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In "Stuck Together, Torn Apart", it showed Stewie jumping on his parents' bed. Brian told him to get down but he didn't so he jumped too high and hit his head, causing it to flatten to the "football" shape.
Although in 2 other episodes he was shown in utero & being born with his football shaped head.
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DevinRealistically because that's the way Seth MacFarlane decided to draw him but... In "Stuck Together, Torn Apart", it showed Stewie jumping on his parents' bed. Brian told him to get down but he didn't so he jumped too high and hit his head, causing it to flatten to the "football" shape.
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