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21 Times Jessica And Ashlee Simpson Were Total Messes

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21 Times Jessica And Ashlee Simpson Were Total Messes

Did you know that the term “hot mess” has been officially added to the collection of Merriam-Webster definitions? That’s how much our culture uses the phrase to define “a person or thing that is spectacularly unsuccessful or disordered, especially one that is a source of peculiar fascination.” And spectacularly unsuccessful (as it applies to certain situations), disordered photos of two sisters who are sources of peculiar fascination is exactly what you will find with this list. We all have times in our lives where we might look like a hot mess or feel like a hot mess or maybe sometimes our life is just a hot mess in general, but for celebrities, all bets are off. They get paid obscene amounts of money thanks to their “perfect” appearances. It is certainly within their rights to step out of their homes without a drop of makeup on or without so much as a glance in the mirror. Buttt… cameras will be there waiting. And articles like this will be written. And they know that.

So whether it’s right or wrong, let the judging begin on these 20 pics that captured the hot, messy times of Jessica and Ashlee Simpson. Welcome to this sisterly showdown.

21. Jessica – Messy Momma

Jessica, pictured here around 2013 with baby Maxwell Drew, has definitely seen better days. Maxwell looks like a healthy baby while in contrast, Jessica looks exhausted and totally disorganized. Now being a new mom is no picnic and can certainly take a toll on the sleep schedule, so we’re not trying to pick on Jessica too much here. It’s just that the girl has her own personal glam squad and enough money to employ an army of nannies and au pairs to be with her and the baby round the clock. Maybe she was just trying to spend as much time with her baby as possible instead of pawning her off on a nanny, which is commendable. But people can be harsh when they see this pic of the former Dukes of Hazard remake star. We can’t even repeat the words that were originally tagged to this photo when we found it. Ouch.

20. Ashlee – Booed Out Of The Bowl

The Orange Bowl in 2005 should have been a very exciting time in Ashlee Simpson’s life. She was set to bring down the house and badly needed to do a killer job after her 2004 SNL debacle. Unfortunately, despite an expensive performance complete with pyrotechnics and enough dancers to fill the field, Ashlee’s singing was lackluster at best and it was obvious she didn’t give it her all. While Ashlee’s band played their hearts out and her backup dancers, dressed as cheerleaders in black and white to match Ashlee’s then emo/goth style, literally ran circles around her, Ashlee gave a performance worthy of a high school talent show at best. The crowd at the Orange Bowl was polite enough to wait until Ashlee had finished howling her final note until they collectively mustered up a loud enough boo to be heard from miles away. The sportscasters were obviously shocked and tried to cover up the embarrassment by talking about what was coming up next, but the damage was done. You make me wanna…. BOO!

19. Jessica – Light Surgery Rumors

When you are a household name for more than a handful of years, it’s got to be hard to escape the magnetic pull of beckoning surgeons in Beverly Hills. What famous person hasn’t gotten, or at least been accused of having gotten, a nip and tuck procedure performed? Our darling Jessica is no exception. Clearly, these four photos all show the same girl with differing facial features. Was it the camera angle? Special effects and contouring? The lighting? (They always blame the lighting.) Perhaps the true answer lies in Jessica’s confidential VIP folder at her alleged surgeon’s office. While there are certainly many other celebrities with more damning photographic evidence stacked against them, these photos give us much to think about in the plastic ponder department.

18. Ashlee – Heavy Surgery Facts

We started seeing Ashlee’s face drastically change in the early 2000s during her rise to fame. But it wasn’t until 2006 that the former singer admitted (as if that was necessary for confirmation) that she had her nose done. “If people want to get surgery, it’s a personal thing. But it’s not something anyone should rush into,” she said. “Once it’s done, it’s done.” Indeed. But her confession doesn’t seem to have helped. Her continued facial changes in the following years landed her on the cover of gossip magazines, but Ashlee said that she remained unfazed by the rush of attention.“I don’t get bothered by people saying what they say,” she said. “I’m a happy person, and I’m happy with my looks. Everybody always has an opinion. One minute they’ll love you; one minute they’ll hate you. When you go home to sleep at night, [the important thing] is to feel good about yourself. And I do.”

