Jane (Whoopi Goldberg) is a singer in New York City, and she’s apparently been doing it for some time – but it looks like her luck has finally run out, because she’s got to find a new job, or at the very least a new place to do it. So she decides to head to Los Angeles to see if she’ll have any better luck there.

While she’s packing her things, her eyes settle on an advertisement that offers to pay someone to help drive to the West Coast. Answering the ad, she meets Robin (Mary-Louise Parker), who is headed West for her own reasons. On the way, they stop in Pittsburgh to pick up Holly (Drew Barrymore), who is an abusive relationship with her drug dealing boyfriend. That’s when things get interesting.

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Dan Foreman (Dennis Quaid) should be living the good life. He’s working as the head of ad sales for a major sports magazine and getting ready to coast into the best years of his life.

Unfortunately, the magazine has just become the part of a larger company in a corporate takeover, and he’s been “demoted” (which has to be better than being “downsized”) in the shakeup. To make matters worse, his new boss Carter Duryea (Topher Grace) is half his age and thinks he knows everything. He is about to find out that he doesn’t.

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