Dungeon Keeper Ami features an awesome version of this over an entire story arc. The War on Death Arc, to be specific. First the Dark GodCrowned Death steals the Avatar's Mantle from Empress Mercury, takeing the time to taunt her in the process. That was a great idea. Really. What happens is this: First, Mercury personally assassinates the Death Priest responsible. Then, once Crowned Death attempts to use the Mantle in his bloody ritual, Mercury's forces successfully attack the temple in question half a world away, with only three days warning. Not only does Mercury's Airship Fleet completely trounce Crowned Death's forces gaurding the temple — she consumes one of his lesser aspects, and rescues the hostage sacrifices. All eight thousand of them. Soon after Mercury uncovers the existance of a massive swimming fortress-temple, Crowned Death's base of operations. Soon the temple is destroyed in a tremendous conflagaration of Chlorine Trifloride. Outraged, Crowned Death attempts to kill Mercury useing corruption to rot away her dungeron, only for Mercury to escape him... and Azaratha, the Mighty Tyrant... AND The Unraveller of Mysteries. Three Dark Gods working together. In desperation, Crowned Death turns to Mukrezar, a powerful keeper he revived using the Avatar's mantle, only for Mukrezar to slaughter the leadership of Crowned Death's cult.
Jeft in With Strings Attached: First, the Hunter ends up befriending the four rather than fighting them. Then the five of them destroy one of Jeft's pet places of evil, the Plains of Death and its associated Heart of Evil (which is very expensive). Then he sees some of his best and toughest baddies easily and quickly neutralized with no danger to anyone. Then the Hunter manages to throw his mind-controlling BFS over a cliff and escape Jeft's clutches entirely. Finally, Shag and Varx inform him that they've ratted on him to the Dalns gods, prompting an Oh Crap! moment and his quick exit from the book.
Very blatantly done to Sasuke in "Connecting the Dots", the Naruto/Justice League Crossover. Having just lost an eye in battle with Naruto, Sasuke is taken by the Spectre to Gotham City, where :his chakra is taken away and he is beaten to a pulp by Johnny Rancid and his gangs, until he's forced to beg. Spectre very brazenly says that he does this to teach him humility.
Marceline in Adventure Time fanfic, Alex. Most notable in chapter 4 where she gets owned by her own spit, beaten to a pulp by Alex, gets thrown with rotten tomatoes, and attacked by Finn and some wolves.
Suddenly, a water balloon splashed into Hobbes' head. "ACK!" Hobbes yelled. It was then that Hobbes realized that Socrates hads pushed Hobbes over sending him tumbling down the hill. He landed in the creek. However this wasn't enough for Socrates. Socrates rolled the garbage barrel over to the hill, and dumped it. Over a ton of garbage colapsed onto Hobbes, just as he was climbing out of the creek. Then, Socrates grabbed a barrel full of mustard, and sent it tumbling down the hill, screaming in anger. It hit Hobbes, and he went tumbling back into the creek, now covered in mustard.
Rainbow Dash ends up going through this in Ditzy Don't after Ditzy is turned into Mademoiselle Doo: she's so badly outclassed that she and Ditzy basically switch roles, leading to her public humiliation and being fired from her weather management job, followed by Mademoiselle Doo deciding to start babying her. And that's before she goes obsessive and starts hunting Dash all over town until she's snapped back to normal. All of this helps lead to Dash's Jerkass Realization.
Atlas Strongest Tournament: Rarity puts Blueblood through one of these during their match in the preliminary rounds, as payback for the Gala — first, she hits him in the eye, then in the pole, then immobilizes him with acupuncture needles (which also cause him to lose control of his bladder) before finishing him off.
After Valmont's attempted coup, he gets beat up by Tohru, before Jade has her Shadowkhan strip him and dump him in public, where he ends up getting arrested. And this is after the months of living like a common thief before Jade recruited him.
Daolon Wong fails to restore his power, gets beat up by Jade's Shadowkhan, locked in a closet, sent back to prison, tricked into helping his enemies, sent back to prison again, and then dies of old age. You almost feel sorry for the old bastard.
Drago's attempt to steal the Talismans is thwarted by Karasu, his bank robbery attempt is interrupted by Blankman, to whom he loses the subsequent fight, Karasu prevents him from stealing the immortality power from Scruffy, and he gets sent back to the future, where the Matriarch (future Jade) has him beaten with metal baseball bats.
Earth and Sky: After Chrysalis' impersonation of Diamond Tiara is exposed and she's arrested, Blueblood looks like he's in the clear... only for Fancypants to end up forcing him to hand over majority shareholding in his own company at risk of his involvement being uncovered, followed by Diamond Tiara's lawyers blocking his access to her money. And then on top of that, his airship gets blown up by the Wrong Brothers' errant rockets.
And things just get worse for him in the final chapter, as Diamond returns, divorces him, and leaves him with so little that he'll have to move back in with his mother (an apparent Fate Worse Than Death).
Hivefled: the extremely Not Safe for Work depiction of Dualscar's death is one of these. He's offered his freedom in exchange for telling a joke, attacks the Grand Highblood instead, and ends up with his own gun lodged in an uncomfortable place, in front of his entire crew and the Empress (who, incidentally, he intends to beg for help until he realises she's masturbating), while still being forced to tell the joke. Which he doesn't even manage to finish.
