Sam Giancana is a ruthless mob boss from Chicago. During a trip to Las Vegas, he sees a performance by the McGuire Sisters, a popular singing group with a pure image. Sam is attracted to Phyllis and begins aggressively courting her. The two enter into an epic romance, but it brings unwanted attention and tarnishes Phyllis's reputation. For Sam, however, the consequences are far more drastic, landing him in trouble with the law and his fellow mobsters.

The irreverent host of a political satire talk show decides to run for president and expose corruption in Washington. His stunt goes further than he expects when he actually wins the election, but a software engineer suspects that a computer glitch is responsible for his surprising victory.

Based on the life stories of the eccentric aunt and first cousin of Jackie Onassis raised as Park Avenue débutantes but who withdrew from New York society, taking shelter at their Long Island summer home, "Grey Gardens." As their wealth and contact with the outside world dwindled, so did their grasp on reality.