8. Madonna’s Application for an Apartment at the San Remo Was Rejected

The San Remo has long been a celebrity favorite, with a long list of notable past and present residents, including Dustin Hoffman, Steve Martin, Diane Keaton, Bono and many others. One celebrity who wasn’t able to secure an apartment in this star-studded building was Madonna, who applied to buy a $1.2 million co-op unit in 1986.

At the time, she had yet to reinvent herself as a “model mother and children’s book author,” according to author Richard Alleman. Perhaps in an effort to win over the board members, Madonna reportedly showed up for an in-person meeting, dressed in a basic black dress, wearing a strand of pearls and two gold crucifixes around her neck.

Unfortunately, that apparently wasn’t enough. Diane Keaton, who was a member of the building’s co-op board, was the only person to not reject her application.

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