15 Famous Female Hotties Landed By Creepy Dudes

There are a lot of different types of couples in the world. There are some that involve people of the same sex and others that include people of opposite sexes. There are still others that are of a similar age to one another and some that were born in entirely different generations. There are some that are of the same race and others that are multicultural. Despite the many different iterations that are out there, one thing that remains true far more often that not is that most of us are involved with people that are similar to us in the level of our looks. Sure, we all know that each couple tends to have someone who is slumming it a little and another that is a little bit out of their league but the vast majority of people are with someone that makes sense outwardly. That is why it is so remarkable when that doesn’t hold true.

When it comes to finding a mate in this world it oftentimes seems as though there is no group that has it easier than beautiful women. Sure, we’ve all seen interviews with models that swear that people are too afraid to approach them so they end up alone but we typically see them months later on the arm of a hunk of some sort. As a result, we always expect to see attractive women end up with the pick of the litter but when they instead end up dating someone that seems creepy, it is simply awe-inspiring. That is because guys who are off-putting like that appear to have it the worst of anybody. Coming to that realization is what inspired us to put together this list of the fifteen creepiest dudes who landed the hottest girlfriends.

In order for a couple to be considered for inclusion here, it needs to involve a man and a woman, not because we are against same-sex couples, we celebrate them, but due to the concept of the article. It doesn’t matter if the people in the relationship are still together as long it is clear that at one time they were. We also aren’t limiting ourselves to people who are alive at the time of this writing. On top of that, it needs to include a lady who the vast majority of people would see as hot, even if beauty is in the eye of the beholder. Finally, the man in the relationship needs to come off as creepy in one manner or another. That said, we want to make it clear that we don’t know any of these people personally, so the woman may be nasty and unattractive in person and the man personable and charismatic.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Avril Lavigne & Chad Kroeger

The lead singer of the Canadian band Nickelback, which is one of the most celebrated and reviled groups in modern music history, Chad Kroeger has been the subject of a lot of debate over the years. If you question the degree to which Chad and his bandmates are disliked by some, a Canadian town called Kensington had to apologize after saying they would use their music to punish drunk drivers. An interesting turn of events as Chad had been convicted of DUI himself years earlier, he must have come to terms with the hate by now. That is especially true after years of having one of the creepiest hairdos in the music industry, he sported a greasy long look for far too many years. Marrying fellow Canadian musician Avril Lavigne in 2013, his wife wasn’t the stereotypical beauty but there is no question that she possessed an incredible body and was the apple of a lot of eyes.

14 Elisabetta Gregoraci & Flavio Briatore

For those of you who are unaware of who Elisabetta Gregoraci is, let us introduce you to this Italian beauty. A model and television personality over there, she was the subject of a lot of controversy at one point after it came to light that she had offered up sexual favors in order to get work. In return, she received a job as a showgirl for the Italian national public television company RAI. Once the controversy was revealed she left RAI but in quite the twist went to work for the Italian Prime Minister Silvio Berlusconi who was the owner of a media company as a hostess for the show Buona Domenica. Included on this list because of the fact that she married Flavio Briatore, a Formula One manager who is nearly thirty years her senior, the age difference isn’t the only thing that makes him a creep. He is also a figure of controversy as he was involved in race fixing at the 2008 Singapore Grand Prix which is a very slimy move.

13 Helena Bonham Carter & Tim Burton

One of the best-known movie directors alive, when Tim Burton makes a movie chances are that film buffs would recognize his trademark style even if he took his name off of it. A talented man who seems to delight in a gothic motif, there are several creepy people listed here that may not like that designation but we could easily see Tim enjoying that perception. When it comes to his former partner and mother of his two children, Helena Bonham Carter seems to share his taste for the macabre which has led some to underestimate her looks. Oftentimes seen in Tim’s films, she transforms her looks for a lot of those roles but we shouldn’t let that cloud our minds when it comes to how attractive she truly is. After all, even when she played a messed up character in the movie Fight Club she managed to be desirable despite the fact that she was kind of frightening too.

