@whoisme: Well, without prior knowledge of Achilles' weak spot, it's unlikely that Hercules could kill him in battle, despite his massive strength advantage. Achilles' (debatably) superior combat skill and his invulnerability would help him take down Hercules. While Hercules is still exceedingly durable, without knowledge of Achilles' heel he would have no way of putting him down.
As for God Hercules, this fight is more complex. Achilles, of course, has no way to kill God Hercules, but he can definitely still be wounded. In Greek Myth, when a God fought a hero, (namely the fight between Ares and Diomedes, in which Diomedes successfully wounded Ares with help from Athena), they were clearly not as powerful as normal so as to make it a "fair fight." Additionally, God Hercules was a relatively minor god. I maintain that Achilles could wound God Hercules enough for him to relent, thus securing a victory.
I don't know where this came from, but Heracles was worship was widespread and not at all minor. He was usually not considered one of he 12 Olympians, but existed just outside of that grouping. Part of the myths is that when Heracles did go to Olympus, he was offered a Throne and a position among the 12 leading gods, but he refused. If he was offered a spot in the highest grouping of gods in Greek/Roman mythology, we can definitely say that he wasn't minor.
They report of Heracles further that Zeus enrolled him among the twelve gods but that he would not accept this honour; for it was impossible for him thus to be enrolled unless one of the twelve gods were first cast out; hence in his eyes it would be monstrous for him to accept an honour which involved depriving another god of his honour.
1st round- Achilles. He's smarter than Herc imo.
2nd round- Hercules. Not really fair, unless Achilles can phone-a-friend and get Kratos to help.
I also don't know when Achilles ever showed that he was exceptionally intelligent. He was educated like most characters in the myths, but so was Heracles. The issue is that Heracles also has dozens of intelligence feats to go with that. The only people during the Trojan War that I can really see matching wits with him are Odysseus and maybe Nestor.
Erginus then demanded that the guilty party be handed over to him, and Creon, the king of the Thebans, dismayed at the great power of Erginus, was prepared to deliver the man who was responsible for the crime complained of. Heracles, however, persuading the young men of his age to strike for the freedom of their fatherland, took out of the temples the suits of armour which had been affixed to their walls, dedicated to the gods by their forefathers as spoil from their wars; for there was not to be found in the city any arms in the hands of a private citizen, the Minyans having stripped the city of its arms in order that the inhabitants of Thebes might not entertain any thought of revolting from them.
Heracles' speed was also fairly high. He was arrayed against the greatest of the Amazons and was untouchable to them. He was more agile than the swiftest of them and 3 that were companions of Artemis in the hunt and never missed their mark while attacking together could touch him.
Now the general mass of the Amazons were arrayed against he main body of the followers of Heracles, but the most honoured of the women were drawn up opposite Heracles himself and put up a stubborn battle. The first, for instance, to join battle with him was Aella, who had been given this name because of her swiftness, but she found her opponent more agile than herself. The second, Philippis, encountering a mortal blow at the very first conflict, was slain.
Then next, Celaeno, Eurybia, and Phoebê, who were companions of Artemis in the hunt and whose spears found their mark invariably, did not even graze the single target, but in that fight they were one and all cut down as they stood shoulder to shoulder with each other.
In the Iliad, Nestor says that the men that fought in the Trojan War couldn't measure up to the men that he'd known in his youth and the heroes that came before. That's not entirely fair. Peleus was the father of Achilles and Nestor's contemporary. Peleus' wife, Thetis, was destined to have a son greater than his father, so Achilles, the greatest of the men during the Trojan War, could measure up to a decent hero of the past and was probably stronger than Nestor in his youth. However, Heracles exists as an exception. Heracles was by far the greatest of the Greek heroes, to the point that he could battle gods on his own and come out on top or stalemate them. The River God, Achelous, Thanatos, Ares, Poseidon, Hades, Hera, Apollo, Old Age, Nereus and even Zeus have fought him before. The closest he came to defeat was in his wrestling match with Zeus, where he wrestled his father to a stalemate.
When Heracles was finishing the Olympian contest, he summoned any willing participant to wrestle. Since no one dared take up the challenge, Zeus entered disguised as a man, and after a long time – the two opponents being equally matched – he revealed himself to his son.
In the Iliad, Achilles isn't invulnerable, but there are later versions where he is and those are the most popular. The problem is that Heracles has fought multiple invulnerable or conditionally immortal monsters and giants and figured out ways to kill them off, so even if we take that version of Achilles, he's probably going to lose.
Also, on the skill issue, I don't see a reason to assume that Achilles was more skilled than Heracles. He undoubtably was a very skilled fighter and the best of the Greeks at the time, but Heracles was the best by far of a generation of Greeks that were much more godlike on average. When the Argonauts get together, Heracles was unanimously chosen to lead the expedition, but he graciously gave that position to Jason, because he'd assembled the group. He was specifically removed from the story, because all of the challenges the Argonauts were facing would have been trivial if he was there and throughout the story, he exists ahead of the Argonauts. As if they can't reach him.
Untimely Epic - Google Books
The Trojan War takes about 10 years and a 1000 ships, but Achilles still doesn't live to see the end. A generation or two earlier, when Laomedon, the father of old King Priam from the Iliad refused to pay Heracles after he saved his daughter from a Sea Monster (sent by Poseidon, because Laomedon had scammed him and Apollo), Heracles showed up with 6 ships and sacked Troy. It didn't even take him a year.
Heracles wins easily. Even before godhood. With godhood he's also 100% immortal, so that's just not fair (there are also a few examples of him exibiting extra powers as a god, but that's a separate issue). Heracles wins.
Comparing him to someone like Theseus or Atalanta would probably be more fair.
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