The letter is addressed to “J,” who many speculate to be John Enos, a man Madonna was dating at the time. While much of the letter explained why she and “J” could not be together, there were parts that took aim at other big-name celebrities at the time.
“I have made so many people angry that I’m being punished and basically being made to be quiet and sit in a corner while other less interesting [and] exciting people are reaping the benefits of the road I’ve paid,” she wrote, adding, “It’s so unequivocably [sic] frustrating to read that Whitney Houston has the music career I wish I had and Sharon Stone has the film career I’ll never have.”
She continued, “Not because I want to be those women, because I’d rather die but they’re so horribly mediocre and they’re always being held up as paragons of virtue and some sort of measuring stick to humiliate me.”
Madonna goes on to say that she’s “too intelligent” to play the game of being accepted but worries that “she’s lost the fight” and that her outlook on life is “black, black, black.”
To put Madonna’s mental state at that time into perspective, Houston was arguably at the peak of her artistic powers in the late ’80s and early ’90s. She had just scored the movie role of a lifetime, The Bodyguard, with Kevin Costner, and the title song, “I Will Always Love You,” catapulted the movie album to becoming the best-selling soundtrack of all time, surpassing the Bee Gees’ Saturday Night Fever.
Sharon Stone, on the other hand, had emerged as America’s favorite bad girl in theaters with movies like Basic Instinct and had superior acting skills compared to Madonna’s. The competition to be the “it” girl at the time was fierce, especially with Mariah Carey’s career also taking off like a rocket.
The bidding for the letter is expected to begin at $1K, with the ultimate price tag estimated to be around $5K when the bidding is all said and done.