12 Beth Ostrosky & Howard Stern

Howard Stern has the type of fanbase that any celebrity would kill to have. Supremely loyal to him, many of them listen to every bit of content that he offers up and take his word as gospel which has helped his claim of being “The King of All Media” ring true. Still, at the end of the day, he is still a stick thin dude who horndogs after every beautiful woman who appears on his show and has a history of paying people to do perverse things on his show. On the other hand, his wife since 2008, Beth Ostrosky Stern is an author, animal rights activist, model, and actress. A statuesque blonde with a body to die for, she has appeared on lists like FHM’s Sexiest Women of the Year and AskMen.com’s Most Desirable Women in the past.

11 Paula Patton & Robin Thicke

The lead performer on a track that was the song of the summer in 2013, “Blurred Lines” led to Robin Thicke becoming an international music star who seemed to have it all going for him. A good looking dude with a wife millions of people lusted after and a successful career, it was all his to lose and it seems as though he has done just that. First seeing some controversy for his off-putting duet with Miley Cyrus, it was when he was pictured feeling up a fan that things really began to fall apart. Losing Paula to divorce after a decade together, he released music that pleaded with her to return and after his previous misdeeds, it was hard to feel sorry for him. Coming off like an obsessed ex that nobody would want to deal with, the whole thing was rather gross for the world to witness. We guess if we lost a woman as exquisite as Paula we may act a little crazy too.

10 Holly Madison & Criss Angel

Via zimbio.com

A woman that came to prominence through starring on a “reality” show called The Girls Next Door, it focused on her relationship with her “boyfriend” Hugh Hefner, and the women she shared him with. A ratings juggernaut because it gave the world a glimpse of the unique life Hef and his bunnies led, it also owed a great deal of its success to the fact that the women on the show were extremely hot. Arguably the most attractive member of the cast, Holly is a woman that posed nude for Playboy more than once and was given the prime role on the show. Going on to date a magician who would star in the show Criss Angel Mindfreak, her new man was a decent looking fellow but after years of trying so hard to be edgy, the dude just seems creepy. In fact, he is seen so poorly by a lot of people that he has routinely been called a douchebag for years now, including having an episode of the show Supernatural name an episode 'Criss Angel Is a Douche Bag'.

9 Lisa Marie Presley & Michael Jackson

Via Pinterest.com

In the history of music, there are a few performers who managed to stand head and shoulders above the competition when it comes to their sales and perception. Elvis, Madonna, and The Beatles immediately come to mind but Michael Jackson certainly deserves to be considered of a similar caliber to those amazing acts. Breaking records and selling albums during his career, many of his tunes will go down in history because of how catchy and memorable they remain even now, several years after he passed on. Previously married to Lisa Marie Presley, the daughter of another music megastar, they were the talk of the town, and the moment they kissed in front of millions of people at an awards show is unforgettable. Blessed with her father’s genes, she had a very distinctive face in her prime and was quite fit and sexy in her own right.

8 Evan Rachel Wood & Marilyn Manson

Via nydailynews.com

We mentioned earlier that we thought Tim Burton might enjoy being called creepy but there is no question in our minds that Marilyn Manson would. A singer that made a career for himself partially through the shocking nature of his music and stage persona, he had a hit song called “Antichrist Superstar” and that title didn’t seem far off the mark for some. We’d continue to explain what makes him such a creepy dude but anyone who looks at him will probably be able to surmise that themselves which is why we we're shocked he landed Evan Rachel Wood. An immensely talented actress, she made a name for herself in movies like Thirteen, King of California, Across the Universe, and The Wrestler on top of the show Westworld. A beauty for the ages, she has an edge to her that is hot as hell as well as having the type of looks that could have inspired the most talented poets to spend years working to capture it in words.

7 Shannon Elizabeth & Joseph D. Reitman

An actress that is best remembered for playing a pivotal part in the American Pie franchise, as Nadia she was an exchange student who served as fantasy fodder for the movie’s main character, Jim. The focus of the film’s sexiest scene, when she got changed in his room and the audience got a view of her breasts, any question of her beauty that may have existed previously completely disappeared. Going on to appear in movies like Scary Movie, Jay and Silent Bob Strike Back, Thir13en Ghosts, and Love Actually in which she cameoed, she broke the mold of actresses cast as eye candy alone. Also known for competing on Dancing with the Stars, she would date her partner on the show which seemed much more fitting than the man she wed in 2002. Married to Joseph D. Reitman until 2005, as an actor he seemed much more likely to play a stalker than a leading man.

