Even though she outfitted the apartment, for reasons unknown, with an authentic Apple Store glass staircase, Long Island car insurance mogul Penny Hart wasn't able to find anyone willing to pay $7.7 million for Frank Sinatra's former penthouse. Now the listing has returned, furnished and $2.1 million cheaper, asking $5.595 million. Whether or not the addition of tables and couches makes the place more appealing is up for debate (if anything, they somehow make the gaudy inlaid floors even more startling), but the lower price tag should definitely help, as should the apartment's history. Originally owned and designed by Sinatra himself, it was partied in by the likes of John F. Kennedy, Marilyn Monroe, and Sammy Davis Jr. (Davis purportedly liked to stand on the terrace and throw champagne glasses onto the FDR Drive). It was later owned by Andy Warhol's doctor Denton Cox, and, after his death, sold for $2.5 million to Hart, who renovated it, aggressively.