Skipper is the big guy of a group of penguins. Not matter how ridiculous or impossible the mission seems, he knows what to do and how to pull it off. His information has helped contribute to the wiki. He is the leader of the Penguins of Number Island.
He is a serious penguin, though he likes to joke around. But he is still a nice fellow to meet. He has been seen with his friend contributing to the wiki, and giving himself a low-state profile. We're actually guessing. Skipper like the other penguins is extremely hard to track down, this is what his personality is most likely.
Skipper was born among two other penguins, Kowalski and Rico. Kowalski probably knows the secrets of the Universe, while Rico is just straight-up stupid. They eventually found another penguin to join them named Private. They then took up a job as secret agents and do it very well. So well, that Mr. T himself hired these penguins as his secret agents. Although they used to live in Antarctica, they do their work all around the UnWorld.
During the beginning months of 2019, a series of worldwide attacks came both from the UnWorld, UnUniverse, etc. They were dubbed the World-Universe Attacks of 2019. During those times, a group of unlikely heroes became part of that trope. However, Skipper, Kowalski, Rico and Private were the first ones to be those unlikely heroes.