The oldest superhero/super-villain rivalry in the Marvel Universe is between Steve Rogers/Captain America and Johann Schimdt/the Red Skull. First coming to blows in the 1940s during World War 2, when Cap was the Allies' greatest hope and the Skull Hitler's top crony, the two men, and their conflict, survived to present day.
Given how long they've been at each other's throats, Captain America and the Red Skull have several battles against each other. Let's find out which ones were the most memorable.
10 Captain America Comics #7
This is where it all began; a Red Skull by the name of "George Maxon" had previously appeared in the debut issue of the Captain America Comics and perished in issue #3, but the Red Skull was just too good a villain to dispose of. Thus came Johann Schmidt, the true Red Skull, in issue #7. This issue follows Schmidt on a murder spree, punishing his minions for their continued failures, while Captain America and Bucky are hot on his heels investigating. Schmidt seemingly meets the same fate as Maxon in the end, but he wouldn't be down for long.
9 Tales of Suspense #79-81
When Captain America returned to print in 1964 and officially became part of the larger Marvel universe created by Jack Kirby and Stan Lee, it was only a matter of time before his arch-nemesis returned as well. Sure enough, in a three-part tale published in Tales of Suspense issues #79-81, the revenant Red Skull appeared. Awakened from suspended animation by members of the terrorist group A.I.M., Schmidt steals the reality-warping Cosmic Cube from A.I.M. and lures Cap to an island, hoping to defeat his old nemesis. Things don't go as the Skull planned, but this would be far from the last battle between the two men out of time.
8 Captain America #293-300
Discovering that his body is rapidly deteriorating to its proper age, the Red Skull becomes alarmed that he'll die with unfinished business; he thus orchestrates what he plans to be his final confrontation with Captain America. Kidnapping Cap, the Skull subjects his arch-enemy to a medical treatment that brings the Captain's body to its rightful age as well, and the two now-aged enemies begin a brawl to the death.
At the denouement of their battle, Cap admits his searing hatred for the Red Skull, but still can't bring himself to kill Schmidt with his bare hands; the Red Skull thus dies unfulfilled, having neither killed Rogers nor corrupted him.
7 Captain America #350
The Red Skull's death in Captain America #300 was only a temporary reprieve for our hero. 50 issues later, it was revealed that after his death, Arnim Zola transferred Schmidt's mind to a cloned body of Captain America. In the visage of his greatest enemy, Red Skull infiltrated the US government with an anglicized alias, John Smith, and has Steve Rogers replaced as Captain America with John Walker/The Super Patriot. After manipulating Rogers and Walker into conflict, the Skull attempts to poison them with his "Dust of Death" but an attack by Walker causes Schmidt to inhale the Dust himself, mutating his face into an actual Red Skull.
6 The Death Of Captain America
As you might've guessed from the title, the Red Skull finally accomplished one of his ultimate goals; killing Captain America. As Roger is being escorted to trial for his actions in Civil War, the Skull (now inhabiting the body of former Soviet Agent Aleksander Lukin) orders Crossbones to fire sniper shots into the crowd, making it appear that he's trying to kill Cap; SHIELD agent Sharon Carter, Steve's longtime girlfriend, then rushes to Cap's side. Thanks to a post-hypnotic suggestion from Dr. Faustus posing as a SHIELD psychiatrist, Sharon shoots Steve in the chest three times. Through this plan, the Red Skull inflicted unimaginable pain without firing a single shot himself.
5 Captain America Reborn
Since the Red Skull has a habit of refusing to stay dead, it only makes sense that his worst enemy would follow suit. Captain America Reborn would reveal that rather than being killed outright, Steve Rogers had been "unstuck" in time, and was constantly flashing between different periods of his life; this was part of Red Skull's plan to transfer his mind to Rogers' body, so as to again have a super soldier body.
Putting his plan to steal Rogers' body into action, Schmidt does briefly succeed in taking control of Cap's body, but Steve, his consciousness still buried deep, regains control before destroying Schmidt's robotic body as well.
4 Captain America: The First Avenger
For Cap's debut MCU outing, depicting his origin and set during WW2, the Red Skull was a natural villain; this version of Schmidt was an early test subject for the same Super Soldier serum that gave Steve his powers, and the film used the contrast between them to demonstrate the different effects being given power can have. In their final confrontation aboard a bomber plane of Schmidt's design, the Skull was seemingly disintegrated when he held the Cosmic Cube (renamed "the Tesseract" for the film), but his actions forced Cap to crash the plane in order to save US cities from the bombs it carried. As a result, Cap's seven decade hibernation was ultimately the fault of the Skull.
3 Ultimate Comics: Avengers #1-6
When the Red Skull made his Ultimate Universe debut, he turned out to be one of the characters most radically reimagined for the new setting. Not Johann Schmidt or an old enemy of Cap, this Red Skull was actually Steve Rogers' illegitimate son, born with his father's super soldier strength but none of his moral compass. Desiring the power of the Cosmic Cube and murdering his way to get it, the Skull was impaled on the nosecone of a jet piloted by Cap himself. Not the best father-son bonding experience, to be sure.
2 Uncanny Avengers: The Red Shadow
After yet another resurrection, the Red Skull turned his interests towards mutants, intending to drum up the pre-existing prejudice against them to gain power. At the same time, Captain America was organizing the "Avengers Unity Squad," a team with members from both the Avengers and the X-Men, in an attempt to gain support for mutants.
Surgically merging his brain with that of the then-deceased Charles Xavier, Schmidt induced anti-mutant riots across New York City, and even attempted to bend Captain America's will to hatred. Cap's strength of will proves sufficient to resist, however, and the Skull is forced to flee.
1 Secret Empire
One of the Red Skull's most devious plots against Captain America didn't even involve violence; manipulating the sentient Cosmic Cube, Kobik, the Skull is responsible for creating a HYDRA sleeper agent version of Cap. Given HYDRA has long been one of Cap's greatest enemies and is antithetical to the values he embodies, this plot by the Red Skull was subversively, ingeniously evil: he took Cap's very identity from him with only a thought.