Hollywood is pretty much known for its ambivalence over the sexual habits of its stars. With so many celebrities rising to fame through sex tapes and backroom casting sessions, it has become widely acceptable in the entertainment industry for celebrities to sleep around and yet still be able to continue on to fame. Many celebrity couples are a variable mix and match game with connecting partners that intersect with the "Who’s Who" in Hollywood.
However, there are times when the relationships created between the sheets sometimes negatively affect the professional careers of those in Hollywood. While the public started off with an obsessive fascination with the relationship between Jennifer Lopez and Ben Affleck, the pairing ultimately became a hindrance to their careers. Spawning the “Bennifer” nickname, the pair became a cringe-worthy tabloid staple rather than a dynamic duo people rooted for to walk down the aisle. Ultimately they called off their engagement, and both of them have since tried desperately to distance themselves from their embarrassing Gigli past.
The fact that a romantic relationship between an A-list Academy Award winning actor and a bootylicious entertainer can cause such career havoc shows how public perception can be a fickle thing. While some celebrities have managed to change their reputations through hit films and upgraded relationships, not everyone has been able to escape their seedy sexual past. Check out our list of 15 celebrities that have been overshadowed by their sexual escapades, and see how some mistakes and blunders simply can’t be overlooked.
15 Kendra Wilkinson
Although Kendra Wilkinson received a mildly successful reality show on her own, audiences still remember her as the 19-year-old Playboy model made famous through The Girls Next Door. As just one of the three girlfriends to the elderly Hugh Hefner, she was forever seen as just another gold digging opportunist trying to claim her 15 minutes of fame. She famously opened up about the sexual relationship between her and Hefner, claiming “it wasn’t a pleasant experience” and that she frequently used alcohol and drugs just to get through it. Even through all the public drama, she was able to maintain a friendly relationship with Hefner, and even married her husband, Hank Baskett, at the Playboy mansion.
14 Kim Kardashian
Kim Kardashian has been able to build an empire with the brand she has created over the years. A successful partnership with Sears for women’s clothing, a reality television show with stellar ratings, and even a booming app that lets fans play the role of herself to reach fame through their phone or tablets; it seems like she can add savvy businesswoman to her long list of accolades. Unfortunately, a sex tape with Ray J is also on that list, and the public never lets her forget it. Not only does the Hollywood Walk of Fame disregard her success, but it seems that all of Hollywood does also. Since you must be nominated to get a star on the Walk of Fame, other celebrities can’t get past the fact that Kim rose to success by laying on her back.
13 Arnold Schwarzenegger
When Arnold Schwarzenegger was in his heyday as a film star, there were numerous accusations circulating about his horn-dog ways on and off the set. Claims of him grabbing female extras on set and being vulgar around his female cast members seemed to be the norm during an Arnold Schwarzenegger film. However, the world thought maybe he’d change once he married Maria Shriver. She seemed to legitimize him, and definitely helped in pursuing his political career, but it didn’t take long before the old Arnold had reared its ugly head. Not only had Arnold cheated on Maria with another woman, but he cheated on her with their longtime maid no less. Mildred Baena (who will live on in infamy as "Mildred the Maid") had been having an affair with Arnold, and even gave birth to their son. While Arnold’s marriage to Maria ultimately came to an end, tabloids still follow around the love child of Arnold and Mildred and note how much he looks like his father.
12 Gavin Rossdale
As the lead singer of Bush, Gavin Rossdale seemed like the perfect man for the free-spirited rocker, Gwen Stefani. The couple had a lavish wedding and a marriage that spawned three children. But the couple went through a few obstacles along the way. Reports came out about a former relationship Gavin allegedly had with a cross-dressing man named Marilyn. After a few denials and admissions, the world was a bit surprised that Gwen managed to overlook this revelation and continue on with the marriage. However, things came to a head when Gavin was found to be having an affair with their longtime nanny (who incidentally, looks a lot like a younger version of Gwen).
