Why did Jessica Simpson’s entertainment career go down the shitter?

I date it back to this moment. It was all downhill from here.

She's got a zillion dollars from slapping her name on crap. I see her stuff everywhere and I am ashamed to admit I've bought her stuff before-- it's cute and affordable. Why would she want to deal with the music industry?

We really went after her father and manager, Joe, here back in the day. Deservedly, mind you.

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Lest we forget this absolute abomination. I have mixed feelings about Jewel as a person, but she is a true talent and is too much of a good sport to ever give an honest recollection of this horrifying spectacle.

Because her uber quren father/manager was an idiot.

R5, ha... Jessica couldn't stop being all "at heart really I'm a black chick in a white blonde's body!" .... or, trying to. Those side to side neck weaves and frightening grimaces, oy.

OP, did you hear her singing and her songs? That answers your question.

Ultimately, she had so little to offer. She was a flash in the pan

Can I get 🎶 my money backkkkk ♬

Annoying, untalented, unintelligent, and ugly. Same goes for her bird-beaked sister. They are both dumb, tasteless Texan Wal-Mart whores with electra complexes.

Those Mom jeans killed her career

LOL R10

Fuck the original is horrible

That is not the original! This is the original and it's awesome

R14, agreed, it's a classic.

Nancy's original is 60 years old in 2025.

Jessica and Beyonce had almost identical career beginnings and they both made a killing. Country Texas girls whose dads were hell bent on making them successful. They really just had to maintain what their parents established and not do anything really crazy.

Jessica's music career was not noteworthy, but she somehow used her popularity from the reality show with Nick Lachey to do other things.

Shoot me, but I actually liked that performance with Jewel. Jessica was totally into it and giving it her all, not trying to be cool.

IMO, Jessica has got some problems: alcoholism, maybe an eating disorder (goes from fat to skinny, yoyo).

She had a cute line of shoes for a while.

But I'm amazed at how much mileage she's gotten, able to sell all of her merchandise.

Joe Simpson: first he's commenting on her "double-Ds" (big tits), then he's seen on the beach with a twink. What gives?

She came after Britney and Christina, and there wasn’t room in pop for three dumb blonde girls at the same time.

R18, that's why the performance is bad. Jessica oversings every word and looks completely out of her element.

She blimped out…

[quote]Those Mom jeans killed her career

She gained a lot of weight and has a drug addiction-- pills, alcohol and probably other things too. She is better off slapping her name on retail items. Her dad steered her in the right way.

She and Britney looked really similar when they started out.

She had all those kids which resulted in the major weight fluctuations.

r17 Beyonce is from Houston suburbs-- not really country as Houston is the 4th largest city. I mean guess all of Texas feels country I guess.

[quote] She had all those kids which resulted in the major weight fluctuations.

She also ate all that food and that resulted in more weight fluctuations.

A lot of black people in Houston are "country" and some even keep horses in the city limits. I have no idea about Beyonce though. She's never been interesting to me. I don't think she's from a 'black people owning horses' part of the city (Sunnyside or Acres Homes).

R23 And then she LOST a ton of weight and looks like Skeletor now. Weight loss - another addiction.

Kennedy Center.

There is something very wrong with her. I think she's crazy.

She was mildly talented and her affected singing was....different? Her biggest claim to fame was marrying Nick Lachey and the reality show. She was smart and has since made a killing in kmart level fashion with her shoe line and other products. She made more money in that than she ever made being a pop star

[quote] Kennedy Center.

Betty Ford Center.

Because when you look up mediocre in the dictionary, her picture is there.

Very simple. Because she had no marketable talent. Looks will only take you so far when you're dumb as a bag of dirt and can't do anything to entertain people other than stand there and look pretty.

And then she became a big fat woman.

Her figure was actually fine during the “mom jeans” era. That outfit was just spectacularly unflattering.

Much prefer her look then ti the current skeleton look. She looks very sick right now.

She had a period in between when she gained 100 pounds or so and was unwell then, too.

Even in that Dukes of Hazard video, she looks sickly. She was being sold as thin and sexy, but she had no curves (they had to pad her costume.)

She supposedly had a big drinking problem, which contributed to some of the massive weight gain.

[quote]She was smart

Said no one ever...

If I recall correctly, back in her singing days, Miss Simpson singing repertoire included "God Bless America" sung as a torch song.

Very bad taste and poor judgment.

I see nothing wrong with torching up patriotic songs.

