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Mary Camden (7th Heaven)
In the world of 7th Heaven, every teenage misstep is a direct bridge to lifelong ruin and misery, and Mary's brief run-in with credit-card debt collectors is no exception. You mean I can buy things now, and pay later? she realizes with the kind of wide-eyed disbelief normally reserved for Amish teens on rumspringa. Though the Camden parents tend to overreact, you have hit bottom when you're covering your bills with coins from your baby brothers' piggy banks.
Jules (St. Elmo's Fire)
The '80s seemed like a time of wild financial abandon, when the money and hairspray flowed freely. But Jules should have known that borrowing money against her future paychecks was a bad idea that would lead to everything she owned being repossessed (except for the way-too-long curtains that were left to billow ominously as she had a total breakdown).
Rebecca Bloomwood (Confessions of a Shopaholic)
You might think the worst decision Rebecca makes is spending thousands of dollars she doesn't have on designer clothes, but really, it's getting a job at a print magazine in 2009. (And encasing her credit card in something that's as easily destructible as ice.)
Dewey Finn (School of Rock)
A successful financial plan should never rest on your ability to win Battle of the Bands, no matter how skilled your guitarist is.
Ben Stone (Knocked Up)
Actually, most of the men in Judd Apatow's movies aren't great with money (except the 40-year-old virgin — action figures were a solid investment), but Ben is a superstar of bad money management. He lives off a government settlement and doesn't even bother to check whether his get-rich-quick website idea already exists. Luckily, all his money woes can be handled in one "man-child grows up" montage.