11 Bill Cosby
Once thought of as one of the greatest standup comedians of all time and beloved television father, Bill Cosby was the pinochle of family-friendly fun throughout the '80s and '90s. Women sought out to find their Heathcliff Huxtable that would be the perfect husband and father, not knowing all the seedy details that occurred behind closed doors. When the first sexual allegations came forward, many people thought of it as a money-seeking woman trying to defame a beloved celebrity. However, when more and more women started coming forward with the same horrifying details of being drugged and sexually assaulted, it became harder to deny the type of man he truly was. The Cosby Show has since been canceled from reruns on television, and public perception of this "Pudding Pop" celebrity has turned to disgust and disbelief.
10 Woody Allen
While Woody Allen is still revered as a pioneer in film, many find it difficult to forget about the sexual escapades from his past. When Woody Allen married Mia Farrow, it seemed like he had tapped into just the right mix of separate-togetherness that was the catalyst to a happy marriage. However, when she discovered nude photos of her adopted daughter, Soon-Yi Previn, the world got a better glimpse at what was really going on behind closed doors. Woody Allen went on to marry Soon-Yi, but it never became a legitimate relationship in the eyes of the public. This creepy perception of Woody Allen was only further enhanced when new allegations of sexual abuse came out regarding his relationship with Dylan Farrow when she was just 7-years-old.
9 R. Kelly
Don’t let this “Step In The Name Of Love” artist fool you. When it comes to sexual deviance, R. Kelly has it in spades. Not only does he have two separate underage marriages stemming back from 1994 with his then-protégé Aaliyah, but he also was alleged to have sexual relations with another underage girl in a shocking sex tape. While he was ultimately acquitted of all charges in the case, it took six years away from his professional career. The prosecution couldn’t definitively prove that he was indeed the man in the tape, or that the girl wasn’t an appropriately-aged prostitute as the defense contested. However, audiences couldn’t seem to get over the fact that the man looked identical to R. Kelly, despite missing a distinctive mole on his back, and of course there’s the golden shower incident depicted in the video.
8 Paris Hilton
Becoming famous for being famous, Paris Hilton seemed to have it all when she was first introduced to audiences in the reality show, The Simple Life. She was beautiful, thin, and an heiress to the Hilton dynasty. What she also had was a newly leaked sex tape with then-boyfriend Rick Salomon, which has now gone down in infamy. While other celebrity sex tapes focus on the intimate relationship between both parties, hers was received more for its comical content. Shot with a distorted green-lit night vision look, the couple looks almost alien during their steamy romp. On top of the strangely shot video, Paris stops abruptly to answer her phone during the session, and begins talking nonchalantly with her mother. With one of the most popular celebrity sex tapes of all time, it will definitely be awhile before the public starts to forget about 1 Night in Paris.
7 Padma Lakshmi
Like many women in Hollywood, Padma Lakshmi has been the focus of numerous tabloids prying into her personal life. The rocky marriage and divorce with Salman Rushdie caused people to wonder who her next beau would be. The Top Chef host stirred up a media storm when she became pregnant in 2009, and didn’t know who the baby’s father was. A bitter custody battle ensued (including a DNA test), and the child was found out to be from her ex-boyfriend, Adam Dell.
Padma opened up to Matt Lauer in an interview where she was asked about the fact that she was open about sleeping with more than one man at a time. She said, “I probably shouldn’t have been with anybody and just taken the time I needed for myself but I was presented with two very different, very interesting men and men do it all the time. I chose to do it. I was open with the men involved.” While it is true that many men choose to sleep around without any commitments, the public often turns on women who try and engage in the same type of behavior. While she seems to have moved on from this experience, even writing a book about it, she is still known to many as the woman who didn’t even know who got her pregnant.
