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The Rat Pack

Las Vegas has always been an almost surreal place, and as a source of pop culture entertainment it is unrivaled. Entertainers have always flocked to Vegas, and it continues to be the barometer of who's cool and “in” at the moment. The city was a popular destination; there was plenty of money to be made, there were many ways to liberally indulge vices, and many got a vicarious thrill from hobnobbing with the hoodlum element. Perhaps no entertainer was more enamored of the Mafia and its brethren than Frank Sinatra.

Jack on the Rocks

Sinatra had an association with the mob going back to his early days as a saloon singer in Hoboken. From the 1920s to the 1940s almost every singer and comic had to contend with the Mafia, since the mob has a long history of involvement in the clubs and venues where they perform. Most performers of that generation accepted this fact and for the most part got along with their employers. Sinatra, by all reports, had a schoolboy romanticism of gangsters. And when he was down on his luck and his career was in a slump, it was his mob friends who still paid him to sing in their saloons. Sinatra was nothing if not loyal to his friends, and when the Vegas party was in full swing, he was a regular fixture at the Sands and Dunes, along with his cohorts, Dean Martin, Peter Lawford, Sammy Davis Jr., and Joey Bishop. Together they created a slice of pop culture lore that continues to fascinate people everywhere.

The Chairman

Sinatra, who was given the option to purchase 9 percent of the Sands Hotel by his mob friends, performed there often, always packing the house. And a sold-out crowd of Sinatra fans inevitably wandered over to the slot machines and gambling tables. Sinatra got it in his head to make a movie in Las Vegas. This became the 1960 film Ocean's Eleven, more memorable as a time capsule of an epoch than as a cinematic masterpiece.

The Rat Pack filmed Ocean's Eleven by day and performed at the Sands by night. The show was called “the Summit,” named for the Cold War conferences between the United States and the former Soviet Union.

Did Frank Sinatra ever play a mobster in a movie?

Frank played a gambler in Guys and Dolls, a mob boss in Robin and the Seven Hoods, and a satire of his “Mafia” personality in the otherwise forgettable Cannonball Run II. In fact, Sinatra played cops far more than he played bad guys.

Progressive Retro

One positive thing Old Blue Eyes did was help break the race barrier in Las Vegas. Black performers were not allowed to stay in rooms at the hotels in which they performed to sold-out crowds and standing ovations. Velvet-voiced crooner Nat King Cole was instructed not to make direct eye contact with the swooning fur-adorned and bejeweled ladies in the audience. Black performers had to withdraw to a shantytown on the wrong side of the tracks at the end of the show.

In the ultimate example of “strange bedfellows,” many of the workers, pit bosses, and managerial types in the Mafia-owned casinos were Mormons. The faithful of the Latter-day Saints do not drink alcohol, coffee, or gamble. But they are not forbidden to work in casinos. It was a strange alliance that served the Mafia well.

One day Sinatra announced that he would not go on unless his chum Sammy could stay at the Sands and play blackjack at the tables and swim in the pool. Sinatra helped pave the way for integration in Las Vegas. The Mafia did not fret much either way. Green was the only color that truly inflamed their larcenous hearts.

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  4. The Rat Pack
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