Heidi Montag
According to then-fiancée Spencer Pratt, celebrity Heidi Montag was offered $1 million to pose in Playboy in order to show off her “new” body following reconstructive surgery. Although Montag eventually appeared in the September 2009 issue, she broke with Playboy convention and appeared with no nudity. It is unclear whether she was paid the original $1 million for her appearance.
Jennifer Aniston
After Jennifer Aniston’s revealing appearance on the cover of GQ magazine in 2008, Playboy reportedly offered the former “Friends” sitcom star $4 million to pose for the magazine. To the dismay of many Playboy fans, Aniston declined the offer, reportedly telling publisher Hugh Hefner that, “ GQ was art, but Playboy is sex.”
Ashlee Simpson
Another huge offer made by Playboy was to recording artist Ashlee Simpson, to the tune of $4 million, according to TMZ. Like Aniston, Simpson, the younger sister of singer Jessica Simpson, turned down a $4 million figure, demonstrating that big paychecks alone aren’t always the best way to secure a photo shoot.
Foxy Brown
According to the New York Post, rapper Foxy Brown said in July 2011 that she was contemplating a $2 million offer to pose for Playboy. Brown’s music career has been hindered by everything from hearing loss to criminal convictions, and a $2 million paycheck would signal a reversal of fortune for the artist, who pled “not guilty” to a felony charge in 2010.
Lindsay Lohan
According to reports from TMZ, Lindsay Lohan recently finalized a deal for “almost a million dollars” to appear in the magazine. When contacted by CNBC.com, a Playboy magazine spokesperson would not comment on the report. TMZ says that Lohan initially balked at an offer of $750,000, but eventually reached a deal. It is unclear when Lohan’s photos will appear in the magazine.
Melissa Joan Hart
Another celebrity who was reportedly offered a huge paycheck to appear in Playboy was actress Melissa Joan Hart. According to reports, Hart was offered a cool $1 million to pose for the magazine during her time on the hit TV show “Sabrina the Teenage Witch.” Although she said she was tempted to “shed her good girl image,” Hart eventually turned down Hefner’s offer after a less revealing photo shoot with Maxim earlier in her career made her uncomfortable.
Denise Richards and Pamela Anderson
Neither Pamela Anderson nor Denise Richards are new to Playboy, with Anderson appearing a record 13 times and Richards gracing the front cover in 2004. The duo, who had become friends while working on the movie “Blonde and Blonder” in 2007, reportedly had been offered $1 million to appear together in an issue. This proposal never came to fruition, however, and Playboy has declined to comment on the offers it makes. In Anderson's most recent Playboy appearance, she was reportedly paid $25,000, which she donated to charity.
Rachel Hunter
Another high-priced offer from Playboy was made to supermodel and actress Rachel Hunter, who reportedly had been sought by the magazine since she was 17. Hunter eventually appeared in the April 2004 issue at the age of 35, after reports surfaced that she had been offered $1.8 million to pose for the magazine.