6 Charlie Sheen
While some celebrities have one or two sexual debacles in their past, Charlie Sheen has far more than anyone could count. Listed as a celebrity client in Heidi Fleiss’s infamous Black Book, it was no secret that he partook in activities with those in the sex industry. After a few failed marriages and extended drug use, he became a bit more open about his sexual escapades. He started posting profiles online with the bio of being “an A-list actor,” and often had rowdy hotel parties with various adult film actresses. Nowadays, the biggest Charlie Sheen headline involves his revelation of being HIV positive and that he is involved in lawsuits by women who claim they were never told about his HIV status.
5 January Jones
First thought of as Hollywood’s next “It” girl, things quickly changed for January Jones when rumors started circulating about her overactive sex life. The list of past relationships are a Who’s Who in Hollywood ranging from television to film, and include some partners that were already in relationships or married. The most infamous pairing was with Bobby Flay, when he was still married. She famously got into a hit and run incident where she inexplicably called Bobby Flay to presumably help her out of that jam. While there have been numerous photos of January Jones with various men in Hollywood, the real proof of her devious past is the fact that she refuses to reveal the name of the father of her baby. When turning up pregnant on the red carpet, everyone was abuzz, but she kept the father’s name secret and continues to do so.
4 Leonardo DiCaprio
Every era in Hollywood seems to have their own special group of celebrities that are part of the “In crowd.” From the Rat Pack to the Brat Pack, young Hollywood is known for partying hard and sleeping around. While it never really affected Frank Sinatra or Rob Lowe, Hollywood is starting to change a bit when it comes to the respect given to actors based on their personal life choices. Coined the “Wolf Pack” or the “Pu**y Posse,” Leonardo DiCaprio and his group of friends have made quite a name for themselves in Hollywood. While everyone can agree that he is a super talented actor, the constant partying and model hopping has become a feature that has often overshadowed his work. In fact, many people attribute this to why he hasn’t won an Academy Award until recently. Rather than taking another model as his “Plus 1,” DiCaprio wound up taking his Mom to the Oscars (which many people thought was a calculated tactic to try and take away from the playboy image that has kept him back for so many years).
3 Pamela Anderson
While Pamela Anderson wasn’t exactly the first celebrity to come out with a sex tape, but she was definitely one of the leaders in making this a turning point for a career in Hollywood. Her sex tape with Tommy Lee became a huge success, and he even released a parody music video that referenced the tape. Rather than trying to distance herself from this, she went on to add a few more notches in her sexual bedpost. Showing that she definitely has a type, she can be romantically linked to other grunge-looking guys like Kid Rock and Rick Salomon. She has tried to revamp her look in recent years to reflect her age and the fact that she’s a mother, but the public will always view her in a certain way due to her seedy sexual past.
2 Naomi Campbell
With her career revived through her new role on the hit television show, Empire, Naomi Campbell is proving that she is more than just a supermodel. However, it’s the antics in her personal life that have made headlines throughout the years. Her list of past partners includes a wide variety of men including Mike Tyson and Robert De Niro (which clearly shows she doesn’t have a type). While many of these relationships have been volatile, it’s the latest breakup that has had people talking. International businessman Vladislav Doronin dated Naomi Campbell in what only can be described as an ultra lavish and opulent relationship, including trips around the world and yachting vacations. The only hiccup to this relationship was the fact that he was still married during the entire relationship. In some instances, Vladislav’s wife was photographed on these trips with them, which either makes it better than being the secret mistress or flat out weird for traditionalists.
1 Tom Sizemore
Best known for his tough guy roles in Hollywood, Tom Sizemore has played parts in numerous iconic films like Saving Private Ryan and Born on the Fourth of July. However, things started to go downhill once he started battling addiction, even entering Celebrity Rehab. In October 2005, Tom Sizemore decided to take full advantage of his name by going into the adult film industry. Collaborating with Vivid Entertainment, The Tom Sizemore Sex Scandal tape was released, and included a collage of him having sex with multiple women. He's alleged to have had sex with Paris Hilton, but it wasn’t shown on the tape and Paris Hilton adamantly denied the allegations.