When the snarky wisecracking villain loses something important to them and suddenly their arrogance turns into unbridled fury

Borderlands 2 - Handsome Jack when you kill his daughter

Kill la Kill - Nui Harime when her arms get sliced off (it doesn't hurt but she needs them for sewing)

Baldur's gate 3 - Auntie Ethel when you rescue the child she was using as a body shield

Crooked Kingdom - The main antagonist when instead of walking into his trap the heroes kidnap his pregnant wife