Is her dad still stealing her dresses to wear to gay parties?

r33 snaps in z formation.

r35 She has/had a better voice than many white pop singes like Britney Spears. She had talent.

She had some basic vocal talent and power, but she didn't have the training she needed to learn how to control it. She sounded like she was wailing most of the time. Not quite as bad as Christina's screaming.

Xtina is 100x the singer Simpson is. Simpon was D U M B. I remember MTV did a tribute to Janet Jackson and on comes Jessica talking about how much she loves Janet, so much she does escapage in her show. Yeah not escapade. ESCA PAGE....The whole family is not that bright. Look what her sister Ashley did to her career in one minute on SNL.

She made weird faces when she sang.

She also has very strong facial features, and so when she's skinny she looks a little scary and mannish.... and then with the crazy eyes wack faces when she sang.. yeah not good.

She looked better in the face when she was a chunked out Texan heffa.

She married a jobless ex jock and her sister married a gay man.

Her sisters leprechaun dance is a moment for the ages.

The constant screaming she called singing.

She's better than her sister, Asslee.

Thank God that one gave up on a singing career.

OMG @R49! Good news that was hysterical. LOL

That Ashlee Simpson SNL moment was awesome. I think my jaw was actually hanging open. Almost nobody liked her in the first place, and to get to see her attempted pop star career just implode itself on national TV in an instant.

I think Jessica and her husband are unofficially separated.

Jessica is very likable like Britney, Asslee is very Jamielyn spears

She was too busy getting fucked by that hottie from 98 Degrees.

Who’d want to do anything else?

I think the breakup with Nick and the killing of the newlywed fun narrative is what killed it for her. People got that there wasn't much to her after that.

She sings through her throat and you can see her straining. It’s not pretty.

I think she traded in the drinking for medication. Remember the Pottery Barn commercial? She looks insane. And that's not the only televised appearance where she looked and acted very strangely. (intoxicated on something)

This TikToker had a little fun with the Jessica/Jewel footage

"Same goes for her bird-beaked sister."

Ease up on Ashlee. She has a cunt for a mother-in-law.

Off topic but DL fab Teri Garr is dancing behind Nancy in the video at R14.

She's back in the studio after 14 years and got a face transplant, amidst speculation that she and her husband have called it quits.

Looks like she's been rebuilt from the standardized sex doll pattern.

She looked better heavier. Her face is horrifying without some fat padding it.

She’s definitely someone who looked better with some curves.

She’s got those giant turd lips now. 👄

You’ve got it all wrong. At the height of the TRL pop era with Britney and Christina, her debut album sold 2 million and her next album in 2001 went Gold. She was a C-list answer to Britney and Christina along with Mandy Moore.

She didn’t start selling records until her reality TV show and that album was not a crazy seller either. It was flopping until the TV show became a hit.

And then her next album after that was a flop so she decided to go country and that was a massive bomb.

Jessica can sing but I don’t think she had any vocal training and doesn’t know how to control her voice.

Christina Aguilera has the same issue.

Just because you can hit a note doesn’t mean you know how to control it enough to make it sound good.

That’s why when Jessica and Christina are belting high notes, they look like they’re in pain and a lot of the times, the lose control and their vocal cords tighten up on them and they sound like a kicked chihuahua.

So Jessica has a voice she just never learned how to actually sing with it.

At least she’ll never be as awful as her sister.

R63 She's a glutton for punishment. NO ONE wanted it then, and they damn sure don't want it now. You cannot sing. Accept it already.

R70 She deserves every bit of what she got for that.

I thought this was fake when I first watched it. My mind is blown

She has no talent and she rarely brushes her teeth.

God, that was horrible, r73. Especially the way she was trying to make it all sexy, and then Sharon Osbourne shows up in the middle of it.

R75, I cannot believe Ozzy agreed to this. You know Sharon wanted to kill Jessica deep down lol.

Why did she HAVE a career in the first place? That’s the question.

r77, teenage tits.

R78, those were double Ds!

JS=white trash

Although definitely a step or two up from Britney (y'all!), r80.

At least she seems to have a good relationship (and custody) of her kids. And she has made a career (with her clothing line) past her initial teeny bopper pop singing career.

She looks like Barbra Streisand

[quote]She's back in the studio after 14 years

Yeah, ain’t nobody checking for new Jessica Simpson music today.

Is she extremely fat right now?

No, she's extremely thin and unrecognizable.

[quote]Why did Jessica Simpson’s entertainment career go down the shitter?