Lightning Dust in the Reading Rainbowverse. Let's see. Lightning was kicked out of the Wonderbolts, which ruined her relationship with her mother, set up on a blind date with the mare that she blames for that, accused of getting said mare into prison and getting more dissapointment from her mother, went into heat for the first time and became heatlocked on said mare, attracted the attention of an anonymous eldritch abomination, had a mail organ drawn on her forehead by said eldritch abomination, hospitalized herself trying to do a sonic rainboom, was disowned by her mother shortly thereafter, and forced to wear a frilly dress.
The Conversion Bureau: Conquer the Stars gives a truly brutal one to the ponies who supported Conversion, which is so thorough that it almost Crosses the Line Twice. Let's see — After the Gryphon Queen declared Celestia's Omniscient Morality License was revoked at the end of Not Alone, Equestria goes through this. First, all of the other countries in Equis launch a massive economic embargo on Equestria, forcing the heavily import-dependent country to develop on its own, while dealing with scarcities of several different resources in the meantime. Some time later, negotiations were re-established for the next five years, during which things seemed like they'd be okay... only for, on the fifth Hearth's Warming Eve, all nations to declare war on Equestria simultaneously. The following campaign was so devastating to Equestrianote even Celestia herself plus an entire armada of her best royal guards were crushed by Gryphon's fleet in front of the entire populace of Manehattan that the Princesses were forced to relocate to another planet (see Death World above), and even that was done by leaving several pieces of Equestria, like the entirety of Appleloosa and literally half of Hoofington, behind. By the time the USS Calvin discovers Equestria, the country is ravaged by civil war, extremely impoverished, has lost use of the Elements of Harmony, and a resistance movement is midway through a plan to "bring the Princess to her miserable knees". You almost have to feel sorry for them... almost.
In the The North Remembers, House Frey, who are already despised by many for their role in the Red Wedding, are betrayed by the Lannisters when they force Walder to send his daughter Roslin to Casterly Rock as a hostage. Then as punishment for letting Jeyne Westerling escape from Riverrun, Cersei orders Roslin and the Westerling family's execution, effectively nullifying everything House Frey gained from the Red Wedding. Walder, who at that point was already suffering from apoplexy, dies upon hearing the news. And if that wasn't enough, his successor Edwyn takes two dozen of his relatives out to seek revenge against the Lannisters... only to be ambushed and hanged by the Brotherhood without Banners.
Cori Falls makes it a point to give Ash Ketchum one of these in every story after a certain point in her timeline, including but not limited: having James's baby Articuno peck and curse at him in Pokemon language and being given a wedgie while everyone makes fun of his choice in underwear, being called out on every single mistake he's ever committed, Brock and Misty turning against him and siding with Jessie and James, losing every battle or other competition he participates in, and more than half his Kanto League badges revoked. By the end, he's little more than a pathetic Man Child who exists to be mocked and feared as a dirty, smelly monster.
Tobias from Pokemon gets one in a fanfic that doubles as a Take That, Scrappy!. Gets stripped of his title? Check! Has his Legendary Pokemon confiscated? Check! Goes to jail after it's figured out that they're not Legendaires but genetically altered Pokemon, which is illegal? Check!
Tellygunge's fictional 2011 revival of Noel's House Party (plus the sequel/Dead FicDavina's House Party) uses this with a lot of gunge. Interestingly, the fic used a voting system on who would go through one. Although some are subverted due to the victims enjoying it. Cheryl Cole, Sheridan Smith, Zoe Salmon, Amanda Lamb, the Coronation Street girls, Miley Cyrus, and Rhianna are all subjected to this in the 2011 revival, while Sarah Michelle Geller, Bérénice Marlohe, the Strictly Come Dancing contestants, Sophie Dahl, Oliva Godfrey, Hayley McQueen, Claire Tomlinson, and Sally Bercow undergo this in Davina's House Party. Rachel Riley also takes the brunt of it in every episode after announcing the half-time results in Davina's.
Happens to Bobby in thisLoud House fic. First he's dumped by his girlfriend, Lori for having small genatilia, then his reputation at school ends up being ruined for it, as Lori sends a picture of his small penis to her friends and then becomes a laughingstock. When he manages to catch a date with Leni, she informs him that Lincoln is more well-endowed than him, complete with a nude photo of him to prove it, further embittering him. Things start to move South even more when she starts to feel discomforted by making out with him, to the point where she kicks him in the groin and runs away for help. A man, coming to Leni's aid then drags him out of the car and pins him down to the ground, furtherly injuring his groin and causing him to cry. As a result of the incident he's tried as an adult for attempted rape and sentenced to two years in the county jail. Once doing the time, he's ridiculed by other prisoners for his small penis size in the shower and just guess what happens after that.
Minimoose in Episode 4, as he gets dragged across the city by GIR and Phil as the latter chases MIMI, repeatedly getting slammed into things in the process, and finally gets tossed into a meat processor.
Viera puts Gaz through this in Episode 8 in an attempt at teaching her humility, first through a bad luck curse, and then magically dressing her up as a clown in front of the whole skool.