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Ashlee Simpson Is Definitely Not Living in the ~Shadow~ Anymore — See Her Epic Transformation

Fashion & Beauty

Oct 3, 2019 9:00 am·

By Jaclyn Roth

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Are you still as obsessed with “Pieces of Me” as we are? Well, good! Ashlee Simpson entered the scene in 2002 and has been a household name ever since. The blonde beauty was one of Jessica Simpson’s back-up dancers on tour, and then she went on to score her own reality series called The Ashlee Simpson Show on MTV in 2004. The 35-year-old wanted to show everyone that she was a little bit spunkier and sassier than her older sister.

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These days, Ashlee is married to Evan Ross, and they share one child together — she has another kid with her ex Pete Wentz — and she seems like she is in a great spot in her life. The duo just put out an EP in October and are now focusing on their respective careers. We hope she makes another bop sometime soon!

Scroll through the gallery below to see Ashlee’s amazing transformation over the years.

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Tiny Dancer

Ashlee first started out as Jessica’s back-up dancer following the success of her 1999 album called Sweet Kisses. The entertainer started studying classical ballet at just 3 three years old, and she enrolled at the School of American Ballet in New York City when she was 11 years old.

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TV Star

The starlet made her first major screen debut in 2003 starring on 7th Heaven as Cecilia Smith. “I had that fringe bang going on the whole time,” she told InStyle of her look. “I like a bang, but now, I just get bangs from breaking my hair.”

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All Black

The singer rocked dark hair on the red carpet in 2004. “So, that was the first time I went for something different,” she explained to InStyle about her dramatic new ‘do. “I rebelled and bought a box of hair dye. I had wanted to go black. With that album [Autobiography], it was just where I was at, like, ‘Yeah! I’m feisty!’”

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Reality TV Babe

Following the success of Jessica’s show with her then-husband, Nick Lachey, called Newlyweds: Nick and Jessica, it was revealed that Ashlee was getting her own series, The Ashlee Simpson Show. Ashlee wanted the show to focus on her new album.

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Love Is in the Air

While filming the show, Ashlee appeared in Ryan Cabrera’s music video his song called “On the Way Down,” and later on, Ryan, 37, was Ashlee’s love interest on the MTV hit show. The handsome hunk even inspired some of Ashlee’s songs off her first album.

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Real Life

“Ashlee’s show was 100 percent real,” Ryan said in 2016. “They just followed us around. TV shows at that time were completely different. They literally just followed you around with a camera, and whatever happened, happened.”

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Woops!

In October 2004, the TV personality appeared as a musical guest on Saturday Night Live to promote her album, but sadly, it was revealed that she had lip-synched the performance. “It’s definitely not difficult to talk about,” she told E! News in 2018 about the incident. “That was a very long time ago. It’s something that happened to me and things in life happen, and they make you stronger. They make you a better performer and a better person. I think things like that build your character and your strength, and it’s how you handle them [that matters].”

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Making Music

A year later, the mom of two released her second album, I Am Me, which featured hit songs including “Boyfriend” and “L.O.V.E.”

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Changes

In April 2006, Ashlee revealed that she had gotten a nose job. “I don’t get bothered by people saying what they say,” she told Harper’s BAZAAR at the time. “I’m a happy person, and I’m happy with my looks. I loved how I looked. I’m not an insecure person, nor was I before.” Ashlee’s dad, Joe Simpson, explained that there was a problem with how she was breathing and needed the surgery.

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New Bling

Ashlee met Pete at the MTV VMAs in 2006, but they didn’t actually confirm their relationship for quite a bit of time. In February 2008, Ashlee was spotted with a diamond ring on her finger, and two months later, they revealed they were engaged.

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A Musical Match

“Maybe in a different universe, we’d be some hot couple, but not in this one,” the rocker, 40, told Rolling Stone about their relationship. “I’m attracted to creative people and train wrecks, and there’s no shortage of that in Los Angeles.”

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Broadway Babe

After the Texas native performed as Roxie Hart in the musical production of Chicago, she began working on her third studio album, but it didn’t perform as well as her previous ones did.

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Happy Times

Two weeks after her wedding to Pete, Ashlee announced she was pregnant. “While many have speculated about this, we wanted to wait until after the first trimester to officially confirm that we are expecting our first child,” she said. “This is truly the most joyous time in our lives, and we are excited to share the happy news and start our family.” In November 2008, the former flames welcomed their son, Bronx Mowgli, into the world.

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Not Meant to Be

However, there was trouble in paradise as Ashlee and Pete called it quits in 2011. The Fall Out Boy frontman revealed after his band went on hiatus in 2010 is when things started to unravel. “At 31, we’d had all these great years as a band, and then we took time off, and I basically became Mr. Mom,” he told Howard Stern in 2015. “I had the beard, the flannel shirt. I didn’t know what my identity was. That factored in. When your identity is what you do, it’s hard when you stop doing it.”

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Onto the Next

Following her split, Ashlee went on to date actor Vincent Piazza for a year and a half.

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Making Moves

In 2012, the “Shadow” crooner released her single “Bat for a Heart” and described her fourth studio album as having a “folk feel.”

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Meet Cute

Ashlee moved on with Evan — her now husband — in 2013. “We met at my friend’s birthday party. Evan walked in, and he was really cute,” she recalled on their E! show, Ashlee+Evan. “We made out, and then I left. You definitely had a young, fun, bad boy side about you. When we actually got together, you really shocked me and impressed me.”

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New Addition

In January 2014, Ashlee announced she was engaged to The Hunger Games actor. They got married in August 2014, at Diana Ross’ estate in Connecticut. In July 2015, Ashlee gave birth to her second child — her first with Evan — and they named her Jagger Snow Ross.

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The Big Return

Ashlee and Evan took some time off to be with their family, but they returned with their E! show in September 2018. However, Ashlee never thought she would be back on the small screen again. “But that’s also the fun thing — catching up with me all these years. I’ve been a mom and loving every second of that,” she told Us Weekly at the time.

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Round 2

“We’re doing it in a real different way [than The Ashlee Simpson Show],” Evan, 31, said. “It’s a lot more documentary than a reality [show], the way we shot it at least. It was something that we created that we ended up pitching. It wasn’t something that was given to us. It was something that we executive produced, decided what we were really trying to do and go behind it.”

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Coparenting at Its Finest

Also, it’s not awkward for Ashlee to see her ex Pete all the time. “It could go all different ways,” Evan told the outlet. “I think the fact that there is a lot of respect amongst all of us. That makes it easier. And we’re all really close friends. It’s easy, we got really lucky with that.”

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Bring on the Babies

So, will there be more kids in the future for Evan and Ashlee? Sounds like it! “I would love to [have more],” Evan said in August. “That’s the plan, but you know, we have to see. I want a flock, but it’s up to her!”

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Next Chapter

Unfortunately, Ashlee and Evan decided to take a step away from the cameras for now. “We are not doing it anymore,” she said this month. “We had so much fun doing it, but we’re both working on our own projects, and we’re literally there with each other every day.”

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