* [[KateModern Terrence]] is a brilliant character. He's basically a sociopath, but he gets enough {{Villain Episode}}s and StrangeBedfellows scenes that that doesn't matter, and he somehow manages to be both hilarious and terrifying, often simultaneously.
* [[WebVideo/DoctorHorriblesSingAlongBlog Dr. Horrible]], [[CatchPhrase P.H.D. in Horribleness]] and one of the most pathetic and lovable [[TheWoobie Woobies]] of all time while simultaneously being [[EvilIsSexy sexily evil]].
** Though Penny, surprisingly, is the one who gets the most backstory. Combine that with FeliciaDay's adorableness and, well, there's not much more to say, is there?
* Kaiba from ''WebVideo/YuGiOhTheAbridgedSeries'' for getting some of the best lines. [[ScrewTheRulesIHaveMoney Screw the rules, he has money!]]
** Hank Ishtar is win! He and Melvin!
*** Bakura and Marik too. Is it any wonder LittleKuriboh loves to use them so much?
** If abridged series characters qualify, then Sokka in ''AvatarTheAbridgedSeries'' deserves at least a mention. Twice the [[MetaGuy Meta]], twice the ButtMonkey, four times the funny ("So he's like... Kung Fu Action Jesus?").
** From ''WebVideo/SailorMoonAbridged'': Raye. She's an aggressive, shrill-voiced Satanist and pyromanic who just wants to sacrifice small animals in peace. Saddled with TheDitz as team leader, you can't help but feel bad for her when she meets her new team member, a ValleyGirl: OH MY GOD THERE'S TWO OF THEM!
** [[TeamFourStar Nappa and Vegeta]], the greatest comedy duo in the history of abridged series.
*** Goku from the same series. Whenever he's around, the episode is 10 times funnier.
* [[WebAnimation/HomestarRunner Strong Bad]]. He's quite possibly one of the most hilarious animated characters ''ever'', and I'm usually wary of cases where the AntiHero type becomes more popular than the plain, simple hero (usually leads to character bashing lobbed at said hero, etc). H* R makes it work because Strong Bad is actually funny and his instances of not being as cool as he says he is make him that much cooler. Plus, Homestar definitely works better as TheDitz than the heroic athlete so it all balances out.
* [[http://wondermark.com/jack-bulletproof/ Jack Bulletproof]], the Cop Who Plays by All the Rules. Because police procedures are there for a reason, and anyone who manages to be this awesome while doing the most reasonable and thought-out thing in any given situation deserves a mention.
* WebVideo/TheNostalgiaCritic: So messed up...and so entertaining to watch. Also, his singing voice. ''Dear God'', his singing voice.
** OH MY GOSH, [[WebVideo/BumReviews CHESTER A. BUM]] IS THE GREATEST CHARACTER I'VE EVER SEEN IN MY LIFE! He's deranged, stoned out of his mind, and absolutely hilarious.
* [[RedVsBlue Sarge]] is the epitome of DrillSergeantNasty, and it is amazing.
** And you gotta love Caboose!
-->'''Caboose''': Or, it happens to be a key all the time, and when you stick it in people, you unlock their death.
** Tucker. That is all. Bow-chika-bow-wow!
* EVERY SINGLE character from [[YogscastMinecraftSeries Shadow of Israphel!!!]]
* Carl Copenhagan from WebVideo/DemoReel. Sexy-accented MemeticBadass with a DarkAndTroubledPast and a hidden soft side. You were taken from the internet too soon, sir.
* I don't know whether she counts as a "character" or not, but SCP-811 from the SCPFoundation is one of the best written SCP items on the site by their own standards and EXACTLY how you should write a dangerous humanoid SCP item. She's got [[PoisonousPerson strange]] [[BreathWeapon abilities]] that, while [[CreepyAwesome cool]], don't come off as "super powers", she's dangerous without being malevolent, [[NonMaliciousMonster in fact she can be quite sweet]], and she even has a backstory that makes you [[TragicMonster feel bad for her]]. It's a shame she [[SugarWiki/NeedsMoreLove doesn't get as much attention]] as SCP-173, SCP-682 or even SCP-105.
** I like SCP-085 a lot. She's so nice!