Its story follows a young shoe designer, Drew Baylor, who is fired from his job after costing his company an industry record of nearly one billion dollars.

Deciding to postpone his suicide and bring their father's body back to Oregon, he then becomes involved in an unexpected romance with Claire Colburn, whom he meets near the start of his journey.

When his latest shoe, meant to be his great life accomplishment, is found to have a flaw, it costs the company $972 million, and Drew is shamed by his boss, Phil, before he is asked to speak to the press—his future unknown and likely finished at Mercury.

Disappointed in his failure, and the subsequent breakup with his fair-weather office girlfriend, Ellen, Drew stacks his expensive clothes and other valuables on the street for scavengers to take, then prepares to commit suicide.

He stops at the last moment to answer a persistent phone caller, who turns out to be his sister, Heather, telling him that his father, Mitch, has died while visiting family in Elizabethtown, Kentucky.

Depressed about his work failure, he tries to ignore the bubbly, quirky Claire who has nothing to do on the flight except talk to him incessantly about Kentucky and alludes to her boyfriend, "Ben", who is a workaholic.

While staying at a hotel, where a raucous bachelor party and wedding reception is being held, Drew calls his mother and sister, then his ex, Ellen, as he struggles with boredom and depression.

Drew follows Claire's map home, spreading his father's ashes at memorable destinations along the way until he reaches the "World's Second Largest Farmer's Market" in Nebraska.

There, a series of notes and clues gives him a choice: to either follow the map home or to go in a new direction, searching for the "girl in the red hat."

[citation needed] Ashton Kutcher, Seann William Scott, Colin Hanks, Chris Evans, and James Franco all auditioned for Orlando Bloom's part.

[citation needed] Recognizable settings for scenes shot in Louisville, Kentucky, include the Brown Hotel, Highland Middle School, and Cave Hill Cemetery.

[3] Roger Ebert published a letter from reader Todd Zimmerman which makes the observation that the film is really a hidden story of an angel who has fallen from grace.

Claire, the angel, is met in the heavens (the empty plane) and has decided to guide Drew through his depression, suicidal thoughts and redeem himself from failure.

The website's consensus reads: "This story of a floundering shoe designer who returns home for a family tragedy gets lost in undeveloped plot lines and lackluster performances.

Club created the term "Manic Pixie Dream Girl" to describe the "bubbly, shallow cinematic creature" stock character type that he stated Dunst plays in the film.