- Drizz'l in 8-Bit Theater. First, he was humiliated when the "true guardian" he bought turned out to be a platypus. Then, he went without a sword for a good majority of the comic and teamed up with the most incompetent antagonists possible. After he finally assumed leadership of the Dark Warriors, his first plan to quit their royal accounting job was an utter embarrassment. Then he was voted off the team (right after finally becoming leader and running a huge, evil castle) and forced to Heel–Face Turn (sorta) and ended up hating the Light Warriors even more. Then the final showdown he was waiting for was interrupted by a pointless election. Then his plan to kill everyone else backfired. Then the Fiends who mistook him as the one who summoned them from Hell were unable to kill his teammates because of family ties. Then said Fiends were suddenly killed off (again). Then his plan to take over the world using the four elemental orbs of light came to a quick end when Sarda pointed out that they have no idea how to do that. Then said nigh-omnipotent jackass wizard who did it subsequently mind raped the whole team and forced them to run away. And finally, he is the only Very Real Light Warrior unhappy about being credited with saving the world, probably because he never got to be an actual villain and/or due to the whole stupidity of the situation.
- About half the Card Carrying Villains in Antihero for Hire fit this trope.
- Kumimi of APT Comic, considering how hard she's working towards that "invade the planet" thing.
- Well she IS a Sgt. Frog character.
- Waldo and Steve in the webcomic College Roomies from Hell!!!, though they are far too ugly both physically and socially to ever be truly sympathetic.
- Zenith from Commander Kitty zigzags this to hell and back...especially the sympathetic part, considering what happens. Her ridiculously petty motivations/desires and long-winded ranting speeches certainly come across as this, as does her failure. Later, though, we do see she is capable of some pretty horrifying stuff; yet she's also capable of being adorably helpful when in "good" mode. That just makes her subsequent reversion, painful shutdowns, and nearly And I Must Scream status later on just painful to watch....and then she goes completely off the deep end and got more powerful for it, basically becoming SHODAN.
- In El Goonish Shive, technically, Magus was apparently behind the v-five Elliot incident, and tried to manipulate Ellen within some plot that sounds quite dubious. And is not very good at this. But he's in desperate straits, which isn't even his own fault (unlike Abraham's case). And he's still reluctant to kill a guy who stands in his way even when pushed hard to do it.
- Dr. Kinesis in Evil Plan. His technology gets stolen, the other villains laugh at him, and on his minions' first mission, they bump into a brand new superhero.
- Clubs Deuce from the Midnight Crew Interlude of Homestuck; the rest of the Midnight Crew are pretty big bumblers too (aside from Diamonds Droog) but can go under Faux Affably Evil, depending on your personal Alternate Character Interpretation. Also amusingly subverted with Clubs, as Ditziness aside, he has the highest body count of the Midnight Crew. Mostly by accident.
- In Act 5 of Homestuck, Eridan is a genocidal snob who aspires to kill off all the lower-class, land-dwelling trolls. But none of his schemes ever work, no one takes him seriously, and the narration itself describes him as an Ineffectual Sympathetic Villain:[Y]our penchant for mass murder notwithstanding, people tend to regard you as a BIT OF A TOOL.
- It's later revealed that he really doesn't care about killing people, he's just doing it to stay close to his hatecrush. He also very easily could have triggered mass-genocide if he wanted to, but actually works to keep it from happening because Feferi would be upset otherwise.
- Eridan becomes a full-on subversion when he loses both the "sympathetic" and "ineffectual" parts in Act 5 Act 2. The crush mentioned in the above line? He kills her as he leaps across the Moral Event Horizon.
- Though he switches right back to ineffectual when Kanaya comes back from the grave as a vampire and effortlessly fells him. Like a tree.
- Jack Noir starts as this. Later into the story...he's significantly less ineffectual or sympathetic.
- Likewise Caliborn comes off as too much of a Stupid Evil brat to be a true threat. And than we see how he ended changing his name to Lord English...
- In Act 5 of Homestuck, Eridan is a genocidal snob who aspires to kill off all the lower-class, land-dwelling trolls. But none of his schemes ever work, no one takes him seriously, and the narration itself describes him as an Ineffectual Sympathetic Villain:
- Fructose Riboflavin in The Inexplicable Adventures of Bob!, who has been trying and trying and failing to take over the Nemesite Empire for so danged long that you have to pity him, just a little.
- Cassiel from Misfile desperately wants to be Rumisiel's nemesis and is constantly plotting his downfall. Too bad she makes the Team Rocket trio look competent and effective.
- Jokerella from The Non-Adventures of Wonderella is... Kind of a mess of self-esteem issues who isn't really very good at being a supervillain.
- The Minion Master from Sluggy Freelance.
- In an alternative universe, he's Not So Harmless.
- The Flaming Prince from Van Von Hunter.
Ineffectual Sympathetic Villain / Web Comics