Here we have the one of the biggest villains of world war 2, and ally of Hitler, Johann Shmidt A.K.A. Red Skull.

After his mother was murdered by his father, and said father comitting suicide, so was he adopted by a jewish shopkeeper and fell in love with his daughter, Esther.
But when Esther rejected Shmidts proposal of love, he in unthinkly fury murdered her.
After realising what he has done, so did Shmidt flee in horror, but also felt ecstatic joy in his first murder
Later on he became a bellboy at a hotell, but Hitler saw some opportunity in Shmidt and convinced him to join the Nazi party, got a lifelike red skull mask (thereby his name) and became one of their best soldiers and battled Captain America, Namor, and the original Human Torch (who was an android, and not a human).

He made another Nazi officer, Baron Von Strucker to go to Japan and start an organization, which would be known as Hydra. But Von Strucker broke his ties with the Skull and became the leader himself of Hydra.

Sometime after the death of Bucky, and Captain America got frozen in the arctic after stopping the Red Skull's plans, so did he go off to a suspended animation by an experimental gas in his bunker.

In present day he came back to unleash his evil schemes on the world and opposed Captain America and the Avengers.

He was supposedly killed by the Winter Soldier (who in turn turned out to a brainwashed Bucky), but it was all a ploy so he could do his ultimate plan, which the Avengers fought valiantly against and got the Red Skull killed once and for all.

But later after the Avengers vs. X-men event, so did a clone of Red Skull awaken from a laboratory and see what has happened and saw that mutants were to dangerous and therefor started his own group of mutated humans (using magic and technology instead of genetics) who he calls the S-Men.
And he dug up Dr Xavier's grave to take his brain and gain his psychic powers. These events effectively made him an enemy of Magneto.

Appearances in animated series and voice actors:
The Marvel Super Heroes - Paul Kligman
Spider-man and Spider-man and his Amazing Friends - Peter Cullen
X-men - Cedric Smith
Spider-man the animated series - David Warner, and then Earl Boen
Super Hero Squad - Mark Hamill
The Avengers: Earth's Mightiest Heroes - Steven Blum
Avengers Assemble - Liam O'Brien
Phineas and Ferb: Mission Marvel - Liam O'Brien
Lego Marvel Super Heroes: Maximum Overload - Chi McBride
Marvel Disk Wars: The Avengers - Kiyokawa Motumo

Apeparances in live action movies and actors:
Captain America - Scott Paulin
Captain America: The First Avenger - Hugo Weaving

And I noticed that the picture would look empty, so I added Arnim Zola as a bonus.