Jessica Simpson, 44, reveals surprising heartbreak from her twenties
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Jessica Simpson has revealed a heartbreak from her twenties when she was dropped by her record label in 2008.
She didn't understand why she was dropped after her hit country album Do You Know came out and it led her to take a break from music, she revealed during an interview with Fancy Hagood for an upcoming episode of Trailblazers Radio.
'I took a long break,' Simpson, 44, told Hargood via People. 'I was mad at music a bit. After being dropped with a number one country album, I was dropped and I just never understood it.
'They just said I would never recoup if I didn't give them part of the brand, but my brand was already successful.'
Do You Know debuted at No. 1 on Billboard's Top Country Albums and hit No. 4 Total Album Sales, but her record label decided to drop her anyway.
Simpson's first album, 1999's Sweet Kisses was the first of seven albums she recorded by 2010 and then she stopped making music for 15 years.
Jessica Simpson has revealed a heartbreak from her twenties when she was dropped by her record label in 2008; seen in 2005
She didn't understand why she was dropped after her hit country album Do You Know came out and it led her to take a break from music, she revealed during an interview with Fancy Hagood for an upcoming episode of Trailblazers Radio
Jessica also said that she was warned not to pursue a career in music.
'They told me not to do it. They thought it would ruin my career just like they thought reality TV would ruin my career, and it didn't.'
But Simpson just wanted to be relatable to her fans.
'That's so important I believe as a musician, I'm not going to be the one up there that [is] like, "Oh my God, I want to be just like Jessica."
'I want people to say, "Oh my God. I'm just like Jessica." That just works for me. That thought process,' she said.
The I Belong To Me singer also told Hagood that she had to get her mindset in the right place to return to the music industry.
'I feel like there's so many façades that we put up, so many different things,' she explained.
'This time, I know I have three kids and I want to be a good role model to them, but they know me just the way this music is, which is so nice.
'I took a long break,' Simpson, 44, told Hargood via People. 'I was mad at music a bit. After being dropped with a number one country album, I was dropped and I just never understood it'
'They just said I would never recoup if I didn't give them part of the brand, but my brand was already successful.' Seen here in 2009
Do You Know debuted at No. 1 on Billboard's Top Country Albums and hit No. 4 Total Album Sales, but her record label decided to drop her anyway. Seen here in 2025
'Because my kids have thought that I've been putting out music this whole time because I've had writing sessions at my house and I wanted to put music out a long time ago,' Jessica explained.
'I've always wanted to put music out. It just never felt like the right time. And I'm an intuition gut follower.'
Jessica made her long awaited return to music in March with her EP Nashville Canyon, Pt. 1.
'This is where I discover myself,' Simpson said about Nashville. 'This is where I'm born free… I did a gospel record at 14 here.'
She continued: 'I got to write my first songs here. I wrote my whole country record here, and I was always so safe.'
She chose to record in Nashville after her eldest daughter, Maxwell, 13, wanted to celebrate her birthday in the city.
'Instead of singing Happy Birthday, she wanted us to sing I Saw the Light and play Hank Williams that morning we were in Nashville because that's where she wanted to go… And she'd never been.
'And I woke her up with that song and it just hit me. The light. It was like the light's here,' she said.
Simpson's first album, 1999's Sweet Kisses was the first of seven albums she recorded by 2010 and then she stopped making music for 15 years
Last month, Simpson reflected on the earlier days of her music career, during which she was pitted against other up-and-coming artists.
In her latest interview with Rolling Stone, the Texas native — whose fans think she's plotting a revenge TV show — named the two other blonde music artists she struggled to catch up with.
Looking back on her rise to stardom, she told the magazine, 'I was never gonna win because I had someone like Britney [Spears] and Christina [Aguilera] ahead of me, who were selling so many more records.'
Describing her relationship with her record label at the time, she noted, 'I didn’t want to dance, I didn’t want to wear a head mic.
'But I agreed to do it, because I worked for Sony, and I didn’t want to let them down, and I felt like I was constantly letting people down. Even myself probably, because I wasn’t singing words I wrote.'
It wasn't until she began writing her own music that she was finally able to achieve her first chart-topping single.
