When it comes to Mommy and Daddy Joe’s prized golden goose, Jessica Simpson can be a handful at times. If you’ve ever seen her in an interview or followed her career for more than fifteen seconds, you’ve likely encountered something that the singer said or did that made you think, Did that really just happen? It’s not that she’s so scandalous. Jessica is just unique in the sense that she doesn’t care about her image in the conventional sense that many of her fellow celebs do. She keeps it real and will gladly talk about subjects that most people, especially women, would find embarrassing, her personal bodily functions being a favorite topic.
So it should go without saying that Jessica’s actions, captured by eager photographers, may sometimes be in sync with her filter-less mindset. And as you’ll soon see, we had no trouble whatsoever uncovering fifteen of Jessica’s less than ladylike moments. She probably wouldn’t care but her parents might, especially as you’ll see, her mother who is involved in some of these humdingers. When you’re a celebrity and nothing is off-limits when it comes to social media, interviews and the like, it’s a feeding frenzy for tabloids. But when it comes to our dear Jessica, we’re afraid she might have desensitized the tabloids with her carefree ways so we’re happy to present these outrageous images that might have been overlooked. Here are fifteen photos that Jessica Simpson’s parents (hopefully) want to forget.
20. The Infamous Mom Jeans Incident
Poor Jessica. The girl wears one pair of “mom jeans” and no one will ever forget about it. Truthfully, this isn’t the worst photo in the world. It’s just not the most flattering take on high-waisted jeans. Also, that upwards angle never does anyone any favors. Critics and Jessica-haters everywhere have labeled the singer as “fat” in this photo due to the slim fit of the pant legs and the not so slim fit of the rest of the pants which sure have a lot of pockets on them. The gold and leopard print belt is a bit gaudy and doesn’t help to tone down the look. Even though someone could aim a photo on any given street and likely catch a few people dressed worse that Jessica in this photo, this image will forever be linked to a healthy dose of public shaming for her which is why we think her parents would gladly remove it from the face of the earth, if given the chance.
19. Now We See Where She Gets It From
Oh boy, this lovely gem isn’t even a photo of Jessica but we bet that her parents wish this scenario never had a camera pointed its way. What exactly is going on here? Jess’ husband, Eric has got his head resting on his mother-in-law’s well, crotch region while he is giving a big thumbs up. Why? What is the approval in reference to? Was Tina Simpson pretending to give birth to her son-in-law? If so, that opens up a different can of worms. Were they doing some weird lounge chair conga dance? In any case, we sincerely hope there was some alcohol involved to make this frightful situation come to fruition. If this is just an average day at the Simpson household, that’s a little much to bear – even for them. And who was taking the photo? Jessica? Maybe she’s okay with this photo being forever on the Internet but we think her mother may be regretting this doozy while her father likely looked on in horror.
18. When A Beauty Treatment Pic Goes Terribly, Terribly Wrong
There are tons of beauty treatment pics posted on celebs’ social media accounts that are cute and funny. Mud masks, sugar scrubs and facial treatments with pretty floral names all have the potential to be interesting photos to share. But this… well, this is just not in that same category. Jessica has paper mask stuck to her face including her eyebrows while she sits up in bed to take a very awkward selfie. She looks to be in pain and not enjoying herself too much which is pretty much the exact opposite of the concept behind the beauty treatment pic. It’s supposed to show how a girl loves to get pampered, not have paper pasted to their face with a painful attempt at a smile. She gets an A for effort but an F in execution and we think that her parents would agree. This one’s not a keeper. Unfortunately, the Internet keeps everything anyway.
17. Creepy Crawler
There are memes everywhere that call this strange little image “I love carpet” and you can see why. Jessica is staring seductively into the camera while grasping at the carpet on the floor of her bedroom, hotel room or wherever she is. We get the basic idea here. Jessica’s sex appeal is largely a part of what boosted her to fame. But something, actually several things, in this photo just do not add up to a proper smokeshow photo. It might have something to do with the way her body is positioned. Her legs and arms are at an awkward angle that does not look comfortable. It also might have something to do with her environment. Where is she? There’s a chair and a door in the background. It looks like she just fell down and started crawling very strangely. Sorry, Jess, this one’s a no-go and we think her folks would concur.