6 Crystal & Hugh Hefner

There have been many men over the years that have said that Hugh Hefner is their hero and for a time that made some sense. An older gentleman that was flanked by a harem of beautiful women, it seemed as though he had the world on a string as evidenced by the fact that the guy was able to walk around everywhere in a robe. That is the type of life that a lot of people fantasize about but as he gets older and stories surface that shine a light on some of the aspects of his life, it just seems sadder and creepier as the years pass on. Married to his third wife, Crystal Hefner is a former Playmate of the Month and looks great with her clothes on too, which is what made her the obvious choice to partner him with on this list.

5 Mary-Kate Olsen & Olivier Sarkozy

Via intouchweekly.com

Mary-Kate Olsen and her twin sister came to prominence due to their shared role on Full House where they quickly became quite possibly the most popular cast members. Growing up to create an empire for themselves, they were the stars of movies, designed clothes, and turned themselves into huge stars in a long list of ways. An attractive young woman, Mary-Kate has eschewed the spotlight to a large degree as an adult but that hasn’t stopped her from being the subject of discussion due in large part to her relationship status. Married to a man seventeen years her senior, Olivier Sarkozy, who is also the half-brother of French President Nicolas Sarkozy, the pictures of them in public venues like basketball games are cringeworthy.

4 Brittany Murphy & Simon Monjack

An actress who showed off her impressive skills as part of Clueless’ cast, she played a supporting role but stole the show in a lot of people’s minds. Going on to play more dramatic roles in movies like Girl Interrupted, 8 Mile, Riding in Cars with Boys, and Sin City this helped cement her reputation as a talented performer. Also quite adept at comedy, she also provided her voice for the animated series King of the Hill and played roles in movies like Drop Dead Gorgeous, Just Married, and Little Black Book. Having previously dated Ashton Kutcher, the world was surprised when she became involved with and eventually married Simon Monjack, who wasn’t a known entity and seemed to always hover over her.

3 Courtney Stodden & Doug Hutchison

Prior to marrying a sixteen-year-old girl when he was thirty-four years older than her, most people wouldn’t be able to name Doug Hutchison if their lives depended on it. Someone who had played creepy people in the past, most notably in The Green Mile, he was good at his job but now we can only see him as the sicko that married a person that was a child in comparison to him. Courtney Stodden for her part has garnered headlines outside of their marriage too due to her buxom body that a lot of people are attracted to now that she is a woman in her early twenties.

2 Melania & Donald Trump

We realize full well that referring to the President of the United States as a creep isn’t very respectful and for anyone who feels insulted by that we apologize, but facts are facts. Somebody who has been accused of sexual assault by a long list of women, he was also recorded boasting to Billy Bush about how his celebrity position allows him to do what he wants to women. While that has been referred to as “locker room talk” there are a lot of guys who can tell you they’ve never been subjected to discussion like that. Then there is the First Lady who has been the subject of her own controversies in the past, but what woman in her position hasn’t been. No matter what you think of her, there is no denying that she is an attractive woman. A former model who appeared in the 2000 edition of the Sports Illustrated Swimsuit Issue, one of the most coveted gigs in that industry, she can definitely be called hot.

1 Denise Richards & Charlie Sheen

When the movie Wild Things came out, the main cast consisted of celebrities like Kevin Bacon, Matt Dillon and Neve Campbell, alongside a relative newcomer named Denise Richards. Once the world got a look at her sexy performance and outrageous body a star was born and in the years since she has proven that no matter her age she is a gorgeous gal. Formerly married to Charlie Sheen, a man who became a star in the eighties and was the star of a successful series as recently as 2014, he has shown true staying power. That is incredibly impressive, especially in light of the long list of controversies he has been embroiled in, the highlights of which is what makes us call him creepy. A confirmed customer of a prostitution ring, he has also acted extremely erratically, and at one point surrounded himself with two girlfriends he called his goddesses.

Source: cbc, ew, huffingtonpost, esquire, washingtonpost

More in Entertainment