Becoming the Mask: After spending ages actively averting it, when he's had enough of everything he rants about all the crap that's happened to Link. Although, ranting about his life as the Critic would probably take up an episode of its own.
Also done at the end in a sadder way with Ma-Ti, he throws away his tie when he's rushing over and Ma-Ti knocks his glasses off. Those were the last two "Critic" identifiers left.
Break the Haughty: Done nicer than in Kickassia (he does get to be a good guy instead of just being willing to commit murder-suicide) but he still gets punished for being greedy. And with his reaction to Ma-Ti's death, it overlaps with Break the Cutie.
Character Development: From being a greedy asshole to a capable leader who can boost morale with a Rousing Speech. Not only that, but he keeps himself relatively stable compared to how he was in Kickassia. At the end, he even considers going on another quest to resurrect Ma-Ti. He also seems to have gotten his greed under control as he decides to hide the Gauntlet rather than profit from it after seeing the magic it uses is real.
The development also seeps into his usual episodes, in both a good and bad way. Good news is that he's learned all actions have consequences and pain is necessary, bad news is that his Miles to Go Before I Sleep side has gotten worse.
Hypocritical Humor: The Critic complains bitterly about the frequent spelling errors in the map. Note that Doug has, in the past, spelt "Nostalgia Critic" incorrectly in his reviews and manages to mess up the spelling in the credits of Suburban Knights.
Innocent Fanservice Boy: Until it was pointed out to him, he had no idea that he was wearing such a... revealing costume.
Reluctant Fanservice Boy: According to Iron Liz, Doug requested strongly on the first day that nobody look up his skirt. But due to wind and an apparently ungainly falling over, everyone did.
Jerk with a Heart of Gold: Film Brain, Ma-Ti and (to a lesser extent) 8-Bit Mickey get treated badly, but he listens to his team, sulkingly accepts the "lady lessons" Lupa teaches him and worries about the others when he realizes that the Big Bad is tracking them. He's also VERY upset about the death of his comrade.
Betty and Veronica: It's in the background, but she's (intentionally done, Lindsay said in the commentary) Ship Teased with Critic, Benzaie and Jew Wario. As we know, Critic's the femme, bratty, fucked up ball of need, while Jew Wario and Benzaie both prove to be men she can cling to and offer silent support. But in the end, those two seem to have lost.
Bilingual Bonus: In part one, the Chick says a line in gaelic- "pog ma thoin" (kiss my ass) which is translated as "it's cool".
Dull Surprise: It's especially obvious during the scenes in Doug's house and the elf montage sections (though the former was justified by Lindsay, as she felt the Chick would not care about the whole "being duped again" and be bored).
In the elf scenes, it's worth noting that the character she's playing was also noted for this, so it could be intentional.
The Stoic: Most of the time she's not really bothered by anything.
Not So Stoic: She's visibly distressed by the idea of Malachite getting his gauntlet back ("From the sound of it, everyone's gonna be screwed if he gets a hold of it!"), and is clinging to Jew Wario and teary-eyed during Ma-Ti's funeral.
Badass Beard: Though he runs out of Sharpie after his first appearance.
In the commentary, Doug intended for Linkara's make-up pen beard to last for the entire movie. Linkara was against it, due to both Harris' beard not being black in the movie, and the fact that he would have black smudges on his face on the crossover videos.
The Cast Show Off: Once again demonstrates his rather nice singing voice, but he keeps getting interrupted by the others in his group. He finally gets to sing a complete number at the end of Part 7.
Chekhov's Gunman: His persistence of a song inadvertantly leads to the Critic learning about the Necronomicon at the end.
Chest Insignia: The costume bears the Atop the Fourth Wall hat-brick-fire logo.
Combat Pragmatist: After fighting the Guardians for a while with his sword, he exclaims "Screw this!" and pulls out his gun.
Unexpected Character: Much like Tom, his costume was up for debate and being King Arthur from a musical was never considered. However, this could also be considered a Call Back to his review of Power Rangers Zeo #1, wherein he states that Camelot is his "favorite movie & musical EVER!"
