The "Battle for Barthis" arc of Dominic Deegan: Oracle For Hire concludes with Dominic telling Serk Brakkis, in exacting detail, how Brakkis's life is about to be ruined. Brakkis then loses his toupee, soils himself when Luna shows him a terrifying illusion, and for the grand finale, gets teleported off to stand trial for his crimes... by the lightning mage known as the Maestro. And given the look on the Maestro's face, it will not be a fun trip.
Doubly subverted when Brakkis is on the verge of manipulating the law into giving him a "Get out of Jail Free" Card when Celesto Morgan brutally murders him.
Tales of the Questor has the "Wild Hunt" arc, where the Unseelie Princeling leads the Wild Hunt after Quentyn. Turns out, that's the last thing he should have done: not only are the Racoonan as a whole gifted with the boon of being forbidden fruit for the Hunt (to the point where the Hunt isn't allowed even in areas where there's Raccoonan living), but Quentyn himself is an extra-special case - he's one of the White Stag's Marked, which means that the princeling has broken two of his race's most important laws. Either of the two alone would make the whole thing an illegal Hunt, but the two together combine to make things far worse for him. Since Quentyn not only won the Hunt - the Rooster did crow, after all - but the Hunt itself was illegal to begin with, the price the princeling has to pay is tripled. Quentyn uses his three boons to first set free every single debtor and bond-slave in the lord's service (which amounts to everyone in his service) and nullify every debt or favour owed to the princeling (leaving him a pauper, since the Sidhe economy works on favours owed). Then he makes the princeling return "everything garnered unlawfully" - Quentyn was aiming for just the children the Unseelie stole, but he gets the duke a ridiculous amount of treasure (although the Genre Savvy duke mentions that he'd be happier without it - that much wealth will only cause trouble sooner or later, after all). His third wish is translated on the forum thus: "Dolan, princeling of the Unseelighe fey...wicked enemy of mortal men...depart now, you and all your house beneath you, harming none...never to hunt this plane again." The result is that the princeling suffers a Villainous Breakdown, literally rending his garments and cursing Quentyn's name, and vowing to wait as long as it takes for him to be legally allowed to seek his revenge on Quentyn (and his children's children's children).
The Big Bad from The Order of the Stick, Xykon, seems to be particularly fond of this trope (though he usually kills his victims in the process anyways). He seems to have a thing for humiliating the paladin O-Chul in particular, starting here.
However, in O-Chul's and Vaarsuvius' case, not only did they not break, but also Xykon and Redcloak were the ones on the receiving end.
In Drowtales this is Syphile's very existence in nearly every appearance she makes in the comic. Right up until her death, at least she's out of her misery.
After the timeskip the Sharen clan, in particular Sarv'swati, wind up going through this as they increasingly start losing the war against the upstart Sarghress clan. First half of Sarv'swati's army takes off with her little sister Zala'ess so Zala can make a power play and earn the loyalty of a neighboring city, then the Body Double of her mother (who Sarv'swati helped kill) she's been using to keep her hold on the city is publicly assassinated and one of the few clans in the city still helping her pulls back their troops in response. Then her pet project of a Penal Colony first has most of the slaves freed by a Sarghress squad and later falls completely when the rest of the Sarghress army arrives and demolishes what was left of her forces there before using the tunnel leading from it to sneak attack her main fortress from behind, with some of her other sister Nishi'kanta's family sabotaging their defenses from the inside before fleeing as payback for Sarv's own betrayal years before. The icing on the cake comes when she's forced to make a Last Stand at her mother's tower, nearly gets killed by her own great-niece, gets a "The Reason You Suck" Speech from her Old Retainer about how the entire situation is her own doing and fails to kill him for it since she unknowingly dropped her axe in her tiredness, and then breaks down like a child in front of her mother's collapsed throne room begging her to come back. Her final attempt to win back her honor with a rematch with Quain'tana also fails miserably when her little sister Zala'ess secretly sabotages the match by trapping Sarv's foot with some magic, ending with Quain'tana delivering the killing blow to Sarv's head.
The Demons of the Dimension of Pain in Sluggy Freelance probably get the longest one ever. first there were their series on embarassing failures at trying to kill Torg on each Halloween, Lord Horribus' was the worst between his unexpected diahrrea and getting controlled by a magic spell through complete accident. Horribus is then exiled into being a camreaman to a demonic Steve Irwin parody. The other dimension of Pain demons go through a goofy election period that ends with Terribus selling his soul to a mortal, who actually turned out to be an angel who gradually transforms the Dimension of Pain and its residents into some tastes like diabetes Carebears meets Barney land. After finally beating the angel, they all get trapped in balls and get stuck in a chasm. They get out of their balls through an innuendo ladden process that leaves them with high pitched voices and no will to do anything. Then Terribus in disguised as the Demon King makes them start a church and play Bingo games for crappy prizes. After throwing out Terribus they then attack the real Demon King who then makes them go through excercise/excorcise routines.....really, after all that, is it any wonder they go bezerk all over the Dimension of Lame?