David Letterman has been in the news for helping police foil an attempt to blackmail him, but the late-night star is hardly the first celebrity in this position. Here are a few other brazen—and mostly unsuccessful—attempts to blackmail famous people.
1. Bill Cosby
Bill Cosby may be one of television's most famous family men, but a 1997 extortion attempt tried to claim that his family was a bit bigger than anyone knew. That year, a 23-year-old woman named Autumn Jackson attempted to extort $40 million from Cosby in exchange for not telling the press she was the star's illegitimate daughter. While Cosby admitted that he had an affair with Jackson's mother and had given the woman and her daughter over $100,000 in support over the years, he flatly denied being Jackson's father. Jackson's timing probably didn't help, either; Cosby received her demand the same day Cosby's son, Ennis, was murdered.
Jackson, who was convicted along with two accomplices, received a 26-month prison sentence. An appeals court briefly overturned the sentence in 1999, but quickly reversed itself and sent her back to the clink.
2. Louie Anderson
The hefty comic became a target for blackmail after allegedly propositioning a man in a Las Vegas casino in 1993. At the time, Anderson was hosting Family Feud and starring in the cartoon Life With Louie. Rather than take a hit to his public image, Anderson shelled out $100,000 in hush money to his blackmailer, Richard John Gordon, to keep the story out of the tabloids.
Gordon got greedy in 2000, though. He came back to Anderson for another $250,000, at which point the comedian went to the cops. Gordon ended up being arrested following a high-speed chase from the LAPD, and he eventually went to prison for the extortion attempt.
3. Cameron Diaz
A note to any aspiring actresses out there: if you're planning on becoming famous, don't pose for any nude photographs. Just ask Cameron Diaz. In 1992, the young model let photographer John Rutter take nude and bondage-themed snaps of her in the hopes of making an entry into the artistic modeling market. Instead, Rutter sat on the photos until Diaz's 2003 film Charlie's Angels: Full Throttle was about to debut, at which point he made Diaz an offer: she could buy the pictures for $3.5 million, or he would sell them to magazines. Rutter claimed he had a signed release form from Diaz that allowed him to sell the pictures if he so chose.
Rather than give in, though, Diaz alerted the authorities. It turned out that Diaz's "signature" was a forgery, and Rutter was found guilty of attempted grand theft, forgery, and perjury. Although Rutter claimed that he was simply offering Diaz the right of first refusal for the salacious pics, he ended up getting a three-year jail sentence.
4. Elvis Presley
J. Edgar Hoover's FBI kept meticulous files on a lot of high-profile entertainers, including the King. When Elvis' file found its way to the public, it revealed a number of blackmail attempts, including one particularly large case from when Elvis was serving in the Army. When Elvis was stationed in Germany in 1959, he hired South African doctor Laurenz Johannes Griessel-Landau to carry out a series of skin treatments on his famous face and shoulders.
After a month, Elvis and his entourage allegedly grew tired of Griessel-Landau constantly making passes at them, so Elvis fired the dermatologist. This angered the doctor, who then threatened to reveal compromising photographs and tapes of the rock star if Elvis didn't open his wallet. Elvis held firm, though, and only gave Griessel-Landau $200 for the skin treatments and a $315 plane ticket back to London. When Griessel-Landau came back for thousands of dollars more, Elvis refused, and the blackmailer—who it turned out wasn't actually a doctor after all—eventually left the King alone.
5. Dante Gabriel Rossetti
You may not be all that familiar with Rosetti unless you paid close attention during your college English or art classes, but he was a big-name English poet, illustrator, and painter during the 19th century and was one of the founders of the Pre-Raphaelite Brotherhood. His agent, Charles Augustus Howell, wasn't quite as beloved, though, and many thought Howell was a blackmailer. If these allegations were true, they would go a long way towards explaining a particularly odd chapter in the poet Rossetti's life.
Rossetti was married to Elizabeth Siddal, a gorgeous artist and model who served as his muse. When she died unexpectedly in 1862, Rossetti made an oddly touching gesture: he put a journal containing the only copies of many of his poems in her coffin. Seven years later, Howell somehow convinced a broke, alcoholic Rossetti to dig up Siddal's coffin to retrieve the poems. The pair applied to the Home Secretary for permission, and Howell had the coffin exhumed in the middle of the night to get the journal back. It's not clear whether the notorious Howell actually blackmailed Rossetti into disturbing his wife's attempt to rest in peace, but given Howell's reputation, it seems like a reasonable suspicion. In any event, the poems flopped with critics, and Rossetti never really got over exhuming his wife's corpse.
6. Anoushka Shankar
Ravi Shankar's daughter (and Norah Jones' half-sister) Anoushka Shankar found herself in a blackmail mess of her own a few weeks ago. A Mumbai businessman allegedly hacked her email account to gain access to personal pictures, which he then offered to sell to the lovely sitar player for $100,000. The blackmailer, 28-year-old Junaid Khan, didn't get much for his trouble, though; Indian authorities arrested him on September 20.