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WEBWORLD (Season 3, Episode 16)
Transformers' third season is known for having some of the most "out-there" scifi concepts as the basis for its storylines. But few of them are stranger than this one, which asks the burning question: "What if Galvatron (aka Megatron: Mark II) had the Jack Nicholson part in One Flew Over The Cuckoo's Nest?"
A recurring subplot throughout the season is that Galvatron is losing his mind -- and not just in the figurative sense. Distraught, his Decepticon lieutenants opt to drop him off on a small planet that's been converted into a gigantic intergalactic mental-hospital by a race of aliens who specialize in psychotherapy.
No, for real. That's the actual premise of an entire Transformers episode. It doesn't go well, for the record. I'd like to see this as the subplot of one of the movies, but instead of the blue monkey guys a Transformer therapist voiced by Woody Allen or Dr. Katz.
A DECEPTICON RAIDER IN KING ARTHUR'S COURT (Season 2, Episode 24)
Time-travel! Now there's something that might be fun to play with in this franchise!
Think of this as a thematically "lighter" counterpart to The God Gambit: Two small groups of Autobots and Decepticons are zapped back in time to medieval Europe, where they're taken for "strange knights" and Starscream (because it is always Starscream) sets himself up as a feudal lord. It's one of the "funny" episodes, but it's a cult fave owing partly to its weirdly quasi-realistic take on medieval times and pseudo-science. The Decepticons first order of business is teaching the humans how to build makeshift electrical generators, the "magic spells" wielded by a Gandalf-esque wizard turn out to be differently-named achievements in chemistry, and the supposed "epic clash" of good and evil lords is basically a trumped-up misunderstanding between feudal landowners that the Autobots inadvertently help bring to a peaceful conclusion. On the other hand, there's an actual dragon, so...
But c'mon, would it not be cool to see Transformers stomping around more-or-less Middle Earth? It worked out pretty memorably the last time Michael Bay played around with fairy-tale imagery...
FIVE FACES OF DARKNESS (Season 3, Episodes 1 - 5)
This five-part episode was both the debut of the series' radically-changed status-quo following Transformers: The Movie and also that film's de-facto lower-budget (its animation/continuity errors are the stuff of legend) sequel. Of primary concern: It expands on the deeper-mythos of the Transformers to previously-unprecedented degrees by expanding on The Quintessons, five-faced mechanical eldritch horrors introduced sans-explanation in the preceding film.
Short version: The Quintessons are a more-ancient-than-ancient race of mechanoids that created the ancestors of the Autobots and Decepticons as a slave-labor force on ancient Cybertron. Mistreatment of their creations led to a rebellion and eventual Quintesson exile, followed by their eons-later re-emergence in the wake of Unicron's destruction.
While the Quintessons have never been explicitly mentioned in the live-action films, Lockdown -- the leader of the new third faction of robot antagonists in Age of Extinction -- claims to be acting as a kind of intergalactic repo-man for the Transformers' previously unheard of "creators." So it feels like a safe bet that they or something like them is planned as a possible route for the next movie.
THE REBIRTH (aka AMERICAN HEADMASTERS)
Okay. History lesson time.
Transformers didn't actually get a proper fourth season. Instead, what's often called "Season 4" by fans is actually a three-part episode (set sometime after the resurrection of Optimus Prime at the conclusion of Season 3) called "The Rebirth" that feels like the launch of new season in that it introduces about 30 new characters, brings the "war for Cybertron" story to a close and sets up an entirely new conflict and status-quo that could have continued on into further episodes... but instead just serves to explain the existence of the (then) most-recent run of new toys: The Headmasters (their heads would detach and transform into smaller humanoid robots that would "pilot" the rest of the body in vehicle-form) and Targetmasters (same deal, but their weapons became the pilot instead).
While "Generation One" Transformers continuity actually continued in Japan for several more seasons/series beginning with a more "straightforward" conception of The Headmasters as a new team of Autobots who gradually took up leadership roles among The Autobots (Optimus dies again!); the American (non)launch of the characters was significantly more ambitious and bizarre.
In "The Rebirth," a group of the (unexplained) new Autobots, along with Arcee, Hot Rod and Daniel Witwicky (Spike's annoying son from The Movie,) get involved with a group of humanoid aliens in a state of war with mechanical enemies of their own. Through a series of bizarre complications (and a prophecy about a Cybertronian Golden Age) the good and evil aliens both decide to form allegiances with the Autobots and Decepticons whereby the Transformers will allow their heads to be converted to transform into suits of power-armor to be worn by the humans/aliens, allowing them to merge into organic/machine hybrids: The Headmasters.
Spike himself becomes the head of Cerebros, who in turn transforms his entire body into another even bigger head for Fortress Maximus -- the most absurdly-enormous original Transformer toy of all -- while Daniel sustains battle injuries that necessitate him permanently becoming Arcee's Headmaster partner. Because obviously, there will be no uncomfortable issues whatsoever down the road for a 10 year-old boy having to live as the head of the Transformers' sole female member.