17. Jessica – The One-Eyed Wonder

It’s a wonder how Jess’ people allowed this photo to get taken of her looking like a sloppy, stumbling wreck. But then again, if it was your job to keep a watchful eye on this woman while she was out enjoying a wild night of fun, and make certain that no embarrassing photos of her were leaked, you would either quit or be fired the very next day. Jessica Simpson has proven time and time again that she can’t be trusted when fun times and booze are mixed. Or maybe just booze. There are plenty of photos out there (fairly recent ones, too) of Jessica practically tripping as she exits a club, looking bleary and half-asleep when she exits a club, having some sort of wardrobe issue while she exits a club… you get the idea. When Jessica is exiting an establishment that serves alcohol, the paparazzi are aimed and ready for a payday gold mine with their cameras.

16. Ashlee – The Lip Sync Scandal That The World Isn’t Ready To Let Go Of Yet

This particular hot mess is an especially painful one. That’s because, as many speculate, it led to the end of a career for young Ashlee. If you’re somehow unfamiliar with this incident, it happened way back in 2004, when Ashlee was at the peak of her success. Sure, now you only hear about her when the paparazzi manages to snag a photo of her with her second husband and son. Back in the day, Ashlee was doing pretty well for herself. She made a ton of album sales for Autobiography and her songs were constantly being played on the radio, which is why Saturday Night Live asked her to come on as their musical guest. By the second performance on SNL, things took a rocky turn. Ashlee’s voice started singing but her lips weren’t moving. Shocked, Ashlee turned to her band as if it were their fault. Then she started to do a weird dance before walking offstage. Sadly, Ashlee’s career never fully recovered from this blunder.

15. Jessica – No Makeup Girl Next Door

While some say that Jessica’s no makeup pic looks pretty tragic, she actually doesn’t look that bad. Maybe she looks awful for a pop star/clothing line mogul but for the average Jane Doe walking around in your neighborhood? Eh, she could be anybody. Even the girl next door. If you saw Jessica’s makeup-free photo in the grocery store, you wouldn’t secretly snap a photo to show your friends later and say, “Look at this horrible-looking human being that I saw earlier”? Of course not. But back to the earlier point, seeing as how Jessica is one to pride herself on her appearance, it is kind of strange to think that she would walk out in public looking like she just woke up. For normal people, this look is just an everyday I-don’t-care look, but for someone with an estimated net worth of 150 million dollars, this is an official hot mess look.

14. Ashlee – No Makeup Nightmare

While Jessica doesn’t look amazing without makeup, at least she is recognizable. Not so with Ashlee, who in this makeup-less photo looks like a mere shell of her dolled-up self. Poor Ashlee. She has always been in the shadow of her overachieving sister, who seems to have such an easier walk through life. Sure, Jessica has had her fair share of controversies, but nothing that has come close to ending her career or even diminishing it. Heck, the girl is not even known for singing anymore, and she’s still super famous. Sadly, poor Ash is known only as the girl who was caught lip-syncing on SNL, and she’s back to being just Jessica’s little sister. Even her makeup-free photo can’t hold a candle to her sister’s photo.
#littlesisterissues

13. Jessica – Caught With Her Hand In The Cookie Jar

What a shocked look she has on her face! But maybe her hand was in her own cookie jar for a good reason like needing to make a necessary wardrobe adjustment. As seen in the other photo, Jess has had plenty of low-rise disasters that have us reaching for emoji stickers to cover them up. With all of the outfit trouble that Jessica has, judging by the sheer volume of photos we have gone through of her over the years with something exposed, we have to call her out for being a total mess in this regard. Yes, the girl has to do more outfit changes in a year than a normal person has to do in say, ten years, but really… how hard can it be to keep your top up?

12. Ashlee – Year Of The Hot Mess

Poor kid. That’s all we can think of when we see this pic of Ashlee, in the mid 00’s looking confused and miserable or making a funny face on purpose. In either case, the girl looks like a complete mess and in need of some life coaching, perhaps. Ashlee has always seemed a bit lost to us. But it couldn’t have been easy for her. To say that the Simpson girls had an equal shot at success would not be a fair statement. Ashlee has forever lived in her big sister’s shadow and had to fight to prove that she deserved her place in pop stardom on her own, because she was constantly being judged on “only being where she is due to her sister’s fame.” We’re definitely not saying that last part isn’t true, only that it couldn’t have been smooth sailing for her. 2005 was the year Ashlee realized her career was heading for a nosedive.

