Smug Snake/Web Comics

The Order of the Stick
- Daimyo Kubota is an always plotting, Genre Savvy aristocrat. Almost everything he does to try to usurp Hinjo's position is just plain hateful, culminating in him ordering the assassination of a pair of former commoners who were promoted to nobility. The wife is pregnant. When the plan fails, he murders his own number two with poison just to give himself time to escape. When he's captured, he plans to use his good publicity to avoid justice and humiliate Hinjo. Fortunately, right after he outlines the above plan, Vaarsuvius, not wanting any more distractions from the main plot, disintegrates him. His status as a Smug Snake is cemented by the fact that he just doesn't stack up against Big Bad and Complete Monster Xykon and his long-term planning henchman Redcloak. He's also horribly naive, and thinks taking the city back from Xykon will be a trivial matter.
- Likewise, Nale, leader of the Linear Guild and Elan's Evil Twin, isn't nearly the Magnificent Bastard and evil mastermind he likes to think he is; Vaarsuvius points out that most of his plans, which he likes to think of as works of genius, are in fact rather trite and cliched (if nevertheless somewhat effective), and he has the tendency to come off as being rather smug rather than magnificent. Elan and Nale's father, General Tarquin, a genuine Magnificent Bastard, more or less confirms this when he is insulted by being compared to Nale:

"Your brother was a disorganized buffoon who cared more about satisfying his own ego than any realistic plan for world domination. All he ever cared about was that everyone knew HE was the victor, even when the situation called for keeping a low profile."

- Tsukiko is an incredibly vain sorceress who believes she's the heroine of some Twilight-esque novel with Xykon as the dashing undead love interest. Worst, she actually believes she can treat Redcloak like dirt and constantly get away with it, up to the point of replacing him as Xykon's Dragon. Redcloak ultimately demonstrates that she's very, very mistaken on every count, and way over her head.
- Bozzok qualifies to a certain degree. He just cannot let his beef with Haley go and goes as far as to turn his main enforcer Crystal into a self-aware flesh golem to finish the job while he gloats, not thinking for a second about how it could backfire. And it did. Grubwiggler's farewell quote sums it up nicely.

"Farewell, Bozzok. You were never as clever as you thought you were."

The slimy, manipulative businessman Serk Brakkis in Dominic Deegan: Oracle For Hire is a walking embodiment of this trope. He uses his power to utterly ruin people's lives, takes their money and then hides behind Byzantine laws. In the end, however, he is trampled under a very satisfying Humiliation Conga, beginning with a fencer flicking his wig off ("Toupee!"). Much later, when it looks like he's going to beat the rap after another foiled scheme, Celesto shows up and turns him inside out.
Faz in Shortpacked is a toadying, nakedly ambitious sycophant with a permanent smug expression and a tendency to openly plot against and undermine the people he works with. Absolutely no one in the store, including his boss, particularly gives a damn about his continuing existence or welfare.

Faz: Your thoracic diaphragm heaving in anger is not unlike how I picture your anatomy during our inevitable lovemaking.

- If you need even more evidence of his Smug Snake status, just read his entry on the cast page: "Shortpacked!'s most annoying recruit has an infuriatingly smug grin you'd love to remove with a grenade launcher."
  - It doesn't help that he also comes off as a slimier Casanova Wannabe when trying to convince Amber to sleep with him, including pulling out the Kinsey Graph when Amber said she was a lesbian (Long story)
    - He's obliviousness over the fact that Amber was really his half-sister isn't helping his case either.
Vriska Serket of Homestuck. She's a spiteful, conniving, BLUH BLUH HUGE BITCH with a serious case of Chronic Backstabbing Disorder. She also would like to think that she's the best Troll, but really isn't capable of manipulating anyone without resorting to Mind Control, and usually ends up being manipulated herself by other characters' Batman Gambits.
- Oddly enough, she may actually know this; her Munchkin-ry and Glory Hounding are implied to be an attempt to match her warped idea of what will make people respect her, and part of her falling-out with Terezi was due to jealousy that Terezi could do more with no special abilities than Vriska could with Psychic Powers.
Sluggy Freelance: Ralfoy Malfoy, an obvious parody of Draco Malfoy. He takes the smug-snakeness to the extreme by acting smug, even though his "enemy" is the adult but childish Torg who will inevitably just do something like give him a wedgie (or even tell him to do it himself) and send him scuttling away. Only in the 3rd parody did he actually manage to rise to the status of a real adversary for a while... and that was at the expense of getting a video put up on YouTube of him saying he thought a ferret was sexy-cute.
Umbria/Zaedalkaah from Our Little Adventure. She believes herself to be a skilled liar and cunning calculator, but most of what was actually going in her favor is simply luck. She used to be an extremely powerful demon, but has been reborn into something considerably less powerful. It doesn't make her act any less entitled however...
Shiplord Scrabben in Schlock Mercenary is a tactical genius wannabe who hilariously overestimates his chances against Karl Tagon's squad - proudly commanding a repurposed freighter he calls a warship and mistaking the Breath Weapon warship for a freighter, among other things. The narrator incessantly makes it clear how out of his depth Scrabben is, and he's lucky that Tagon wanted him and his whole crew alive after the humiliating defeat he suffers.