Not much is known about Skipper's early life, as he has not revealed matters related to it in the movies or on the TV show. However, he has revealed that - due to as-yet-unspecified circumstances involving explosions, a high-speed chase, and Hans the Puffin - he is unable to set foot in Denmark after being declared Public Enemy Number One.
Skipper also mentions in the episode "Mr. Tux" that he once woke up in Kyoto on a bed of counterfeit Deutchemarks. This must have been many years ago because Deutchemarks are no longer in use.
Another of Skipper's enigmas is the two former penguin agents Manfredi and Johnson. Skipper has mentioned them on many occasions. They died under unknown circumstances. The only reason for this is that Skipper changes the reason every time he talks about them, so they may exist only in Skipper's demented little mind. He is also arch-enemies with the mad dolphin super villain 'Doctor Blowhole', although the circumstances under which they formed this entity are unknown.
Also a supposed fight versus Hans prevents him to travel to Denmark, although he doesn't mention the reasons. Also unknown is how he got to the Zoo in the first place, or how he met Kowalski, Rico, and Private.
As leader, Skipper was the mastermind behind a plot to escape the confines of the zoo and leave for Antarctica with three other penguins as his accomplices. As it were, Skipper and his troupe of penguins dug and dug under their enclosure until they reached the enclosure of Marty the zebra, thinking it to be the South Pole. Skipper explained to Marty that they would escape the zoo on the grounds that penguins don't belong in captivity and with that, ordered his accomplices to continue tunneling. Late that night, Skipper and the other penguins were caught by a SWAT team, as were six other animals also found outside the zoo. The penguins were tranquilized and put into a crate to be transferred.
When they awoke, Skipper was confused at the lettering on the crate where they were held and ordered a nearby chimpanzee named Mason to read it, with Mason's companion Phil reading it: they were all bound for a wildlife preserve in Africa (this is not logical as African habitat is not for penguins, but some think that Africa was simply the first stop, and Antarctica was going to be a later stop). Skipper ordered Rico, another penguin to pick the lock on the crate where they were held, whereupon the four penguins knocked out the crew and took command of the ship, commandeering it to reach Antarctica. Skipper and his mates finally reached Antarctica and were sorely disappointed by the barren, desolate terrain.
Skipper had the ship return quickly from the South Pole where it crashed into the beaches of Madagascar and a much warmer climate. Upon arriving, he and the other three encountered Gloria and Melman, and saw that Alex and Marty (known as their "monochromatic friend") were gone. Skipper decided to help rescue Marty from the grim fate of being eaten by the native fossa. (Possibly as gratitude for his silence regarding the escape.) It was Skipper who helped to distract the fossa while Marty was recovered and then helped fight off a number of them.
Skipper noticed later on that Alex was still hungry, not being able to eat steak, and had Rico prepare fresh slices of fish in the form of sushi for Alex. Skipper then relinquished control of the ship to Alex, as he no longer needed it, and proceeded to sunbathe on the tropical beaches in comfort. Skipper was asked by Private, one of his accomplices, if they should tell Alex and his friends that the ship was out of gas. Skipper declined, telling his troupe to "Just smile and wave boys, smile and wave."
In the sequel, Skipper leads the penguins in first salvaging a crashed air plane to fly back to New York and then fixing the plane when it crashes at Africa with the help of "more thumbs"(chimpanzees that also escaped the zoo). At the end of the movie, he marries a bobble head. Then the penguins and the chimps fly off in the newly-fixed plane with the diamonds and gold the animals found while finding water.
Skipper is a hardened commando-type, and the leader of the squad of penguins. He often acts like a 'Nam veteran with regards to some kind of Post-Traumatic-Stress-Disorder, especially with regards to his raving paranoia (which even the other penguins sometimes consider as being over-the-top) and conflicting stories of past events. He believes that a friend is just an enemy who hasn't attacked you yet. Thanks to his training in commando skills, he seems to have absolutely no idea of how to act like a real penguin, with Private having to give him advice when he's under close observation by humans.
Of the four penguins, Skipper is the best at hand-to-hand combat, generally able to take down even their surprise attacks. However he has a tendency to overestimate his own abilities, taking on opponents many times his own size, and continuing the attack even when it's shown to be totally ineffective. He claims to not know the meaning of the word 'surrender' and always has trouble admitting fear of anything.
Skipper cannot stand hippies, as seen in Night and Dazed, It's About Time and Hello, Dollface, and would very much like to either beat them up or make them get jobs. He also has Trypanophobia (Fear of needles) as shown in Needle Point and Love Hurts.
He's a 50's style male chauvinist, believing women are weak and need protecting. He's also rather xenophobic, with the opinion that any species other than avian (especially mammals) is inferior. All of this ties in with his raving paranoia, and the other penguins don't always back him up on these points. It has also been stated that he has a fragile ego.
- Needle Point: Skipper started to panic when a visit to the vet revealed that the penguins were getting an injection. A frightened Skipper ran off, but was convinced to come back when Private was taking Skipper's place. Learning that the shot would make him sick (or worse) ( the worse part must mean that Private will die) , Skipper reluctantly takes it.
- I Was a Penguin Zombie: After Skipper breaks his wing, the vet applies a topical cream to ease his pain. The cream has a slight sedation side effect, and this makes Skipper a bit loopy. As he escapes, a movie is played, and this makes Kowalski, Private, and Rico, believe that Skipper became a zombie. Skipper manages to come back to his senses, but the remaining three still don't believe him, and all end up breaking their wings from a fall.
- Out of the Groove: King Julien's antics result in Julien getting his groove stolen. Desperate for help, Julien seeks the assistance of the penguins to get his groove back. But when fighting over the jar that contains his groove, it breaks and enters Skipper's body, and he starts dancing (even doing the moonwalk). The baboons will only help if King Julien apologizes, but given his stubbornness he still refuses to apologize. Skipper has to make Julien apologize by dancing all over him, surprising the rest of the penguins and lemurs speechless to the point where Private says that he wants to cry (this is significant, since penguins don't cry) because Skipper's dancing is so perfect, yet strange. The King's groove is later returned, and Skipper is left to wonder what made him dance until Private thinks he has a little dancer inside him. Skipper says, "Magic's real. Case closed."
- Miss Understanding: A small malfunction during a DNA test causes Skipper to believe he's a girl. After failed missions, Skipper then leaves the penguin's habitat to go visit Marlene and see what it's like being a girl. Marlene is very annoyed because of Skipper's small-minded attitude to what being a female is about - and especially because he hasn't changed at all, but thinks that just because he is a female he is no longer any good at being a commando. She takes Skipper to see the lemurs and save them from the wires. Then Rico, Kowalski, and Private show up to save the lemurs, but end up getting stuck too. Skipper, believing that he is a girl, decides that the mission is not ladylike enough. Eventually, Skipper decides to take off his pink bow and makes an impromptu whip/dance ribbon. After that, the penguins take Skipper to do the test again and find a broken fuse. After they replace the fuse, the machine draws a vertical line through the minus sign, completing the plus mark and proving that Skipper is a boy. Foolishly, Kowalski gave the machine an optional beak-shiner, thus hogging more power. Marlene then becomes sad, hoping Skipper could be her friend. Skipper then put a flipper around her, talking about Alice "Well she's a mammal, everyone knows they're all morons" and Marlene gives him a nasty look and is insulted.
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