11. Jessica – Poolside View

You’ve got to hand it to this girl. She is nothing if not a true performer at heart. Though a good question is who is she performing for, and a better question is, why exactly is she putting on a show via her chaise lounge pool chair? That looks like her husband, Eric Johnson is in the pool with sunglasses on, but it’s not quite clear. We’ll just say that what this teary-eyed emoji is covering up is not safe for the eyes of children, and definitely not safe for work. Seeing as how there’s another person (at least one) in the pool as well as her husband — if that is indeed her husband — this leg lift was very inappropriate, very much a mess and very much the Jessica that we have come to know and love.

10. Ashlee – Not All That She’s Cracked Up To Be

This very weird photo is of Braxton Olita holding what appears to be a saltine cracker to Ashlee’s forehead. Olita joined Ashlee’s band in 2004 as a guitarist. He can be seen in several of her music videos including “La La”, “Shadow”, “Pieces Of Me”, “I Am Me” and “Boyfriend”. He was also featured in at least two episodes of The Ashlee Simpson Show on MTV which came after Jessica’s Newlyweds show. He and Ashlee were romantically linked for a short while in the pre-Pete Wentz days. Following Ashlee’s crash and burning singing career, Olita went on to be involved with Thirty Seconds to Mars from 2009 to 2011. The following year, his band U.G.L.Y. was signed to CBE, Chris Brown‘s record label and in 2015, he played keyboards and guitar for Ceelo Green, Kiiara and Kid Cudi. So though his romance with Ashlee soon burned out, his music career has lasted longer than hers and that definitely counts as a notch towards Ashlee’s mess total.

9. Jessica – Foot Malfunction

We are not sure how this Fred Flintstone fiasco could have happened to this fabulous fashionista as she and her hubby, Eric Johnson, attended a Tom Everhart gallery event and a dinner at Vic’s restaurant in New York City. Maybe Jess thought that her toenails needed to be filed down a bit and she assumed that the streets of SoHo were as good as any emery board on the market. Or maybe her shoes were just too short to accommodate her lengthy toes. Perhaps she thought her fancy foot bling might distract attention from her red painted toenails that were left out in the cold? Not so. No gold ankle bracelet could distract anyone from seeing those digits dangle on the pavement. Tuck in those toes, Jess! Or just get fitted for properly sized shoes.

8. Ashlee – Still Invisible

Ashlee’s 2007 single “Invisible” showed us a very different side to the singer. Gone was the dyed black hair with the sharp fringed face-framing cut, gone were the skater boy shoes and the baggy pants. Enter Ashlee’s new, softer look. Though she plays the part of a boxer in the music video for her song, it’s easy to see that her style is much more feminine. Everything is different about Ashlee including her singing voice. Her punk voice is replaced with a country-like twang. The lyrics are telling of what we can only assume is bottled up emotions from her life as Jessica’s little and less famous sister. “You’re the one who looked right through me; Now you’re saying that you knew me; When I was invisible.” Sadly, Ashlee’s reinvention failed to take off and she remains lost in Jessica’s shadow… still very much invisible.

7. Jessica – Going Public With Her Personal Hygiene Routine

Even if you’re the biggest Jessica Simpson fan known to mankind, chances are you probably don’t care to see her demonstrating how to use a Neti pot on herself or using an ear candle with a Papa John’s pizza box as an ear wax catcher, right? And if you do care to see these things, you might want to keep that info to yourself. But you would enjoy watching Jess stick the spout of a Neti pot, which looks like a small teapot, up her nostril and watching the disgusting mucousy mess that comes out the other side. A Neti pot is a nasal irrigation method that helps to clear away crusting in the nasal passages. In the other photo, Jess is seen holding a lit candle sideways in her ear. Ear candles are a homeopathic approach to pulling out yeast and wax buildup from the ear canals. While we applaud this girl for taking her hygiene seriously, there are some things that just don’t need or deserve to be documented. Posting a photo of yourself with a teapot up your nose most definitely makes you a total mess.

