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Stewie loans Brian money to pay for his worm medicine in 'Model Misbehavior' and Brian reluctantly agrees to work for him.
Stewie is a bookie in 'Patriot Games' that beats up Brian when he is slow to pay off a bet.
Stewie also loans Brian money to pay his rent to live with Jullien and then moves in with them in 'Movin' Out (Brian's Song)'