Think of it as something like the salmon returning to their source to spawn.

r56 Nick Lacehy is rumored to have been hung like a peanut, so Jessica was probably not getting a good bang out of anything.

Nick and Vanessa Lachey have been together for 18 years now (married for 12 years), and she even gave him an ultimatum to marry her or move the fuck on (the basis for one of their reality shows).

He can't be all THAT teeny or bad.

R82 Barbra would never allow the press to get a pic of the right side of her face like that.

Also, it seems Jessica wasn't the impetus for (or in the very least, hurt by) the divorce:

[quote] “So, Nick, you’re with another already? Seems that you forgot the love you spoke to me,” the fashion designer wrote in diary entries included in the paperback edition of the book, released in March 2021. “I’m saddened beyond belief. Alone in the dark, with no one to call my own.”

[quot]Nick and Vanessa Lachey have been together for 18 years now (married for 12 years), and she even gave him an ultimatum to marry her or move the fuck on (the basis for one of their reality shows).

Nick had another reality show with the second wife? Is he really that interesting?

She was pretty and had a hot body, but that was it. Also, she suffers from mental illness like so many young sex symbols.

I'm not the biggest Jessica fan, but Nick definitely married up and marrying Vanessa was definitely a downgrade.

He has a few reality shows, actually, two of them with his wife. The Ultimatum, Perfect Match, Love is Blind. All about finding love.

He's made his living off reality shows since his music career fizzled.

R93, they go well together, though.

I think he and Vanessa are good together.

Jessica is still cray-cray after all these years.

Caterwauling

R92, who else suffered/suffers from mental illness?

R94 He never really had a music career. 98 Degrees were a third rate boy band just like Jessica was a third rate Britney / Christina.

98 Degrees were like the Magic Mike of boy bands. Just eye candy, their music didn’t matter. It was awful too.

r99 who cares? He was famous for it, for probably a half of a decade. He's parlayed that into a continuing career, 20+ years later.

Splitting hairs is kind of silly.

R100 My point is he’s been more famous for his reality shows. Guarantee he’d made more money off his reality shows than he ever has his music career.

As a solo artist, he only had one album that was certified Gold. That was it lol.

True, r101.

This bitch is BACK. With new music. And she looks crazy!

She is super-wealthy.

Breadcrumbs? More like FAT ROLLS!

I honestly don’t remember her ever being a singer. I can’t name one song. She had a reality show then a makeup brand, a shoe line…then she disappeared.

Being related to Ashley Simpson probably didn’t help either.

Being related to Ashlee Simpson? The only reason Ashlee got put on in the first place was because she was Jessica Simpson’s sister. Granted, Jessica wasn’t the hit machine that her contemporaries were, but she did have a couple of moderately well-known tunes. Her debut single, the saccharine “I Wanna Love You Forever,” was a top 5 Hot 100 hit (that I hated, btw).

🎵 I know I meant to say no! 🎵

I can't believe this is even a question.

she never had any career to begin with

She never seemed to have a brain in her head.

🎵 His ways are powerful, I can hardly breathe 🎵

Chicken of the Sea.

Allegedly she’s so stupid that when she was dating Tony Romo, he always had to take the elevator down to the ground floor to let her in in person when she would come to see him, because her pea brain couldn’t remember the four digit code he gave her to access the building herself. Apparently this happened over and over and over again, lol.

She looks exactly like a person I used to work with, and she was a total and complete beyotch. Now I know who she looks like

I saw her in 1999 when she was the opening act for Ricky Martin's "LLVL" Tour. All I can remember is that she sounded screechy to me.

Her career went nowhere because I was the more talented and prettier one

She doesn’t have to.

What career?

Even by 00s bubblegum pop standards, her music was quite bland and forgettable. Her squeaky voice didn't help. I will admit that "With You" was a guilty pleasure of mine, though.

I didn’t think people ever liked her music. I know that reality show of hers was popular and her fashion line has done well.

Sweetest Sin was her best single despite her annoyingly breathy vocals.

R120, her debut single, I Wanna Love You Forever, actually went platinum. But she was horrible.

Such a wannabe Britney in the 00s.

Thing is, these popstars didn't have to get all sexual. In fact, in the next decades Taylor Swift proved that. Girls wanted more lyric depth.

R123, they were pressured to by the record companies. When Britney came, she made it so all these record labels wanted their own Britney. Which is just one of the reasons why I hate her. Before Britney, teen pop was strictly directed toward teens and those who were younger. But with Britney, it was taken seriously. Fuck her!