In September 1996, Drew Barrymore appeared on the cover of John F. Kennedy Jr.'s George Magazine in a sequined tan cocktail dress and blonde wig, a mole painted on her left cheek. The tagline, "Happy Birthday Mr. President," was in reference to Marilyn Monroe's famous, sultry serenade to the editor's father, John F. Kennedy, at Madison Square Garden in 1962 for his forty-fifth birthday.
The image was an interesting choice for JFK Jr. considering his dad was rumored to have had an affair with Monroe, but Barrymore wasn't actually his first choice for the evocative cover.
According to a new, in-depth Esquire feature chronicling the rise and fall of George, Kennedy first asked Madonna to appear on the magazine's cover dressed as his mother, Jacqueline Kennedy Onassis.
The plan was to have fashion photographer Nick Knight shoot Madonna looking so much like Jackie O that subscribers wouldn't be able to tell it was Madonna at first glance. "Making the cover even more provocative was the fact that Kennedy was rumored to have dated Madonna before starting the magazine," writes Esquire's Kate Storey.
Kennedy wrote Madonna a note asking her to participate in the shoot, but she declined. "Dear Johnny Boy," she wrote back in a fax, "Thanks for asking me to be your mother but I’m afraid I could never do her justice. My eyebrows aren’t thick enough, for one."
The magazine, founded in 1995, had a number of A-list celebrities on its cover in addition to Barrymore, including George Clooney, Charles Barkley, Arnold Schwarzenegger, and Demi Moore. They often dressed up as famous American figures. The first issue even featured Cindy Crawford in a George Washington wig.
“He called my hotel. He reached out directly. And who’s going to say no?” Crawford told Esquire. “I trusted Herb Ritts enough to know it would be okay. But it was kind of like, I’m going to do what? Dress like George Washington? With the wig and everything?”
George folded in 2001, just eighteen months after Kennedy and his wife, Carolyn Bessette, died in a tragic plane accident. Bessette's sister, Lauren Bessette, was also in the plane with them and died.
“John died before his time,” Frank Lalli, the editor who replaced Kennedy, told Esquire's Storey. “And this magazine died before its time.”