16. Multiple Nip Slips
Malfunction on me once, wardrobe, shame on you. Malfunction on me twice, shame on me. Malfunction yet a third time – what the heck is going on here? Jessica’s tops and dresses have been caught by paparazzi and red carpet cameras lying down on the job more than just a few times. After the first incident, one might address the issue with the various items available on the market today to prevent situations like this but Jessica is a rare breed of celebrity. She comes as she is and if you don’t like it, well, too bad. Or at least that’s what we think she is saying when she continues to have one wardrobe malfunction after another. Situations like these may not be the boost of confidence her potential shoppers need to try her line of clothing. Pro tip, Jessica… band-aids work great in a pinch!
15. Quality Mother/Daughter Time?
There’s just so much going on here. Where to begin? This obviously isn’t a staged photo. This was a real deal, this is happening, our pants are down and we’re using the restroom moment… oh, a photo opportunity, you say? Why in the world not? Of course, we have so many questions. Did the mother/daughter duo both have to use the restroom so badly that they couldn’t wait for separate turns? Or is this just normal girl talk/quality time for them? What’s with the Popeye-esque arms that Jessica is sporting? Is there a nautical theme to this photo that we’re missing? What is with that tiny child-size toilet Tina is using? More importantly, why is she using it? Did Jessica call dibs on the normal adult-sized toilet? Our final, pressing question is who in the world took this photo? Could it be the same person who took the photo of Tina and Eric on the lounge chair? We are guessing that when you’re in the Simpson circle of trust, you learn to live with these strange little moments and eventually get used to capturing them for all to see.
14. What Happens In The Photo Booth Does Not Stay In The Photo Booth… Unfortunately
We’re not even sure this is a photo booth pic. Maybe they just felt a bizarre photo opportunity coming on and handed someone a camera. But we’re going to make ourselves feel better and blame this one on photo booth fever. When you look at photos of the Johnson-Simpson family, it looks as if Eric is the normal one but based on this photo, you can clearly see that he has a fun side capable of rivalling Jessica’s… or at least, keeping up with hers. Maybe some of her quirky, goofy spunk has rubbed off on him during the course of their marriage? All we can say is that it’s highly probable that Joe and Tina aren’t fond of seeing a man, even if he is their son-in-law, pulling their daughter’s head towards him and licking tongues in a very TMI-way. Call the PDA police!
13. Accidentally Pulling A “Reverse Marilyn”
Sneaky, pesky gusty wind. It’s no friend to women. It messes up our hair and if we’re not careful, gives us a moment like this. In true Jessica fashion, she looks more amused than embarrassed when she finds out that the wind has betrayed her. While it’s definitely true that Jessica is no Queen of England, maybe we can all take a lesson or two from her in how to let embarrassing little slip ups roll off our backs in the carefree manner that she carries with her. Of course, we probably don’t want to go 100% DGAF like Jess but perhaps a little bit of nonchalance isn’t such a bad thing. All the same, this isn’t flattering and does nothing for her image so her parents would probably tame the wind for their little girl and delete this image from history if only they could.
12. “This Stuff Sells But That’s Our Daughter!”
… is hopefully what Joe and Tina said when they saw the result of their little darling’s photo shoot. In 2003, Jessica had a session with Rolling Stone magazine that landed her on the cover as “Housewife Of The Year.” This was a huge time for her. She had successfully emerged onto the pop scene, giving contenders like Britney Spears, Christina Aguilera and Mandy Moore a run for their money. The theme of the shoot played on the fact that she was a newlywed to fellow singer Nick Lachey at the time and the two had a reality show filled to the brim of ditzy as well as gross Jessica moments. The interesting part is that Tommy Mottola who gave Jessica her big break, wanted to promote an “anti-sex appeal” angle with her, going up against her competition without the same tactics they were using. But Hollywood wouldn’t hear of it and the results of this photo shoot speak to that. Her attempt at a sexy eye squint looks awkward and though sex appeal ultimately helped play a role in her fame, her parents probably grimace anytime they see this little number.
