Beautiful Animation
The Good: I love your artistic style. The animation is superb and the music went well with the opener. The best part of the animation was when they randomly ran into something, the music stopped, and pirate just fell ragdoll style onto the deck.
Room for Improvement: The script and comedic timing were probably the weakest parts of the short. Clever concept (the arrogant, insecure, awkward octopus/kraken), but just wasn't terribly funny as it was mainly just dry dialogue toward the end. I think what most people find funny on the net is random, unexpected turns, which is what the slamming-into-nothing part was. After that nothing was unexpected or caught me off guard. I was waiting for the conversation to abruptly take a weird turn or for a pirate tor randomly throw a harpoon into the octopus' head, but it never happened.
So, all in all, fantastic artistic style, but work on the script a bit. You've got a lot of potential!