The entertainment industry seems like a literal magnet for a whole variety of creeps, so it’s not a big surprise that sometimes two creepy people will find each other and fall in love. Lots of celebrity couples consist of two highly messed up individuals who choose to reveal their weirdness to the world. Or in many circumstances, one seriously creepy person with no sense of boundaries will find someone young or naive enough to manipulate into whatever they want. But some stars just have that certain je ne sais quoi that makes them too narcissistic, out of touch, or uncaring enough to display their creepy behavior to the world without shame. And creepers are kind of like snowflakes, they all have the same basic makeup but when you look closer every one of them has their own specific brand of gross that no one else could, or would ever want to, replicate. These celebrity couples definitely make us feel weird, and it is usually caused by a variety of creepy factors.
When it comes to vomit-worthy behavior, no one can deliver the goods like a scummy weirdo with a whole lot of money and no one to refuse them, so these famous relationships really do have every horrifying Maury episode twist that you could think of. These creepy couples either cross several lines or veer very close to the point of making us uncomfortable. So which Hollywood couples shamelessly take the ick factor to levels that most people couldn’t even imagine?
15. Woody Allen Married Soon-Yi Previn, His Girlfriend’s Adopted Daughter
Well, we might as well get this infamous pairing out of the way right off the bat, because quite frankly, it’s pretty much impossible to write a list of creepy as hell celebrity couples without including Woody Allen and Soon-Yi. They’re one of the original gross Hollywood couples, and for very good reason. Woody met Soon-Yi as a child, and he met her because he was in a long term relationship with Soon-Yi’s mother, Mia Farrow. After being in a relationship with Farrow for years their relationship came to an end, because Farrow discovered that Woody was sleeping with her teenage daughter. Woody and Soon-Yi wound up getting married and having a few children together, despite the fact that Woody already had children with Soon-Yi’s mom. Oh, and of course Soon-Yi cut off contact with her mother and the rest of her family because of the relationship. And if that’s not bizarre enough, the couple actually acts as if people are overreacting to the grossness of their relationship.
14. Jay-Z And Beyonce Aired Their Dirty Laundry To Get More Money From Their Fans
Jay Z and Beyonce are one of the most successful, famous, and wealthy couples in Hollywood, so it might be a bit of a surprise to see the pair on a list of the creepiest celeb couples. However, they really have earned that title lately. Even individually they have more money than most people on the planet, so it’s a little strange that they suddenly decided to blow up their own cheating scandal spot on both of their albums years after this family drama apparently began. Being that loaded and then airing all of your grimiest dirty laundry in the hopes of making more money seems a bit shady, but even that would be something that could be overlooked if it hadn’t been for Solange pummelling Jay in an elevator years ago with Beyonce just chilling in the background. It was a shocking sight to see at the time and a massive news story that fuelled massive speculation and made Beyonce’s sister look horrible without the context, and the couple just pretended like it wasn’t happening. If there was a time to come clean to the world, that was it, so leaving Solange flailing in the wind just so they could capitalize on their relationship problems seemed a little gross.
13. Scott Disick Is Dating 19-Year-Old Sofia Richie
Sofia Richie doesn’t have much of a public profile yet, which makes sense because she’s a young and a model with middling success and her real only claim to fame before her new relationship was the fact that she’s Lionel Richie‘s daughter. However, Scott Disick certainly has a pretty big public profile, and almost all of it is bad. He actually has his moments where he seems nice and funny, but his longterm substance abuse problems as well as his problems in his relationship with Kourtney Kardashian have been a really long, horrible downward spiral that has been going on for years. I certainly understand why Scott and Kourt wanted to finally call it quits, but Scott moving on to a teenage girlfriend who appears to be nothing more than a party buddy is really not a good look for either of them. A teenage girl and a thirty-something addict is a train wreck waiting to happen, and the fact that neither of them seem to realize it is unsettling.
12. Courtney Stodden And Doug Hutchison Have Decades Between Them
Not only is this coupling creepy as hell, this is a couple that built all of the fame they have on the fact that they’re a creepy as hell couple. Character actor Doug Hutchison married Courtney Stodden when she was just 16 years old and he was in his mid-50s, which isn’t just gross, it’s actually illegal in some states. In fact, Stodden’s mother had to sign off on the marriage in order for Courtney to be able to go through with it, and apparently Courtney’s mom had no problem with the arrangement, even praising Hutchison for how well he treated her daughter. Considering that Courtney’s mom was willing to marry Courtney off to a man she barely knew and who was older than she was, Courtney’s life with Doug actually may have been an improvement from her childhood home life, but that doesn’t make it any less cringe-inducing. Honestly, it makes it even grosser.