11. The Acne Cream Sell Out Days
Adam Levine did it. So did Alicia Keys, Mandy Moore, Jennifer Love Hewitt, Kelly Clarkson, Katy Perry and even Lindsay Lohan back in the day. So why not Jessica Simpson? Because it’s super embarrassing, that’s why. Everyone gets skin blemishes, that’s for sure. But not everyone goes on national TV allowing the intrusive marketing folks at Proactiv to zoom in on your zits in an awkward photo and have you talk about how horrible you used to look. The worst part is that the people at home watching these commercials (which used to be on practically every commercial break) know that you got paid big bucks to shell out some self-humiliation. Money will come and go but images like this will live on forever. Like many pop stars out there, Jessica’s image was everything in her heyday and she may not have fully realized what she was signing up for at the time. We bet Jessica’s parents would pull the plug on Proactiv if they could go back in time.
10. Livin’ Large
We’re not hating on this busy mama of two. Jessica is a beautiful girl who’s worked hard for all of her success. Everyone goes through ups and downs when it comes to our personal health and sometimes we look better than other times but frankly, stages of life like this have got to stick in the craw of her manager-ish parents. Jessica usually looks on point even if she’s experiencing wardrobe malfunctions and wind assaults but photos like this that show her with a little extra to love are in the same category as the mom jeans photo: not wanted, at least in the minds of those who manage her career. For a pretty pop star like Jess, her image is all about not being the girl next door so when her flaws are visible, it takes away from the glitz and glamour her fans has come to expect.
9. Rehab Rumors
Not only is this an unflattering pic thanks to the oh-so unforgiving paparazzi but what it represents is something that surely her parents wish had never existed. There’s a rumor that Eric gave his wife an ultimatum to get sober (allegedly, her use of alcohol mixed with her prescribed Adderall and anti-anxiety medication) or he was taking the kids elsewhere, Eric’s concern for Jessica reportedly bubbled to a boiling point after her strange behavior of HSN. Of course, Joe and Tina shared in that concern for their oldest daughter. These rehab rumors were back in 2015 and things seemed to have calmed down in that area since then but this isn’t a pleasant memory Mom and Dad would be happy to have floating around. Or Eric, for that matter!
8. Jessica, What Did You Do?
For anyone who is young enough to remember watching Jessica’s short lived reality show with former husband Nick Lachey Newlyweds on MTV from 2003 to 2005, you might recall this scene. Most people, man or woman, would be embarrassed or at least not want a moment like this filmed let alone televised and now immortalized on YouTube forevermore. But gold ol’ Jessica “I’m-Keepin’-It-Real” Simpson isn’t most people.
Nick’s brother and former 98 Degrees band member brings a horrific smell to his attention and in search of it, he finds his lovely wife emerging from the facilities.
7. Line, Please
This obviously isn’t a photo but we think you’ll forgive us when you see that Jessica has outdone herself with WTF moments on this live appearance on HSN, pushing items from her Jessica Simpson collection. Mom Tina joins her daughter who appears to be slurring her words and seems a little off-balance. Now, Jessica is known for her ditzy behavior but even Tina seems to be a little concerned about the way her daughter is behaving in this clip. Is it likely that before the live, two-hour shoot was to begin, Jessica had a few too many glasses of champagne while waiting in the green room? Of course it is. Is it just as likely that Jessica acted like a ditz because… well, perhaps she is? This is the girl with the famous “chicken of the sea” question, after all. Then again, soon after this clip was released, rumors surfaced that Eric was threatening Jessica with an ultimatum, pushing for rehab for her alleged Adderall, anti-anxiety medication and alcohol use. We can tell by Tina’s nervous laughter on this clip that she’d prefer if this was erased from television and our minds.
