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Red Skull was introduced in Captain America Comics #1 (March 1941), written and drawn by the team of Joe Simon and Jack Kirby. Though later it was revealed that this Skull was an impostor named George Maxon, who was only an agent of the real Red Skull, Johann Schmidt who made his first "official" appearance in Captain America Comics #7 (October 1941), by writer France Herron and the same team of Jack Kirby and Joe Simon. The Red Skull was a Nazi officer, closely associated with HYDRA terrorist organization who fought Captain America numerous times, not only during World War II but also in modern times.
His first animated appearances were on the Marvel Super Heroes Show, which aired in syndication in 1966 and featured five of Marvel's superheroes starring in their own series each one consisting of 13 episodes (separated into three 7-minutes long segments). This show had very limited animation, and was composed almost entirely of actual comic book panels with a voice-over; basically an early version of today's motion-comics. The Red Skull (voiced by Paul Kligman, who also voiced various other characters on the show, most notably General Ross in the Incredible Hulk segments) is featured in the Captain America segments; he appears in a total of four episodes and is one of the few recurring villains on the show - the only other recurring villain being Baron Zemo who appeared in only two episodes. The first episode to feature the Red Skull was the series premiere, entitled "The Origin of Captain America". The first act of the episode obviously shows how Steve Rogers became Captain America, while the next two acts feature the Red Skull's plot to take out certain high-ranking people in the US army and sabotage some of the army's newest weapons. Cap manages to track him down and save his latest target, but the Skull manages to escape, leaving behind a list of the people he was targeting - and the last two names on it are Cap and Bucky. What is interesting is that the comic book this episode is based on actually featured George Maxon, the impostor Skull. The show doesn't mention anything about this, possibly because of time constraints or trying to make the episodes less confusing and I guess only comic fans (or people who research stuff like this online, like me) would really know the difference. In the end, it doesn't even matter - it's just a little bit of trivia I figured would be worth mentioned.
The true Red Skull appears in the next episode, "The Sentinel and the Spy" (please note that I'm only using the title of the first act as the titles for these episodes; it's easier than typing 3 different titles for each episode - though it would make this article seem longer!). In the first act of this story, Red Skull plans on using one of his agents from a prisoner of war camp to steal Project Vanish, a new secret weapon that can disintegrate pretty much anything. The spy is easily defeated by Cap, who tricks him into using the experimental weapon at full power, which causes the gun to explode. In the next part of the episode, the Red Skull's soldiers attack the ship Cap was aboard, and manage to capture him. Red Skull would later explain his fantastic origin to his captive: the young boy who would one day become the Red Skull was an orphan who lived on the streets and had to steal to survive until one day when he managed to find a job as a bell hop for a hotel. There he was noticed by the leader of the army that took over his country (in the original comics, it was Adolf Hitler himself, but here the character remains unnamed) who realizes the boy has potential to become, after some training, his greatest soldier. After months of training he received the costume and title of the Red Skull. A figure, that even his former superiors would come to fear. The final act of the story reveals that a doctor working for the Skull has drugged Cap, making it easier for the villain to brainwash the hero into doing his bidding. Cap is then ordered to seek out and murder the supreme commander of the Allied armies. Cap does as ordered and breaks into the commander's office but as he is ready to assassinate the commander he snaps out of his brainwashing.
Somewhere between the above episode and the Red Skull's next appearance, the setting of the show changed and a time-skip of about 20 years occurred (consistent with the comics the show was based on, and somewhat consistent with the age the show was originally aired, as WWII ended in 1945 and the comics and show took place in the mid 60s, but this little fact really dates the show today, as it's close to 70 years since the war ended). The Red Skull wasn't involved in Cap's origin in this version - Cap and Bucky are attempting to deactivate a plane drone that explodes and apparently kills Bucky and throws Cap into the freezing waters of the North Atlantic, where he is frozen but manages to survive in suspended animation. Once thawed out, he joins the Avengers and keeps fighting against evil all over the world.
Red Skull can be seen in a flashback sequence in the episode "The Sleeper Shall Awake". The episode depicts the final confrontation between Cap and the Skull, during the last days of WWII, where even defeated the Skull mentioned that 20 years later, his followers will continue his plans of world domination. In present day, Cap discovers that three former agents of the Skull have released the Sleepers, three giant destroyer robots - one having a "normal" appearance, one looking like a giant devil bat, and the final one resembling the Skull's head - which all combine together into a single robot that wreaks havoc throughout the country. Cap suspects the head of the robot is a giant bomb, and tries to stop it before reaching its target, apparently the North Pole where it is programmed to fire a blast deep into the planets core and cause the entire Earth to explode. Cap manages to land on the robot's head and change it course, making it explode over the ocean, saving the world.
The last episode of the series is titled "The Red Skull Lives" and explains how the Skull has managed to survive his last encounter with Cap, 20 years earlier. It turns out that he was buried alive in a collapsed bunker, but he managed to survive in the space between two heavy pillars, which held the wreckage from hitting him. On top of that, an experimental gas that was held in the bunker spread throughout the building, keeping the Skull (and two of his men, who were also trapped there) alive in suspended animation. Years later he was rescued from the ruins by scientists from the organization AIM. Seeing that they have similar goals - world domination - Red Skull makes a deal with AIM, and is given a hypno-helmet which he uses to make Cap think he has gone mad by hypnotizing people into not seeing the villains he fights on the streets. Not wanting to share the world with anyone else, the Skull uses his new-found hypnotizing powers to control the leader of AIM into giving him their newest invention, the Cosmic Cube - a weapon which can convert thought-waves into material action. With this new weapon Red Skull can become ruler of the world; he plans on enslaving the entire human race and force them into building new and even more powerful weapons which he would later use to conquer the entire universe, creating an all-powerful galactic empire he would rule. Cap confronts him on his island headquarters but is unable to defeat him now that he wields the powers of the Cube. Red Skull is however defeated when Cap manages to trick him into letting him live, only to become his servant. Once he is close enough to him, Cap defeats him and manages to remove the Cube from his hand. The Red Skull tries to regain his weapon but a landslide makes both him and the Cube fall into the sea, where he apparently is buried alive by the rocks that fall on top of him.
All in all, Red Skull's first animated appearances were pretty good - the stories are more or less faithful adaptations of the classic comics, and I find them entertaining enough. And this was only the start of Red Skull's career in animation.