People with a lot of money and a reputation to maintain are the perfect target for blackmail and extortion. Celebrities are always in the spotlight and their image is vital to their career, so therefore they make the perfect blackmail victim. There are a lot of people out there who will take advantage of someone's trust for their own benefit, and although celebrities have a lot of security in place to protect themselves, that isn't always enough.
Blackmail is defined as "an act, often a crime, involving unjustified threats to make a gain or cause loss to another unless a demand is met. Essentially, it is coercion involving threats of physical harm, threat of criminal prosecution, or threats for the purposes of taking the person's money or property." It's something we see a lot on dramatic TV shows and movies, but it happens in real life too, and it often forces the truth into the open in order to take the power away from the blackmailer. Celebrities are even more vulnerable to blackmail because they want to keep their secrets out of the public eye for the sake of their careers.
10 David Boreanaz
The former star of Buffy the Vampire Slayer and Angel, and the current star of Bones, David Boreanaz, released a statement to People magazine in 2010 admitting that he had been unfaithful to his wife. He claimed the woman he was having an affair with asked for money. He told People, "I felt as though I was being blackmailed or there was some sort of extortion," so he decided to tell the truth himself instead of paying her off. It finally came out that his mistress was Rachel Uchitel (who was also linked to Tiger Woods), but Boreanaz managed to save his marriage and called the incident a "bonding experience" for he and his wife.
9 Bill Cosby
Bill Cosby has been accused by multiple women of rape, sexual assault, and sexual harassment, all of which he denies. Whether you believe him or not, it seems pretty clear that he has skeletons in his closet. In 1998 a woman named Autumn Jackson went to Cosby claiming to be his illegitimate daughter and the product of sexual assault. She threatened to go to the press with her story unless he paid her $40 million. Although Cosby had been giving Jackson money for her education (and to keep his affair with her mother a secret), he refused to fork over the $40 million. His lawyers contacted the FBI and Jackson was arrested and sentenced to 26 months in prison.
8 Joe Francis
Joe Francis, the founder of Girl's Gone Wild, is no stranger to criminal activity. He's been convicted of a variety of charges from tax evasion to child abuse and prostitution and forced to pay so many fines that his company went bankrupt in 2013. But in 2008, a masked man broke into Francis' house and forced him to do sexually explicit things while being videotaped. The man then attempted to extort Francis out of $500,000 for the tape. The man turned out to be Darnell Riley, a Hollywood conman who was also attempting to blackmail Paris Hilton. He was caught and sentenced to eight years in prison.
7 Oprah Winfrey
In 2006, Oprah was the target of an extortion attempt of $1.5 million. According to ABC News, a man named Keifer Bonvillain "threatened to expose tape recordings of conversations that he claimed reveal behind-the-scenes shenanigans at Winfrey's production company." He had struck up a friendship with one of Winfrey's employees and tape recorded hours of conversation which he planned to use in his tell-all book "Ruthless". Bonvillain was arrested, but the charges were dropped and he later sued Winfrey for $180 million for falsely accusing him of extortion.
6 John Stamos
In 2009, two people later identified as Allison Cross and Scott Sippola tried to blackmail John Stamos with pictures of him partying that they said would hurt his reputation. They asked for $680,000 in exchange for never making the photos public. Stamos' lawyers contacted the FBI, and the blackmailing team were arrested when they met up with an agent who was posing as a representative of Stamos.
5 Cindy Crawford
In 2009, supermodel Cindy Crawford and her husband were blackmailed with a picture of their 7-year-old daughter gagged and bound to a chair. According to the FBI the photo had been taken by a nanny during a game of cops and robbers, and was perfectly innocent. But that didn't stop the blackmailer, male model Edis Kayalar, from trying to get $100,000 to keep the picture private. Crawford's husband Rande Gerber ended up giving Kayalar $1000 for "returning" the photo, but when he demanded more, they went to the police.
4 David Letterman
In 2009, David Letterman explained on air that there was someone who was threatening to reveal his many affairs with female employees of the show if he didn't pay him off. Joe Halderman, a producer for CBS at the time, was arrested when he attempted to cash a phony check for $2 million given to him by Letterman's lawyer. Halderman pleaded guilty to attempted grand larceny in the second degree and was sentenced to 6 months in jail, 5 years of probation and 1000 hours of community service.
3 John Travolta
John Travolta and Kelly Preston's 16-year-old autistic son Jett died in 2009 after having a seizure. As if that wasn't bad enough, the ambulance driver who arrived on the scene tried to blackmail Travolta and accuse him of causing his son's death. The driver, 46-year-old Tarino Lightbourne demanded $25 million or he would take his information to the press. According to People magazine, Lightbourne was trying to use a "refusal to transport" form as evidence that Travolta caused his son's death, but in reality, there would have been no reason for that form to exist because Jett was ill enough that he'd be taken to the hospital no matter what. In the end, it was ruled a mistrial, and Travolta ended up dropping the charges.
2 Yoko Ono
Thanks to her marriage to Beatle John Lennon, Yoko Ono was one of the most recognizable, and most hated, women in the world at once point. Even her chauffeur of several years didn't seem to like her very much. Koral Karsan admitted to installing cameras in Ono's home so he could collect photos and conversations to blackmail her with. He threatened to release embarrassing pictures of her to the media if she didn't pay him $2 million. Karsan never thought he was doing anything wrong because he claimed Ono never treated him well and he deserved the money he was asking for.
1 Cameron Diaz
Photographer John Rutter threatened to release topless photos of Cameron Diaz that were taken when she was 21 years old and working as a model. He allegedly forged Diaz's signature on a release form that would allow him to use the photos how he chose. He held onto the pictures and waited until Diaz became a household name to make his move. According to him, he was offering Diaz the chance to buy the photos before he attempted to sell them to anyone else. But the court didn't see it that way. Rutter was found guilty of attempted grand theft, forgery, and perjury and faced up to 6 years in prison.