Ocean’s Eleven: The Rat Pack at Work and Play

Peter Lawford heard the story first. He told it to Frank Sinatra. Sinatra bought the rights (giving Lawford a piece) and hired the screenwriters, Harry Brown and Charles Lederer, to develop it. The tale became Ocean’s Eleven, the story of World War II army buddies getting together for one last grand assault — the simultaneous robberies of four Las Vegas casinos.

The Rat Pack, in 1960, were golden. The casino bosses on the Las Vegas Strip were especially happy to see them. They filled up the hotels and brought in the high rollers. According to Nick Tosches in Dino, his biography of Dean Martin, they attracted fans “who lived vicariously through them, to whom the imitation of cool took on the religiosity of the Renaissance ideal of imitatio Christi.” For the casino owners, that meant a lot of cold, hard cash.

The Cathedral in the Sun

If the Rat Pack were the high priests of cool, then the Sands, that “place in the sun” was their cathedral. For the purposes of Ocean’s Eleven, the Sands became base camp.

The five of them — Sinatra, Martin, Lawford, Sammy Davis, Jr., and Joey Bishop — made a deal with Jack Entratter, the president of the Sands. During the run of the shoot, they would put on two shows nightly, seven days a week. The shows would not be predictable.

Sometimes only one of them would perform, sometimes two or three, sometimes all five. Some nights there would be guest performers; sometimes the only female Rat Pack member, Shirley MacLaine would appear, occasionally Milton Berle. After the shows, they would party until dawn. By then, it was time to get back to the set, and a different kind of party. Angie Dickinson, who played Sinatra’s wife in the film, remembered, “You’d have to look hard to find a camera to prove to you that they weren’t playing. They really had fun together. The director [Lewis Milestone of All Quiet on the Western Front fame] was very easy. He knew exactly who was signing his check.”

Las Vegas as the Ultimate Playground

The dream Bugsy Siegel had back in the ’40s, when he built the Flamingo, the beachhead on the Strip, had come true. Las Vegas was a destination, a playground for adults. The three months the Rat Pack spent filming Ocean’s Eleven there confirmed it. The place was packed. The mobsters who built the town and retained an interest, people like Sinatra’s friend from Chicago, Sam Giancana, found themselves rubbing shoulders with celebrities and politicians.

Hobnobbing with Politics

Among the politicians in town while the Rat Pack filmed Ocean’s Eleven was a young senator from Massachusetts who happened to be Peter Lawford’s brother-in-law and who happened to be running for president: John F. Kennedy. Kennedy was already using one of Sinatra’s hits, “High Hopes,” as his campaign theme song.

The Rat Pack would later sing the “Star Spangled Banner” to open the 1960 Democratic National Convention (to the protests of the delegates from Mississippi, who objected to the presence of Sammy Davis, Jr. on stage). In between the Ocean’s Eleven shoot and the convention, the Pack grew tight with the senator, campaigning for him, and partying with him. The candidate particularly entranced Sinatra, who loved power.

Leading Through Charisma and Courage

Back on the set of Ocean’s Eleven, Sinatra was demonstrating his devotion to power in a different way. Danny Ocean is the embodiment of Sinatra as the leader of the Rat Pack, the guy who comes from the wrong side of the tracks, who leads through a combination of charisma and courage. This is made starkly clear in Ocean’s relationship to Peter Lawford’s Jimmy Foster in the film. During their World War II service, Foster was the officer, the lieutenant; Ocean, the non-com, the sergeant. Foster and the other men all defer to Ocean, though, and it is clear that this has always been their relationship.

Blending the Public and Private

Ocean’s Eleven does not have characters so much as it has types. All the types just happen to match the public personae of the various members of the Rat Pack.

Besides Sinatra playing it slightly roguish and totally cool, there is Dean Martin. Martin’s Sam Harmon embodies a different kind of cool than Sinatra; he is the singing, jovial pal who sees right through the robbery plan, telling Ocean, “The percentage is always with the house.” Harmon nevertheless goes along with the scheme, putting camaraderie before common sense.

There’s an exchange between Martin and MacLaine, playing a drunken bystander, in a parking lot that distills the essence of the Rat Pack. Harmon turns on charm, wishing her a happy New Year. She objects. He wants to know who he has to be to wish her a happy new year. She says Ricky Nelson. He tells her, “I used to be Ricky Nelson. I’m Perry Como now.” Identifying the difference between the Rat Pack and that particular sedate crooner, she replies, “No, you’re not — you move.”

Lawford plays Jimmy Foster, a charming and spoiled rich boy, which — with him being Jack Kennedy’s brother-in-law and having family access to the Kennedy power base — might be how he seemed to his fellow Rat Packers. (This he would pay dearly for a few years hence, when Sinatra banished Lawford from the Pack forever. When Sinatra’s relationship with President Kennedy cooled, allegedly because of Sinatra’s mob ties, somehow Sinatra managed to blame Lawford.) But given his family connections, his father-in-law Joe Kennedy’s unsavory reputation and the later rumors of how Jack might have won the election with an assist from Sinatra’s gangster pal Sam Giancana, Foster’s plan for his share of the money is telling. He intends to turn “money into power … think I’ll buy some votes and go into politics. Pay off your own party. Settle for an appointment. Do you have any idea how much you can steal if it was something like Commissioner of Indian Affairs?”

Sammy Davis, Jr. as Josh Howard is more of a cipher. Davis was a full member of the Pack and he always got equal billing with Sinatra and Martin, but his parts were invariably smaller. In those nascent days of the civil rights movement, the movies were as segregated as other American institutions. The Rat Pack and their writers were simply too timid to fan the flames of potential controversy by expanding Davis’ roles. To compensate for never getting the girl, Davis generally had to make do with a show-stopping number. Ocean’s Eleven is no different as Martin gets the necking scene in the parking lot, while Davis memorably enlivens the film with the theme song, “Ee-o-eleven.”

A Big Boy’s Sandbox

Ocean’s Eleven represents the Rat Pack at their peak, though it is not the best work for any of them. Their parts would always far surpass their whole. Ocean’s Eleven captures them, though, at the apex of their fame, convinced that their work was really play and that Las Vegas was really just a big boy’s sandbox. The world Ocean’s Eleven presents is not the world as it was, but the world as the Rat Pack saw it, as they spent their lives in recording studios, nightclubs, and the latest fast cars.

At the end of Ocean’s Eleven, Sammy Davis, Jr. sings, “Show me a man without a dream and I’ll show you a man that’s dead, real dead.” Frank Sinatra and the Rat Pack had a dream in 1960, a dream where they owned their little piece of the world. They were not going to be dead, real dead, for a long, long time.