Everybody Loves Raymond
Win, Lose, or Draw
S1 E9:
Ray gets tired of being treated like a kid at his father's poker game, so he ignores his father's advice and ends up losing all his money. Debra wants Ray to act like a mature adult and ask Frank for his money back, but Ray is too stubborn.
Starring
Sawyer Sweeten, Sullivan Sweeten, Joseph V. Perry