Frank Sinatra was a popular actor and singer, as well as a legendary entertainer in both Reno and Las Vegas during the 1950s and 1960s. So much, in fact, he was included in the holosuite program Bashir 62, a 24th century rendition of 1962. At that time, Sinatra was good friends with Dean Martin, Sammy Davis, Jr., Joey Bishop, Peter Lawford and was incorporated as a personal friend of Vic Fontaine's. Frank often served as fodder in the many stories included in Vic's programming. Sinatra was even said to be partially credited for helping John F. Kennedy win the 1960 election for President of the United States.
Vic once recalled to Odo that Frank and Dean dropped in on him once while he was playing at the Sands Hotel back in 1958. Together, the three of them took over one of the blackjack tables and dropped a combined $15,000. (DS9: "His Way")
While playing cards with his band one night, Vic recalled another story about Frank and Dino, which Vic revealed mid-story, that Frank had, as a prank, switched all the robes in the steam room they were visiting. Unbeknownst to Dino, Frank had written a descriptive word in big bold letters across the back of his robe. (DS9: "It's Only a Paper Moon")
Following the death of Jadzia Dax in 2374, Worf often visited Vic's Las Vegas Lounge to hear Vic sing Jadzia's favorite song, "All the Way". After several visits, Vic and his band began to dread Worf's arrival, as the Klingon would usually trash the lounge in a fit of rage before Vic ever finished the song. In a confrontation with Julian Bashir following his lounge's latest thrashing, Vic told him that that was the last time he would ever sing "All the Way" for Worf, no matter how much he is threatened. He then suggested that if Worf wanted to hear it again, that he should buy a Sinatra album. (DS9: "Image in the Sand")