6. Jessica & Ashlee – Pulling A Miley

Pop stars and celebrities of any kind are like open targets for personal criticism of just about any kind. Jessica and Ashlee know this well as they have both received negative comments about their tongues. Internet critics have called both of the sisters’ tongues “ugly” and “gross”. We would just assume that Jessica and Ashlee were copying Miley’s famous tongue pose, but knowing how Jessica doesn’t mind being seen unfiltered, to put it nicely, we would have to say that is all Jessica. But since little sis Ashlee has been known to, or at least accused of, copying others in the past (ahem, Avril Lavigne) we can’t put it past her to copy Miley. Do you agree with others that Jessica and Ashlee’s long, serpent-like tongues are ugly and gross?

5. Jessica – Not Acting Like A Classy Lady

There have been plenty of “sightings” in recent years and continuing today of Jessica caught stumbling out of nightclubs, usually flanked by her husband, Eric, and one of “her people” just to make sure there are no photos of Jessica face down on the pavement pasted on every magazine cover the next morning. While exiting the clubs, Jessica always looks really out of it, as evident by her glazed over expression, clothing that is falling off of her and her hair and makeup are usually a mess. In these photos, Jessica is seen with a hand trying to cover up her top which appears to be torn leaving her bra exposed, as Eric protectively tries to hurry her into a waiting vehicle. We hope nothing really terrible happened!

4. Ashlee – Grungy Girl

Ashlee’s grunge-tastic days didn’t last too long after her string of singing snafus. But during the time of her skater/grunge look, Ashlee received some criticism stating that she was copying the look of another young, female singer with a skate punk persona. Avril Lavigne had been on the music scene since she was 15 and performed live with Shania Twain. Known as the “Pop Punk Queen”, thanks to her success and the impact she had on the industry, Lavigne is thought to be a major development of pop punk music, and she paved the way for female-driven, punk-influenced pop music. But we’re not sure Ashlee said thanks, because Avril dated Ashlee’s ex, Ryan Cabrera, soon after he and Ashlee broke up. Battle of the grunge girls!

3. Jessica – The Movie Roles That Weren’t Meant To Be (Hers)

Maybe you already knew that Piper Perabo won her Coyote Ugly role over Jessica, but you’re probably thinking to yourself, Pretty Woman? Wasn’t Jessica around nine when that movie came out? And you would be correct. But Jessica’s dad, known as “Papa Joe” for his helicopter dad status when it comes to Jessica’s career, pushed for a remake of the classic movie to be shot with — you guessed it — none other than his precious daughter, Jessica, starring in the lead role. “She thinks this one’s got ‘hit’ written all over it,” someone close to the family said. “Her father has been telling anyone who will listen that she’s the next Julia.” The next Julia? Seriously? Straight to DVD Private Valentine: Blonde And Dangerous and even the Dukes of Hazard remake with a 14% Tomatometer rating on Rotten Tomatoes is all well and good for Jessica to try out her acting chops, but we feel confident that if someone had given the singer a green light to reprise the role that made Julia Roberts a star, Hollywood would be smacked with petitions and protests so fast it would knock the tinsel right out of town.

2. Jessica & Ashlee – Painfully Pregnant Twins

We’re not trying to pick on pregnant ladies here but we just had to comment on the fact that both sisters chose to wear nearly identical outfits of black, sheer material that is pulled so tightly, almost painfully stretched over their swollen bellies that it looks like it’s starting to rip. Given Ashlee’s copycat track record, we wonder if she took notes on her big sister’s pregnancy style. Was Jessica the inspiration for Ashlee’s choice of a tight-fitting sheer black dress, tight black jacket, and oversized sunglasses? Ashlee’s long blonde hair is also the same length as Jessica’s and worn loose, too. Maybe it was just a coincidence, maybe they dressed the same because of their similar genetic makeup, or just maybe, Ashlee copied her more famous sister for this painful look.

1. Jessica – The World’s Messiest Music Video

Jessica’s 2003 hit “With You” gave us an up-close and personal look into Jessica’s life. For those who had a squeaky clean image of the singer and had never watched an episode of MTV’s Newlyweds, they had a big surprise in store for them. Jessica sings, “The real me is a southern girl with her Levis on and an open heart; Wish I could sing to save the world; like I was super girl; The real me is to laugh all night lying in the grass just talking about love; But lately; I’ve been jaded life got so complicated”. Life certainly seemed complicated for Jessica, who lays in a pile of her clothes on her bedroom floor. At one point, she takes a pair underwear and puts them on her face before flinging them at the camera. Then there’s the golfing scene with her “adorable” nickname emblazoned on the back of her top. Um, real cute, Jess!

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