Skyler makes his first appearance in which his girlfriend, Shelly Marsh, is baby sitting Eric Cartman, and she invites Skyler over. Due to the abuse that Shelly puts him through, Cartman tries to expose Shelly as being a bad babysitter. However, each attempt fails, and results in Cartman being beaten by the couple. Later, Shelly allows for Cartman to watch the meteor shower with her and Skyler, who tries to push Shelly into having sex with him. Shelly refuses, causing Skyler to become furious and to dump her immediately, while claiming he has other girlfriends who would put out for him. Showing an uncharacteristic show of concern and pity for the heart broken Shelly, Cartman helps her get revenge on Skyler, by distracting him, allowing Shelly to destroy his guitar, put it in a litter box with a message calling him the "King of Turds", written in cat poop. Infuriated, Skyler goes back to Cartman's House with an intent on attacking Cartman and Shelly. However, Cartman's cat, Mr. Kitty, was having an orgy, and Cartman throws catnip at Skyler making all the aroused cats jump upon him and attack him, even taking off his underwear in the process.
Skyler makes another appearance, a season later, in "Timmy 2000", where he is seen playing a prominent role. Timmy randomly meets up with Skyler and his band, The Lords of The Underworld, in his garage. Hearing him scream his catchphrase "Tim-ah!", Skyler asks Timmy to join his band and so that they can win the battle of the bands. Skyler's band wins, allowing them to open for Phil Collins at Lalapalalapaza. Phil Collins, however, is disgusted by the idea of Timmy being exploited and being mocked, and gets Skyler to become jealous of Timmy, for getting all the recognition. Skyler quits his band, causing it to disband, and Collins allows him to perform in his own solo band, called Reach for the Skyler, at Lalapalalapaza. During Lalapalalapaza, Phil Collins is booed off-stage, because no one really likes his music or his attitude towards Timmy. Feeling guilty because of his earlier decision to quit his band, Skyler returns to the band, who agrees to take him back.
He makes a brief appearance in "Christian Rock Hard" in the crowd of striking musicians.
Skyler wears light teal pants, a white shirt, red shoes, a black jacket, and a blue hat. He initially has a brown acoustic guitar in "Cat Orgy", but in "Timmy 2000", he uses a white electric guitar.
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Skyler trying to kiss Shelly.
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Shelly breaking up with Skyler.
Skyler and his band playing Shelly's song.
Skyler performing with his band at Lalapalalapaza.
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Skyler asking Timmy if he can be back in the band.
Skyler is extremely self-centered and only cares about his guitar in the episode "Cat Orgy". This is again demonstrated in "Timmy 2000" in which he bullies his friends Jonesy and Mark into continuing with a band that has repeatedly failed. However, he later comes off as somewhat nicer when he demonstrates concern about his band and feels guilty for being a jerk after quitting the band when he doesn't receive primary attention. Skyler's romantic or rather sexual feelings towards Shelly demonstrates that he is technically and legally a pedophile due to the 9-10 year age difference between them.