11. Hugh Hefner Married Crystal Harris, Who Was Several Decades His Junior
Hugh Hefner built his business and career around creeping on young, attractive women, so it’s no shock that he wound up on this list either. And when Hefner married Playboy playmate Crystal Harris at least she was in her mid-20s, so she actually isn’t even close to the youngest woman on this list (ew), but a twenty-something woman marrying an octogenarian is undeniably icky. And Harris may have come to that realization at some point during their relationship, because she broke off their first engagement only days before they were set to marry, and reconciled with Hefner later and married him after their second engagement period. And there is nothing inherently gross about elderly men, but there is definitely something inherently gross about elderly men who feel like they’re entitled to stunningly beautiful young women. I guess the money may have been worth it to Crystal, but ugh, damn.
10. Hulk Hogan Married Jennifer McDaniel, Who Looks Just Like His Daughter
Yeah, so this isn’t some random picture of Hulk Hogan with a pair of twins. This is a picture of Hulk Hogan with his daughter Brooke on the right, and his new wife Jennifer McDaniel on the left. McDaniel is clearly an adult (even if she’s way younger than Hulk) and she could be very happy with Hogan, but dude, you married your daughter’s doppelgänger. And how do you wrap your mind around this if you’re Brooke Hogan? I know that people are supposed to be generally attracted to people who look like them, but does that also apply to their children? And how do you deal with being married to a guy who has a daughter who looks just like you? It just seems like a whole minefield of Freudian issues that no person would ever want to have to confront, and yet here they are together looking happy as clams.
9. Mary-Kate Olsen Is Married To The Significantly Older Olivier Sarkozy
Now isn’t that an adorable picture of French banker Olivier Sarkozy and his teenage daughters? No it’s not, because the girl on the left is none other than Mary-Kate Olsen, former Full House star and Sarkozy’s current wife. Mary-Kate is an adult and clearly capable of making her own decisions, and maybe vowing to stick with Sarkozy until death do they part isn’t even the worst decision she’s ever made, but good lord, do they look weird together. You’d think Mary Kate would have her pick of men. She’s pretty, successful, and was a freaking billionaire in her 20s. That’s a pretty impressive resumé. Maybe it’s because she’s done so much with her life already that she’s interested in older men, and obviously Sarkozy can’t control the makeup of his DNA or something, but the fact that his daughter (who looks about 12) is already taller than his very young looking wife just adds to the weird factor.
8. R. Kelly Dated The Much Younger Aaliyah When She Was A Teenager
R. Kelly‘s creepy, criminal behavior is now well known to pretty much the entire world, but the fact that he tied the knot with R&B singer Aaliyah in 1994 when she was only 15 years old and he was already in his mid 20s should have been a pretty obvious sign that something was way off with this weirdo. The couple denied that they had been married and tried to dodge questions about their relationship. However, Aaliyah apparently lied about her age on their marriage certificate and said she was 18 instead of 15. Aaliyah certainly has an excuse for making such a bad decision since she was so young and Kelly was a mentor that she had known since she was twelve, but the disgusting obvious conclusion about that situation is that Kelly was probably grooming her for his nastiness from the moment he met her (it would certainly make sense given his proclivities for young girls).
7. Selena Gomez Is Going Back To Immature Man-Child Justin Bieber
Just… why, Selena? Why? Dating Justin Bieber is gross enough the first time, there’s really no reason to go for a round two, and you can so obviously do better. I mean yeah, he’s young and decent-looking, but he also seems like a completely immature, insufferable little jerk, and he’s most definitely a downgrade from The Weeknd. Also this is total speculation, but it seems a little odd that this couple decided to reconcile after Selena had to deal with some very serious health issues and had to have a kidney transplant. It’s possible that the brush with danger led Selena to reconsider her life and make her want to act on feelings that she still had for Justin, but it’s also possible that Justin slipped back into his sick ex-girlfriend’s life and tried to get her back when she was at her most vulnerable. Either way, they’re totally the teen crush dream gone wrong.
6. Mel Gibson Verbally Abused His Younger Wife Oksana Grigorieva
This pair is definitely a throwback, but they’re also a very memorable one. In reality, Mel Gibson was probably on a downward spiral for a while and happened to hook up with classical musician Oksana Grigorieva during that slide, but regardless of the origins of their relationship, I’m sure most people are familiar with the end of it. Mel has gone on enough recorded rants that they might start to blend together, but his completely unhinged, manic meltdown on Grigorieva is pretty tough to forget. Aside from being littered with racial and gendered slurs, Mel says some horrifyingly degrading things to his former girlfriend and makes some genuinely frightening threats against her safety and even her life. After a scarily messy public split the couple seemed to have come to an agreement, which included Oksana having to keep her mouth shut about Mel’s crazy or else losing out on a significant chunk of her settlement in the split. But apparently it was too much for Grigorieva to handle on her own, because she decided to break her NDA and spill the beans even though it cost her a pretty penny.
