Gnome Golf, a sport that is practiced by using a Reckoning kill on a gnome, evokes this trope.
A really, reallydarkly funny moment in the Dead Kel DLC, when helping a Butt-Monkey gnome Pepin reach the goal of his quest. He races ahead of you, yelling about being vindicated and proving he's not a failure, when a spear trap goes off and jabs him in the head, killing him instantly and sending his corpse spiraling comically off a cliff. Even worse (and funnier) if you spot the trap first and just know what's coming.
From the Dead Kel DLC, everything Captain Brattigan says before embarking is hilarious. Most of the things she says after you arrive are also pretty funny. It's also strongly implied, if not outright stated, that several of the other shipwrecks on Gallows End are her fault. The worst sailor in Rathir, indeed.