Ax-Crazy: Believes his figurines are alive. 8-bit Mickey thinks he's a little too into character.
In Part 2 Mickey questions his belief that his "friends" are real... to which Phelous replies, "They're more real than you are!"
In Part 3 he talks to his "little friends" about killing Bennett... in front of Bennett.
Becoming the Mask: To a far greater extent than the others. He truly believes that he's the Rockbiter and that his action figures are alive.
Subverted in Part 6; he's just really good at staying in character.
Character Development: From Kickassia. He went from gleefully strangling the Critic and telling the others to "have fun" as return for all the idea-stealing, to coming out of a funk to protect him and calls him a friend.
Companion Cube: He starts treating a pair of action figures as being alive as soon as he puts on the costume.
Stealth Pun: Unintentional — he was supposed to say "Crom" when he makes his entrance, but Benzaie said "Come". This fits however with Nostalgia Critic's review of the Conan movies, where he includes a clip of Arnold comparing working out to "cumming".
Panthera Awesome: While his costume is somewhat lackluster compared to the others', he is able to get in a few punches during the fight scenes and can make a very epic roar.
According to Iron Liz on Linkara's commentary, the tail (which eventually fell off because Bennett stepped on it) was even worse, since it's positioning at the bottom of the suit rather than at the tailbone made it look like a penis.
Running Gag: "I'm Willow." (in a video, he even lampshades saying "Basically my only line in this is 'I'm Willow'")
Unexpected Character: In-universe and out. No fan even knew who he was, and the team didn't realize who he was until he told them. Mainly because Willow is played by a little person while Tom is incredibly tall.
Red Herring: An unintentional one, but because the illustration of the gauntlet's origin had Aeon wearing a pink ring, viewers thought that it was Spoony's. According to Spoony this was completely unintentional and he wishes he hadn't worn the ring because of this.
Nice Guy: Even though he does have some fun acting flirty and just a touch raunchy as Jareth, it's still Jew Wario. In the special he really goes out of his way in giving Malachite more kindness than he deserves.
Non-Action Guy: Despite his lack of direct attacks, he makes for one hell of a "debuffer".
Nostalgia Critic: We'd like to thank Todd for handling the cremation, even though I don't think any of us want to know how, or why he did it.
Todd: *holding a lighter* Yeah, it's probably best you don't ask.
Recognition Failure: At first, he thinks the cast didn't know who he was dressed as (even though they have an Inigo Montoya). Then he notices that they aren't recognizing Todd. Presumably the hoodie was his sole identifying mark to them.
Translator Buddy: Translates Spoony's high-flown fantasy dialogue into mundane terms for the rest of the group.
Vitriolic Best Buds: Apparently with the entire cast. When the Cloaks attack, he tells them to stop because:
Todd: I barely know these guys, I just do music reviews! I don't even like these people!
Curb-Stomp Battle: Does this to both Jaffers and his group and the TGWTG crew. Of course, they're a bunch of geeks with barely a real weapon between them and he's an immortal Magic Knight.
Establishing Character Moment: He is walking in an open field and tries to hitch-hike. He is picked up by a very flighty, materialistic guy, which prompts him to complain about the effects of this century's modern technology on humanity, and eventually kills him with supernatural powers.
Evil Luddite: Given his backstory, it's no wonder he loathes all technology.
Evil Mentor: Malachite taught Jaffers magic when he tried to trick Jaffers into finding the gauntlet for him.
Hidden Agenda Villain: For most of the story it's hard to tell just what his deal is, killing two people for relying on technology and walking around with an evil Leitmotif, but then helping Group 2 by returning their map. Turns out that Malachite couldn't find the gauntlet on his own, so he used the Channel Awesome crew to find it for him, sending the map as a chain letter and putting a tracking spell on it.
Omnicidal Maniac: It's implied a few times that he may not be as hypocritical as Team TGWTG think he is and may have just been after the destruction of the world out of revenge for not being the founder of modern civilisation.