5. Danny Masterson And Bijou Phillips Are Abusive Scientologists
Actor and actress couple Danny Masterson and Bijou Phillips have actually been together for ages, and mostly kept their names and their relationship out of the public eye. But after years of quiet it looks like the married couple is finally dealing with some awful publicity over their private awful behavior. Firstly, both are Scientologists, which is creepy on its own. But what’s also super creepy and disgusting is that Masterson has now been accused of multiple r*pes from former Scientologists who have said that the church of Scientology knew about what he’d done and went out of their way to cover them up at the expense of his victims. And while Bijou hasn’t done anything illegal that the public is aware of yet she’s apparently an incredibly unpleasant person to deal with. Mean Girls star Daniel Franzese worked with Bijou on a film ironically called Bully, and he says that the actress demeaned him, insulted his s*xuality and appearance, and even physically assaulted him during the filming of the movie.
4. Anna Duggar Pretends Like Her Husband Josh Isn’t Disgusting
Jesus, just look at their picture. Half a dozen cute kids, his totally creeper looking face, and her brainwashed cult eyes that look like they’re trying to escape from her head. I think that most people in the world would probably divorce their partners if they discovered that they were cheaters who had abused their own siblings as children. However, even if Anna Duggar wanted to bail on her husband she really can’t, because both she and her husband Josh ascribe to a religion that basically treats women like baby makers and doesn’t see the need to educate them beyond the 8th grade because they are just there to be fertile. Oh, and they also teach women that any of their husbands screw-ups are a result of them not being a good enough wife. But Anna apparently doesn’t want to bail on her child-abusing cheater husband because, I don’t know, he had a conversation with Mike Huckabee and it’s just what God wants her to do?
3. Kylie Jenner Was Dating The Much Older Tyga When She Was Just A Teenager
These two, are a truckload of grossness. So Tyga initially met Kylie when she was a young teen, and they met because Tyga’s current girlfriend and baby mama Blac Chyna was best friends with Kylie’s older sister Kim. And while both of them claim that the relationship didn’t start until Kylie was 18, from the outside it looks like it began (or at least Tyga was laying the groundwork for it) when she was younger. So once Kylie was legal Tyga ditched Chyna and the entire Kardashian clan turned on her, with one major exception. Rob Kardashian started spending a lot of time with her, and eventually the pair got together and Blac Chyna got pregnant with baby Dream. Kylie said a few times that she wanted to marry Tyga as soon as she turned 18, but shockingly, the relationship didn’t last. Kylie moved on quickly to Travis Scott and conceived a child with him within a few weeks of dating, which has now led Tyga to claim that the baby is actually his, not Scott’s.
2. Morgan Freeman Allegedly Hit On His Step-Granddaughter E’Dena Hines
Hey, have you ever looked at Woody Allen and thought, maybe I can give that creep a run for his money? Because rumor has it that Morgan Freeman did. He supposedly put the moves on his step-granddaughter E’Dena Hines. Freeman of course denies the allegations, but a friend of Hines said that E’Dena had told her that Morgan had put the moves on her when she was a teenager and they stopped just short of actually doing the deed. Publicly, Hines said that the claims were untrue, but there were also rumors that after Morgan decided to divorce her grandmother, she was interested in taking their relationship to a more serious and official level, but Morgan turned her down. And whether the rumors are true or false, there is certainly a very tragic end to the story. In 2015 Hines was killed by her boyfriend Lamar Davenport.
1. Mick Jagger Is 73 And Had A Child With 29-Year-Old Melanie Hamrick
Apparently it really does help to have moves like Jagger. Mick Jagger, the 73-year-old lead singer of the legendary rock band The Rolling Stones recently hooked up with a 29-year-old ballerina named Melanie Hamrick, and after a few years of dating the couple just welcomed their first child, a boy named Devereaux. And obviously Mick has more than enough money to support his new girlfriend and their child, but knocking up a twenty-something when you’re 73 seems incredibly irresponsible. I mean, the likelihood that their new child will have a significant relationship with his dad is slim since Mick is in his twilight years and rock and roll stars don’t really have a great track record with their health, and honestly, if you’re already old enough to have adult grandchildren, it’s probably time to stop making babies. Plus, despite the fact that they’ve supposedly been together since 2014, the couple is almost never seen together in public, and if you are into someone enough to reproduce with them, then you should probably feel comfortable walking down the street next to them.
- Ad Free Browsing
- Over 10,000 Videos!
- All in 1 Access
- Join For Free!