In 2004, Ashlee Simpson shot to worldwide fame. Then for almost a decade, she disappeared.

On October 23, 2004, Ashlee Simpson stepped onto the legendary Saturday Night Live stage to perform her single 'Pieces of Me'.

It should have been a major highlight in her career. But instead, it marked the beginning of her downfall.

When Ashlee began to perform 'Autobiography' as her second song of the performance, the vocals for 'Pieces of Me' began playing in the background, exposing the singer for lip-syncing her performance.

As her band continued to play in the background, Ashlee awkwardly stood completely frozen. Finally, after breaking out into a bizarre country-style dance, the singer, who was just 20 years old at the time, walked off the stage.

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In the weeks that followed, the singer was hit with constant backlash, leading Ashlee to claim that she had acid reflux meaning she couldn't sing live.

Although Ashlee's singing career continued for several years after the incident, she eventually faded from the spotlight.


In 2018, after almost a decade of maintaining a low-profile, Ashlee returned to the spotlight with a new reality show – Ashlee + Evan – which documented her life with her husband Evan Ross, who is an actor and the son of singer Diana Ross.

Now, five years on from Ashlee's return to the spotlight, this is what her life is like.

Ashlee Simpson's career.

If you watched a lot of TV during your teenage years, Jessica and Ashlee Simpson certainly need no introduction.

The pair, who were both born in Waco, Texas, first launched their respective careers in music and television when they were just teenagers.

Jessica, who is the eldest of the two siblings, was the first of the two sisters to pursue a singing career, releasing her debut album 'Sweet Kisses' in 1999.

As her sister began to make waves in the music world, Ashlee pursued a career in acting and in 2002, she joined the cast of 7th Heaven as Cecilia Smith.

The next year, Jessica and her then-husband Nick Lachey launched their very own MTV reality TV show, Newlyweds: Nick and Jessica. 

It was a show ahead of its time. After all, it debuted years before Keeping Up With The Kardashians.

Image: Getty.


While the show chronicled the couple's relationship as a newly married couple, it also provided a platform for Ashlee.

In fact, following the success of the series, Ashlee received her very own spin-off series, The Ashlee Simpson Show, which would focus on the recording of her debut album.

Amid the release of the reality show, Ashlee famously dyed her blonde hair dark in the hopes of distinguishing herself from her sister.

In 2004, Ashlee's debut album, 'Autobiography', was released. Thanks to the success of her reality show, the album became the highest-selling debut album by a female artist that year.


In the years that followed, Ashlee went on to release two more albums – 'I Am Me' in October 2005 and 'Bittersweet World' in April 2008.

Unfortunately, neither album managed to surpass the success of her debut.

In 2009, Ashlee returned to television when she appeared in the revamped series Melrose Place. Although Ashlee played the big role of Violet Foster in the series, she was written out of the show after just 12 episodes.

For almost a decade, Ashlee Simpson stepped away from the public sphere to focus on raising her children. Upon finally stepping back into the spotlight in 2018, the singer looked almost completely unrecognisable from her early days.

In 2018, Ashlee + Evan, the couple's reality series, premiered on E! and the same year they released their debut single together, 'I Do'.

Ashlee Simpson's personal life.

In October 2005, Ashlee began dating her band's drummer, Braxton Olita. The pair's relationship came to an end in July 2006. A few months after her split from Olita, it was confirmed that Ashlee was dating Fall Out Boy bassist Pete Wentz.

In February 2008, Ashlee was spotted wearing a diamond ring on her left hand. Although she initially claimed the ring was a promise ring, the couple confirmed their engagement in April 2008.

On May 17, 2008, Ashlee and Pete were married in California, with Ashlee's father officiating the ceremony.


Following their wedding day, Ashlee changed her last name to Simpson-Wentz and two weeks after the wedding, Ashlee announced her pregnancy. In November 2008, the couple welcomed a son – Bronx Mowgli Wentz.

Ashlee Simpson and Pete Wentz in 2010. Image: Getty.

In February 2011, however, Ashlee filed for divorce, citing irreconcilable differences.


Speaking to Howard Stern following their divorce, Pete admitted that he thought he would be married to Ashlee "forever".

"I thought it was forever," he said. "My parents have been married, I think, 35 years. I don't really know. Forty years, this year, maybe? But at the same time, we were both very young."

He also shared that the couple's place in the public eye also played a role in the divorce.

"I think there's an important thing where you know how to fight, because you can fight with somebody and it's not the end of everything," he told Howard Stern. "But if you don't know how to have those arguments, then they become nuclear. And we were doing this all in the public eye, which doesn't help."

In June 2011, Ashlee began dating Boardwalk Empire actor Vincent Piazza, until they split in November 2012.

She began dating Evan Ross, the son of Diana Ross, in July 2013.

The couple were engaged in January 2014 and got married at Diana's Connecticut estate in August 2014. 


In July 2015, the couple welcomed their first child together – daughter Jagger Snow Ross. In 2018, the couple shared their hopes to have another child.

"I'd love more kids. We're definitely having another one," Evan said.

"I want to finish this album and then definitely, for sure. Definitely one more, and then we'll see what happens after that," Ashlee added.

In April, 2020, Ashlee announced baby number three. A source shared with People, "Ashlee has been wanting another baby for a long time. They always wanted a big family."

In October 2020, they welcomed their son Ziggy Blu Ross. 

And all of Ashlee's kids are adored by Diana Ross, she said recently, adding: "She's such a wonderful mother-in-law."


As for daughter Jagger: "She's become a little superstar; she can perform and everything."

Speaking to the Daily Dish about her marriage to Evan, Ashlee said it's been "amazing" to grow together. 

"I was so thankful I really had found my soul mate. I was a single mum [and] sometimes you're like, 'I don't know where my life is gonna take me.' So the day he walked into my life was a very special one." 


The couple also have a positive co-parenting relationship with Pete Wentz, who now has two more children with his partner Meagan Camper.

"It's great. We have a great family. We're all close friends, thank God," Ross said.

"Seriously, we really lucked out," Ashlee added.

As of recently, Ashlee has been experiencing a public eye resurgence. Late last year she made a rare return to the stage to perform her old song 'La La' with Demi Lovato, as Lovato was regularly covering the song on tour.

Ashlee also announced that she has moved into the interior design space, confirming she is the creative director behind a contemporary interior decor brand, Kempa Home.

Reflecting on her life now, Ashlee said she no longer takes herself "that seriously", adding that age and experience have helped her through the tough times. 

"It is hard. When you're in that moment you're just going and going," she said in an interview with i-D.

"But I look back and listen to those albums and I watch myself and how strong I was when I was younger and how I kept being creative. I'm proud of myself."

This article was originally published on May 1, 2020, and has since been updated with new information.

Feature Image: Getty/Instagram @ashleesimpsonross.

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