
"They never let the rules get in the way of having fun."
After a brief flash-forward to Frank Sinatra as an old man, saying "I miss my guys," the movie's main narrative begins during high points in the solo careers of the Rat Pack: Dean Martin has become a big success despite the breakup of his partnership with Jerry Lewis; Sinatra's career is at its peak; Sammy Davis, Jr., is making a comeback after a near fatal car crash, and standup comic Joey Bishop is gaining exposure as an opening act for the other three. The Pack becomes complete when Sinatra reconciles with actor Peter Lawford, who has been ostracized since being seen out publicly with Sinatra's ex-wife, Ava Gardner.
Frank Sinatra

Dean Martin

Sammy Davis Jr.

Peter Lawford

John F. Kennedy

Bobby Kennedy

Joey Bishop

May Britt

Ava Gardner

Rocky Cooper

Joe Kennedy

Momo Giancana

Marilyn Monroe

Judy Campbell
George Jacobs

Joe DiMaggio

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Hank

Jimmy
Johnny
Jeanne Martin

Tom Dreesen
Reporter in Bar Fight

Mickey Cohen

Pat Lawford

Lewis Milestone

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Walter Winchell

Pit Boss
Broad at Casino

Frank's Secretary
Jefferson

Big John

Contractor

Rabbi
Frank's Assistant

Butler
Betty

Studio Head

Tourist

Bandleader