6. The Dumb Question Heard ‘Round The World
“Is this chicken what I have or is this fish?” Ten little words was all it took for the world to confirm that Jessica, who at the time was in her prime as a bubbly pop star in 2005, was not too bright. When she is met by nothing but a blank and dumbfounded stare from her then husband, Nick Lachey, she shamelessly backpedals by saying, “I know it’s tuna but it says chicken… by the sea. Is that stupid?”
Nick then launches into a lesson that one might use to help a child understand the situation and after many more blank stares, she says, “I understand now” but the look on her confused face implies that is the furtherest thing from the truth.
5. Is This From The “Other” Industry?
This racy little number is from a personal (sort of) black and white series that Jessica posted on her Twitter account in honor of Valentine’s Day. It clearly shows that three years of marriage and sharing the responsibilities for two small kids hasn’t taken any of the spice out of their relationship. Jessica is proud of her husband and their fiery romance and happy to show off their chemistry in celebration of the day of love but any normal parent wouldn’t want to see something so intimate, especially to know that it was being posted for the whole world to see! Even though Joe has been known to make inappropriate comments about his daughter’s sexuality and Tina, as you’ve seen, has shared in her daughter’s wackiness, this private moment between husband and wife would make any parent shudder.
4. Drunk As A Skunk
Leaving the Sayers Club one night in 2015 where her brother-in-law, Evan Ross was performing, a very boozy and tipsy Jessica clumsily made her way through the pack of paparazzi to a waiting car, with much needed assistance from her husband, Eric. With the straps of her top falling down and her feet barely able to keep her upright, she made nonsensical requests to the photographers. “Make sure you get a picture of that,” she said, ignoring their other questions and pointing to the ground.
“Of what?” the eager paparazzi asked. “Make sure we get a picture of what?” Someone in the crowd holding a video camera panned down to where she was pointing only to see a puddle in the street.
We can’t blame her too much. She was out having a good time and made sure to have hubby, Eric act as her personal designated Jessica handler. But still, her parents must cringe when they see photos and videos like this of their billion dollar baby.
3. Murky Memories Of A Movie Flop
In 2008, the movie, Private Valentine: Blonde & Dangerous was released onto the world (parts of the world anyway), giving late night show hosts plenty of monologue fuel. A revamp of Goldie Hawn’s classic Private Benjamin, this movie was not. It did so poorly that it was never even released in U.S. theaters. Conan O’Brien said that Jessica’s acting was so bad that the movie couldn’t be released in any English-speaking countries, referring to the fact that the movie was released to Russia and Bulgaria theaters before going straight to DVD in the U.S. one year later. Mom and Dad Simpson like success so this pic is a reminder of bad times and they likely wish this was a “private” disaster that everyone would forget about. Luckily, that wish has been granted for the most part. But in all fairness to Jessica, who can compete with the likes of the great Goldie Hawn?
2. Funny Face
But not ‘haha’ funny. Funny in a strange way. Sure, people make expressions all of the time but Jessica seems intent on pulling strange and rather unattractive faces as much as she possibly can while other celebs try everything they can to make sure the cameras catch only their good angles. This gif was created from a 2006 interview on The Tonight Show and we’re sure that Jessica’s parents wish that she would take her silliness down a couple of notches while on appearing on live television, especially an appearance as important to her career as the famed Tonight Show. Jessica pulled out all of the stops for this interview with her infamous ditzy and wacky behavior even saying at one point, “I don’t know what I’m talking about” to which then host Jay Leno said, “I’m glad you said it, not me.”
1. Can’t Be Bothered To Brush
Jessica’s parents definitely wish their little darling kept her mouth shut when it comes to her well, mouth. In a 2010 Ellen interview, Jessica confirmed a rumor that she herself started when it comes her pearly whites. She said that at best, she brushes her teeth maybe three times per week. The rest of the time, she’ll scrub them with a t-shirt in true raunchy Jessica style. Her explanation as to why she skips out on her personal dental hygiene is still not clear with the series of murky statements that she offered.
“My teeth are so white and I don’t like them to feel too slipperly.” “I need a little coating…” “My lips just slide all over the place.” “I can’t catch up with my mouth.”
She insisted to Ellen that despite this, she has great breath 24/7. Whatever you say, Jess.