Ashlee Simpson Ross overcame a very public and embarrassing moment on television early in her career by reinventing herself on a singing competition. She wore a unique, space-themed mask and delivered powerful vocal performances, winning over viewers once again.
Let’s not dwell on the 2004 “Saturday Night Live” mishap where she was caught lip-syncing. It was awkward – she did a strange dance and quickly left the stage, and her father tried to explain it away. But that happened a long time ago.
The winner of “The Masked Singer,” who is married to Evan Ross (son of Diana Ross), was overjoyed after her win, sharing her excitement in an interview released Wednesday night. During the finale, she performed Olivia Rodrigo’s hit song, “Good 4 U.”
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Twenty years after her first, groundbreaking album came out, the singer – who also became a star on reality television – is getting ready to perform a long-term show at the Venetian resort in Las Vegas.
Simpson described her experience as transformative, saying she fully embraced the role of Galaxy Girl and loved working with her team. She enjoyed the challenge of performing while hidden from the audience, finding it a fresh and exciting way to connect with the performance. It was a truly unique and revealing experience for her.
I remember fall 2004 so well! Jessica Simpson was really having a moment. She was getting ready for her second appearance as the musical guest on ‘Saturday Night Live,’ and her reality show with Nick Lachey, documenting their new marriage, was becoming super popular. Plus, she’d just dropped an album that ended up being the best-selling one of the year by a female artist – it was a big time for her!
As the band began to play, the wrong lyrics unexpectedly filled the speakers. It wasn’t Simpson singing them, so she awkwardly danced for a moment before leaving the stage and stopping the performance. The broadcast then cut to a commercial break.
Lorne Michaels would confirm later that it had been a first for the sketch show.
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It was “Saturday Night,” but it sure didn’t sound “Live.”
It was classic live TV, as Jude Law himself said during the show’s closing moments! Honestly, it was a bit of a mess. While Jude was trying to wrap things up, Paloma Simpson just started talking a mile a minute, and unfortunately, she ended up blaming the band for everything. It didn’t really make a lot of sense, but it was certainly a memorable way to end the night – and not in a good way, poor band!
“I was so embarrassed,” she explained. “We started playing the wrong song, and I panicked, so I just started improvising with a little hoedown. I really apologize!”
A year earlier, Ashlee Simpson’s sister had famously asked silly questions on television – like whether Chicken of the Sea was actually chicken, and if buffalo wings came from buffalo. People remembered those moments more than anything else. When Ashlee Simpson clearly pretended to sing live, many viewers assumed she couldn’t sing at all, and she quickly became the subject of ridicule.
Afterward, her dad explained that acid reflux had irritated her vocal cords, forcing her to switch from singing live to using a pre-recorded track at the last minute. He considered it a valuable lesson and expressed confidence she would shine in future performances.
Joe Simpson explained to Ryan Seacrest in a radio interview that his daughter, like many performers, uses pre-recorded backing tracks during performances. He mentioned this happened to them on Saturday, and it helps ensure a polished vocal performance on television.
He mentioned she hadn’t used vocal tracks previously, but added that sometimes you just have to do what’s necessary.
Music
Jessica Simpson’s new memoir, “Open Book,” reveals deeply personal details about her life, including experiences with sexual abuse, struggles with addiction, and her relationship with John Mayer.
Several months after that, her performance at the 2005 Orange Bowl halftime show was widely criticized, even drawing boos on national television. Many people said it was an even more negative reaction than her appearance on “Saturday Night Live.”
Her career continued, though it wasn’t without its challenges. After releasing a few more albums, she tried her hand at Broadway, and eventually returned to acting. She often talked about making music again, but other commitments kept interfering.
In 2025, following a small celebratory performance in West Hollywood the previous year marking two decades since her first successful album, she began a residency at the Venetian in Las Vegas. The show was so well-received that it continued into 2026.
Throughout her time on “The Masked Singer,” Jessica Simpson showed everyone that she’s a talented singer with strong vocal skills. She even outperformed her husband, who appeared as Stingray and was eliminated earlier in the season.
I truly love performing, and getting back on stage feels wonderful,” she shared with People. “It’s inspiring me to continue making music and playing shows. Experiences like ‘The Masked Singer’ and my Vegas performances, and upcoming events like Pride and Stagecoach, remind me that this is my passion.
“I’m happy to be doing it again.”
Good for you, Galaxy Girl.
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2026-04-03 01:01