Henry Masterson, who has an alternate identity called Headmaster, is a disgruntled Sumdac Systems employee with the ability to take control of robots by replacing their heads with robotic heads that he controls. He's a gigantic dork who plays too many video games and seems to have crossed the line between reality and fiction. His vocabulary is littered with slang from the internet, with terms like "n00bs" and "Total ownage!"
The Headmaster's control unit possesses a veritable arsenal of onboard weaponry, with grenades, missiles, and lasers, the latter of which can be used for combat or to decapitate his robot victims. The control unit can also transform from head to bipedal robot.
—The Headmaster...all the time, "Headmaster"
Henry Masterson grew up tinkering with Sumdac Systems robots and got a job as an engineer for them at a relatively young age. His genius caught the attention of his superiors, and he eventually had the honor of presenting his "Headmaster" project, a human-piloted transforming battle suit that could remove and replace the heads of automatons, to Isaac Sumdac himself. The demonstration went awry when the Headmaster unit proved to be too heavy for his robotic test subject, making it collapse and sending its weaponry towards Detroit. Sumdac, incensed by Masterson's plans to put his invention to military use, fired him in a fit of Donald Trump-esque rage.
Masterson apparently absconded with his Headmaster prototype and went off to sulk and play with his Rock 'Em, Sock 'Em Robots. He decided that having his own company would be "wicked sweet", as would exacting his revenge on Sumdac. Needing a robot sturdy enough to support his control unit, he chanced upon a news report on Bulkhead. The emo jerk ambushed and decapitated Bulkhead and subsequently went on a rampage in the Autobot's body.
He demolished several Sumdac police drones en route to a solar power plant. Dubbing himself "The Headmaster", he hijacked local television broadcasts to deliver his ultimatum: Unless he was paid $700 billion, personally delivered by Isaac Sumdac, he would set the solar fusion reactor to overload, which would result in the obliteration of the entire state of Michigan (including Masterson himself). Sumdac arrived in a tractor trailer, accompanied by his daughter, Captain Fanzone, and a small convoy of vehicles. Sumdac offered Henry the money, but the Headmaster grabbed him and announced his intention to take the ransom money and destroy the city of Detroit anyway, then use the threat of future robot attacks to sell his Headmaster units to the military.
When he checked the trailer for the money, he found only the enraged head of Bulkhead. The convoy of vehicles revealed themselves as the Autobots and engaged the Headmaster in combat. After taking a pounding from them, the Headmaster unleashed the weaponry of his control unit. He managed to corner Optimus Prime and began to slice the Autobot leader's head off. Prevented from doing so thanks to an ambush by Bulkhead's severed head, the Headmaster was soon felled by Prowl. Masterson decided to flee, but his flying Headmaster unit was knocked out of the sky by the still-disembodied Bulkhead. With the Autobots distracted by the overloading reactor, the Headmaster transformed his head unit into robot mode and fled.
Once Porter C. Powell took control of Sumdac Systems, he was quick to rehire Masterson in the interest of reaping that lucrative arms market for which Isaac lacked the taste. Powell gave Masterson Sari's bedroom as his office while in the process of kicking her out of it. Masterson was quick to make himself comfortable and started planning renovations to hook the place up for some major gameage. Powell wasn't about to let his employee just slack around, though, and put him to work on a new Headmaster Unit project, even giving him Tutor Bot and Sparkplug to outfit with smaller Units and laser-shooting upgrades.
The Headmaster wanted more than just little bots to tinker with, however, and stole Sentinel Prime's body, upgrading it as well. He would have gotten away with it, but Optimus managed to track him down, defeat Sentinel's possessed body, and take the Headmaster to justice. At least, he was almost brought to justice, until Powell showed up and wriggled his employee out of a legal loophole.
