Sideways is the consummate con-artist. He is misleading and deceitful in everything he does, and he lives for the look of shock and betrayal on his victims' faces when they realize he's played them for fools. When the displaced population of Planet X allied themselves with Unicron to avenge themselves on Gigantion, this treacherous nature made him the perfect robot to pull off the ultimate act of treason - an attempt to sow confusion between Autobot and Decepticon to prevent them from uniting to oppose his dark master.
We're still not quite sure what the heck he actually is.
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Sideways first appeared as a beam of light from the sky striking a large Earth city near the Autobot base. An enigmatic warrior, he appeared to side with the Autobots, helping Hot Shot by watching his back during a confrontation with Scavenger. When asked to reveal himself, he transformed, his rider quickly splitting and becoming a helmet that covered his entire head. He claimed to be Sideways, a drifter who just wandered into the conflict. While he gave the human kids Billy and Fred rides in cycle mode to keep them entertained, Hot Shot and Red Alert as well as Rad and Alexis were suspicious of the motorcycle's motives, especially his close attention to the Mini-Cons. Gale
In the following battle, Megatron faced Sideways and Hot Shot alone, and managed to force the Mini-Con panel Sideways had (apparently) found out of his grasp. As the Decepticon leader began to warp away, both Autobots grabbed onto Megatron and all three were teleported to the Moon. To Hot Shot and Megatron's surprise, the Mini-Con panel was a fake, made to convince Megatron to retreat so that Hot Shot, spurred on by Sideways' encouragement, could defeat the Decepticons once and for all. Though both robots fought well alongside each other, with Sideways' expressing concern over Hot Shot's well-being, he eventually betrayed the young Autobot, by striking a deal with Megatron. He would pretend to be Megatron's hostage and in exchange, no matter what, Hot Shot would turn over the Star Saber sword. At first, Hot Shot did follow through, but reneged at the last moment by calling the Mini-Cons back to him. Sideways suddenly attacked Hot Shot, knocking the Star Saber out of his hands and kicking it to Starscream. He switched Mini-Con heads, revealing his allegiance to the Decepticons. Hot Shot was savagely beaten by the Decepticons, who stopped short of destroying him on the advice of Scavenger, who teleported the young 'bot back to the Autobot base. Once Sideways' loyalty to the Decepticons seemed to be confirmed, he began manipulating them and playing them against each other to suit his mysterious goals. Credulous
One of these goals was the replacement of Megatron as Decepticon leader after a series of significant losses. Sideways sowed the seeds of rebellion within the Decepticon ranks, subtly turning Starscream against Megatron and convincing Megatron of Starscream's imminent treachery. The situation came to a head when the two Decepticons fought outside their base, but Sideways then realized Megatron would never execute Starscream for his insubordination, exposing an ever-constant weakness within the Decepticon command structure. After the battle, Sideways mused that this weakness would come back to haunt Megatron one day, and would be his ruin. Fortunately though, this incident somehow served to solidify the Decepticons as a unit, giving them much greater morale and cohesiveness, and achieving Sideways' aims of giving neither faction in the conflict a clear advantage. Rebellion
Shortly thereafter, Sideways tried to hack the Autobot base computer, only to encounter the children attempting to destroy the equipment to stop Sideways. He transported them to a digital universe, where they saw the coming of two new combatants. He tried to threaten them into handing over the Street Action Mini-Con Team, before the kids realized that as this wasn't real, he could not harm them. Sideways then apologized to an unseen master, shortly before the children escaped the digital universe, chased by an unknown entity. Chase
The Decepticons began to distrust Sideways, suspecting he was not what he seemed, and realized he was manipulating everybody in the unit. Caught out by Thrust and the other Decepticons while communicating with his unseen master, Sideways panicked and attempted to escape, but not before he was confronted by Megatron and sliced in half with the Star Saber sword. Sideways simply reformed each time, reconnecting his parts and absorbing laser blasts from the other Decepticons. Megatron, in fury and disgust, hacked Sideways to pieces and he was seemingly destroyed... or so they thought. Sideways had entered trans-phase mode, rising in the form of a twisted nanite creature before the Decepticons' eyes, declaring that the Star Saber sword and Skyboom shield were merely toys to him, as he was near-invincible. He said there were millions of Mini-Cons left to be found, and challenged Megatron to see who would find them first, before flying off to parts unknown. Detection
After his "demise," he would return frequently on computer screens through trans-phase mode to continue his mysterious goals. He convinced the Decepticon Thrust to secretly betray Megatron, and gather the three legendary Mini-Con weapons - the Star Saber, Skyboom shield and Requiem Blaster in order to revive the planet-eater Unicron.
As Unicron revealed himself to the people of Cybertron Sideways himself was revealed to be a puppet of Unicron, and ultimately was destroyed by the Requiem Blaster, wielded by Optimus Prime in a battle in Unicron's core. Origin
Sideways made his return two decades later, as a faction-swapping agent that chose to manipulate those who'd recognize him in secret. He latched onto Starscream, who had no memory of the Unicron Battles, and manipulated him into obtaining the Omega Lock.
Sideways' long-term plan was to now avenge the destruction of his race from eons ago using the power of Primus. He and his partner Soundwave shared the common goal of destroying the Giant Planet.
As mentioned in the Planet X biography, servitude of Unicron eventually drives one to insanity or loss of self. Sideways seems to be suffering from this effect during the Cybertron story.
Nobody seems to remember Sideways for some reason. You can chalk that up to the Unicron Singularity. Yoink! (The Ask Vector Prime forum on Transformers.com notes that Sideways was preserved by Unicron's dark power after Armada.)
Sideways was first seen working on a secret desert rocket site, guarded by Skywarp and Wheeljack, which was designed to launch a laser system in orbit. After the rocket was launched, he returned to Cybertron, and was present for the battle against Unicron... though what exact role he played in it is unknown.
(The Dreamwave "More Than Meets The Eye" profile book for Armada did list Sideways as a mysterious ninja, and a herald to Unicron. It is suspected that he was simply functioning as a sleeper agent in the mainstream DW Armada comic.)
A MYSTEEERIOUS motorcycle Transformer going by the name "Doubleface" (Armada Sideways's Japanese name) appeared in the Robot Masters saga. This Transformer had a special communications system called "Shadow and Bright."
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