Doug's in Debt!

For a class project, Judy lets Doug borrow one of her theatrical Napolean hats after making him sign a contract. Doug loses the hat and Roger finds it and won't give it back to Doug. In order to get the hat back from Roger, he asks Doug to do many favors including stealing a plastic cow. After all the favors are done, Roger still refuses to give the hat back. Since Doug can't return the hat to Judy, he must suffer the consequences.

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S05E07 - Doug's Big Comeback