Portland, Oregon, 1971. Bob Hughes is the charismatic leader of a peculiar quartet, formed by his wife, Dianne, and another couple, Rick and Nadine, who skillfully steal from drugstores and hospital medicine cabinets in order to appease their insatiable need for drugs. But neither fun nor luck last forever.

A boy named George Jung grows up in a struggling family in the 1950's. His mother nags at her husband as he is trying to make a living for the family. It is finally revealed that George's father cannot make a living and the family goes bankrupt. George does not want the same thing to happen to him, and his friend Tuna, in the 1960's, suggests that he deal marijuana. He is a big hit in California in the 1960's, yet he goes to jail, where he finds out about the wonders of cocaine. As a result, when released, he gets rich by bringing cocaine to America. However, he soon pays the price.

Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.

Raynor is an undercover narcotics cop. For his next assignment he chooses the more inexperienced but tough and good-looking Kristen. Their ultimate target is Gaines, a renowned but very elusive drug dealer. While doing their work they unexpectedly fall into a morase of drug-addiction and fall in love with each other. Despite subjecting themselves to the life of low class, one track junkies they do not get the evidence they want to convict Gaines, and instead are forced into using false evidence in court.

An amusement park mogul offers a random group of diverse people $1 million to spend the night in a decrepit former mental institution.

Bret Maverick is a gambler who would rather con someone than fight them, and needs an additional $3k in order to enter a winner-takes-all poker game beginning in a few days. He joins forces with a woman with a marvelous Southern accent, and the two try and enter the game.

After high school slacker Ferris Bueller successfully fakes an illness in order to skip school for the day, he goes on a series of adventures throughout Chicago with his girlfriend Sloane and best friend Cameron, all the while trying to outwit his wily school principal and fed-up sister.