When the Decepticons completed the space bridge that would transport them to Cybertron, Decepticon leader Megatron had Lugnut and Blitzwing retrieve a Headmaster unit from Sumdac Tower to force Bulkhead into helping them repair the bridge. During a battle between the Decepticons and Starscream and his clones, Isaac Sumdac of all people used the Headmaster to body-jack Starscream, only to be decapitated by an unimpressed Megatron. Henry uses the Headmaster unit to jack Starscream's body, only to lose it when he tried to transform. Henry is in jail, again.
The Headmaster unit was recieved by Sumdac when he and Bulkhead were about to make a space bridge using the some parts from it. However, Sumdac's indoor vehicle, the Headmaster unit and the allspark fragment fell down the hole they made when the forklift was overloaded. When Bulkhead went offscreen to search for his buddies, the Headmaster unit, indoor vehicle and allspark fragment formed a new boss of the town.
- Bulkhead (Leader, 2008)
- A non-transforming Headmaster accessory comes packaged with Bulkhead, able to snap into place over the head of the figure and alter its electronic sound and light gimmicks. Once attached, the Headmaster will scream "Ownage! Total ownage!" (in a bizarrely British sounding accent) and all of Bulkhead's lights (normally yellow) turn red. The Headmaster can attach to all other Animated Leader class figures, although Megatron's instructions do not refer to this feature, and the Headmaster does not alter his electronics. In comparison, Ultra Magnus's instructions do call out of the gimmick, but the Headmaster still apparently does not unlock any new sounds or lights. Although the Headmaster on the cartoon takes over Sentinel & Starscream in addition to Bulkhead, it doesn't work with their toys.
- The Headmaster is the first Animated supervillain to escape capture by the end of the episode. Guess he isn't a total loser. He also managed to escape capture in another episode. He wasn't so lucky a third time.
- He's also the first Transformers Animated human character to get his own toy. Well, his invention did at least.
- Like some villains in the series, his real name is a pun on his eventual supervillain name.
- He apparently modeled the face on his Headmaster unit after his own, having his trademark grin and resembling him.
- His Headmaster units are tremendous in weight, even by robot standards, limiting his hi-jacking capabilities to a very small group of Autobots, or Decepticons, strong enough to withstand the weight.
- The size of the Headmaster unit can cause problems with the transforming of hi-jacked Transformer bodies, such as when Optimus goaded the Headmaster into attempting to transform Starscream's body, resulting in the Headmaster unit breaking off.
- Because the Headmaster unit is not a Transformer, its transformation sound is very different.
- After his first attempt failed, Headmaster added an ejectable robotic body so he could escape if things went wrong. Apparently being the reason the Headmaster units were so big, as the unit's head shrank down after the body was ejected.
- Headmaster seems to be the Transformers equivalent of Control Freak from the Teen Titans cartoon, even having the same voice actor, creator, and similar manner of speaking. Although Headmaster's peculiarities are centered around computers, Control Freak's were centered around television.
- He usually speaks in online "slang", such as:
- Calling anyone he doesn't like "N00b" (someone who annoys you, not to be confused with newbie, who is someone who doesn't have any experience playing online).
- Saying "Total Ownage" (dominating or fiercely defeating an opponent online) when he is winning, or has won. Usually when he succeeds in hi-jacking a robot body.
- I believe the proper spelling is "Total Pwnage".
- Derrick J. Wyatt incorporated a number of features common to a number of Headmaster heads into Masterson's robot, although his pointy bits and coloration are a loose homage to Loafer.
- Wyatt stated that the anime series Tengen Toppa Gurren Lagann did not have any influence on the design of Headmaster's head-robot, as Wyatt had not seen the series until most of the first season of Animated was complete. He expressed regret, as in retrospect, he'd have liked to include some of the Gurren Lagann design elements.
- Masterson is every phony Internet tough guy you've ever met.
- Masterson is the only human villain of the series to actually do something evil in Season 3. (Powell produced an army of Soundwave action figures, but having legally acquired the toy's copyrights, he didn't actually do anything illegal.) He is also the very last human villian to appear in the series.
- His headmaster has kibble which is the real face of the headmaster behind his units bot mode.