A PR specialist refuses to market a car called a "Howard" - a colossal error that loses him a billion and makes him a national joke. He loses his hair, shaves his beard, takes a new name, and moves to Martha's Vineyard. Jump ten years: "Rolly" is a popular local whose sangfroid evaporates when the Howard's inventor moves to the island. Rolly, his old self unrecognizable, hatches a plan to rid the island of his nemesis; he also decides to woo the billionaire's wife. Fellatio, a former girlfriend, a woman who's lost weight, her boyfriend, the band Chicago, a menacing Chechen, a bus load of ill children, and a pair of ne'er-do-wells with experience with explosives figure in the story.

In 1987, James Brennan's dreams of a summer European tour before studying at an Ivy League school in New York City are ruined after his parents have a severe career setback. As a result, James must get a summer job to cover his upcoming expenses at the decrepit local amusement park, Adventureland, where he falls in love with a witty co-worker, Emily Lewin. In that bizarrely shady workplace, the young carnies have unforgettable and painful learning experiences about life, love and trust while James discovers what he truly values.

The fortunes of a husband and wife differ drastically after they divorce.