Spell My Name with an "S": The special shows his name as both Malecite in the actor credit and Malachite elsewhere. Given Doug's propensity for misspelling words, it is unknown at this point which is the correct spelling (though probably "Malachite", which is an actual word and makes it a Meaningful Name.
The Unsmile: After he's banished to the All-Around Cafe he's forced to smile for the customers, but is only capable of giving one of these.
Vile Villain, Saccharine Show: The world of That Guy With The Glasses is by no means a happy-go-lucky land, and the special is no exception. But he's still a mar more imposing and sinister villain than you would expect from the site's productions, and a fair larger body count than other villains before the credits roll.
Would Hit a Girl: He's an equal opportunity bad guy. Though in Nostalgia Chick's case he allows a switch for a stunt double, Nella.
Harmless Villain: Ultimately. When you're so pathetic that you make the Critic look competent in comparison, you know you're in trouble.
Hero Antagonist: Jaffers just wants to keep Malachite from the gauntlet and thinks the reviewers aren't worthy guardians. Nevermind that he's blatantly incompetent and that the TGWTG crew massively outnumbers Jaffers' group, which means they might have a slightly better chance of guarding the gauntlet.
Loners Are Freaks: Subverted, he is actually a perfect normal person(even if a little odd due to being from the past), who is perfectly aware Dungeons & Dragons is just a game, and even comments that he started to get suspicious when Malachite seemed to take the search for malachite's hand as real.
What Happened to the Mouse?: When Malachite sends Spoony flying into the air, he eventually falls back on the battlefield. Jaffers, meanwhile, never reappears. Then again, he did get shot up instead of at an angle...
Also, note that Spoony is only finger flicked into the air, while Jaffers is sent flying with a Megaton Punch.
Distinctive Appearances: Despite being dressed identically, it's possible to tell which Cloak you're looking at. The one played by The Last Angry Geek because of his size compared to the other two, and the one played by Iron Liz due to having boobs and wearing gloves (which were actually driving gloves).
Wrong Genre Savvy: On the other hand, they believe the reviewers are honorable opponents...
Help, I'm Stuck!: Covered slides were not designed for husky gentlemen like Cloak 1.
Honor Before Reason: When the battle of the playground is interrupted, the parties find another playground to resume. As the Cloaks take their places, the heroes just leave and make fun of their "too assuming" adversaries.
What Happened to the Mouse?: Cloak 1 flees the field as the Last Angry Geek, but 2 and 3 are unaccounted for at the end. They aren't shown to be killed like Cat's puppeteer and the witch, nor are they shown being knocked away like Jaffers. They just... vanish.
Real Life Writes the Plot: Iron Liz and Linkara's commentary says that while fighting Malachite, he accidentally kicked her in the knee really hard, to the point that she was limping for the better part of a week, so for the rest of the filming of that scene she was inside lying down.
Fate Worse than Death: Promises that this will happen to the Critic and others when she gets fed up with their teasing, saying among other things that Eldritch Abominations from H.P Lovecraft will eat their eyes.
Mercy Kill: Believes she's doing this to The Critic's group.
"Oh, oh dear. Perhaps it's better if you die now rather than wait for what's coming. I know what hunts you, and believe me it's much kinder if I just smash your brains in and drink from your bleeding skull."
Non-Indicative Name: Unless shooting lightning at people and saying they'd be better off dead counts as "Good".
Punny Name: The map refers to her as "Witch Warrior" in order for the riddle to work.
Technically it calls her "Wich Warrior", Jaffers forgot the T.
Dumb Character Smart Actor: Bill, The Stoner who Malachite kills in the beginning, is played by James Troken, one of Doug's college friends. The Spoony-led cast commentary points out that in real life, he's "a doctor and such".
Accidental Misnaming: Doug didn't know the character's name, and wrote him in the script as "Dungeon Master." This resulted in Spoony not realizing that he was expected to film those scenes until the main shoot was over, and Doug asked him to get the shots to him within two weeks.