reveals! Recently, Kylie Cantrall from Descendants had a truly amazing moment. She was the performer behind the Cat Witch mask at the start of season 14, and she managed to keep her identity a secret from the judges the entire time – talk about a performance and a secret well kept! It was a really fun surprise for the fans.

Cantrall narrowly missed winning, finishing in third place at the April 1st competition.

Phillip Phillips, who previously won American Idol, almost won another singing competition, but finished as the runner-up in season 14.

And the winner is…

Ashlee Simpson is your new Masked Singer champ!

The “Pieces of Me” singer beat out over a dozen celebrities to take home the season 14 title.

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2026-04-02 16:52