"The Skids" is a nickname the other residents of Letterkenny give to Stewart's group, who spend time in his basement playing video games and making and consuming drugs, notably meth, or dancing in the dollar store parking lot. Like the rest of the group, Stewart sees himself as a social outcast, and his clothing is influenced by goth/emo subculture.
Katy sees him on the stoop at the clinic and laments the drug use that has led to his ostracism and unattractiveness. She mentions that that in high school, when his interest was music, that he charmed her. This inspires him to quit the meth business and refocus on music to seek her affections, spending the group's drug proceeds on a rave ("Rave"). Although the rave is unsuccessful, he is invited back to DJ at the annual St. Patrick's Day party at the Ag Hall ("St. Perfect's Day").
The Hicks and others simultaneously despise and pity him. He makes enemies of the Natives by reselling cigarettes for profit, against the explicit wishes of Tanis. Reilly and Jonesy similarly seek revenge for giving meth to the rookie and giving Letterkenny a reputation as a meth town. Still, the Hicks and the hockey players team up to defend the Skids when Tanis and the Natives come to donnybrook ("A Fuss in the Back Bush").
Katy and Stewart dated for a brief time, to the consternation of Wayne as well as the hockey players ("A Fuss at the Ag Hall"). The relationship produces friction between Stewart and the other Skids, and set up a rivalry between him and Devon, who takes over leadership of the Skids and evicts Stewart from the basement. Wayne allows Stewart to stay at the farmhouse until he can relocate, but accidentally sees his horn during the stint, which disturbs him.
Stewart and Devon's rivalry spills into the election for Ag Hall president, with Devon producing a campaign video for McMurray and Stewart producing one on behalf of Wayne. Stewart is more interested in beating Devon'a view count than in the election, however; he wins the race for views, but Wayne loses the election ("The Election").
Some time after Devon's departure, Gae joins the Skids and inspires them to mischief, such as vandalism. Stewart organizes the group as a collective calling itself F.A.K.U.: Freaks Acting Krazy United ("MoDeans 2"). Gae's plan to misbehave so badly that her mother takes her back to the big city succeeds, however, leading to a painful farewell ("Bradley Is a Killer").
Stewart also comes into a rivalry with Glen over use of the discount store parking lot, which the Skids want to use for doing rips on their bicycles and which Glen wants to use for street preaching ("Never Work a Day in Your Life"). The dispute falls into stalemate, at which point Stewart asks what Jesus would do, and agrees to "sample His style" ("Way to a Man's Heart"). He concedes that God is "pretty metal" and agrees to share the parking lot.
Stewart continues to feel alienated from the other townsfolk of Letterkenny. He asserts a dislike of his cousins, the Bay Brothers, when they return to Letterkenny for hay season. At the Great Day for Bay celebration at the farm, however, they ask for him, and welcome because he is "family, all the way." While they have no interest in doing rips with Stewart, they agree to rip Chel together ("Great Day for Thunder Bay").
Stewart earned minor celebrity by defeating Katy in the annual Letterkenny Adult Spelling Bee. Katy defeated him the following year, however, reclaiming the crown ("Letterkenny Spelling Bee"). Later, Glen, Gae, and the Skids join and host an intervention for him after he descends into a dark web addiction, and he is sent away to rehab. When he returns, his healthy and clean-cut appearance shocks them ("Back to Back to Back").
Stewart joins Gae in the city, where they DJ at a club, and with Roald, have a side business making and selling GHB—dyed green so that it cannot be used as a roofie. Roald, worried about their involvement in drugs but also envious of Stewart and Gae's relationship, calls the Hicks and asks them to come to the city to fetch Stewart, which they do ("The City").
Stewart and the Skids wear coordinated outfits, mostly in black, reflecting an initial interest in goth or emo subculture. Initially, he wears his black hair long and unkempt. When he visits the Hicks regarding Fartbook, he is dressed in a black T-shirt and black hoodie, accessorized by an upside-down cross on a chain and a dog collar, with black jeans and heavy boots, and with fingernails painted black. His eyes are bloodshot from meth, but this fades when he stops using.
When he is dating Katy, he takes to wearing a white T-shirt, leather jacket, and toque, which the other Skids find repellent. Later, they take to black overalls, which Stewart wears with a black tank top, accessorized with a black bowler hat and black chain bracelets, and still with fingernails painted black.
After returning from rehab, Stewart wears his hair short and dresses in more mainstream jeans and T-shirts, with a more fashionable chain ("What Could Be So Urgent?"). After his return to Letterkenny from the city, however, he reverts to his former style, wearing his hair long and dressing in black.
Stewart develops feelings for "the lady Katy" when they meet outside the Letterkenny Walk-in Clinic, and she laments that his drug abuse has made him unattractive and a social outcast. Inspired by this, he decides to quit the meth business and spend the Skids' money on a rave, coming to the farm to invite her personally. Katy was one of the only people in town to attend, after the event was sabotaged by Devon ("Rave").
She gradually develops feelings for him, being sure to include him when the Hicks and hockey players share a drink after their scrap with Tanis and the Natives ("A Fuss in the Back Bush"). After she breaks up with Reilly and Jonesy, they begin dating in earnest, to the consternation of Wayne as well as Devon and Roald. When Devon expels him from the basement, Katy pressures Wayne to let Stewart stay at the farmhouse. They never become intimate, however, as Katy loses patience with Stewart's immaturity in the relationship (for instance, giving her the "silent treatment" instead of just saying why he is upset), and they break up, breaking Stewart's heart. Katy was later frustrated that they never became intimate after learning of the size of Stewart's horn, and told Stewart that while they were a bad idea as a couple, he's still cool.
Their estrangement reached a fever pitch at the Letterkenny Adult Spelling Bee, an even Katy had won nine years in a row before losing to Stewart. The following year, they again faced off as the two finalists. While Stewart was initially crowned repeat champion, Tanis found that the judge's card was wrong, and Katy had correctly spelled triskaidekaphobia, regaining the title. Katy's presence at Stewart's intervention for drug and dark web abuse was what finally convinced him to go to rehab, and she led the Hicks in rescuing him, Roald and Gae from GHB dealers in the city (though this was in part so she and the other Hicks could enjoy the city's ameneties). As of the end of S6, they appear to be in a friendly place. In S7, Stewart helps Katy with producing “Crack an Ag;” their relationship remains friendly, although Katy maintains a curiosity about the size of Stewart’s horn.
Stewart and Wayne hold disdain for each other, although over time they develop a begrudging respect. Wayne cannot stand the Skids' drug use and general aimlessness in life, and is exasperated when they taunt him for looking at Grindr ("Ain't No Reason to Get Excited"). Stewart is physically intimidated by Wayne, and holds the conventionality and work-centered life of the "shirt-tuckers" in contempt.
The Hicks live by a code; they defend the Skids when Stewart and Devon's double-dealing attracts the ire of Tanis, and he allows Stewart to stay at the farmhouse when Devon expels him over dating Katy ("A Fuss in the Back Bush"). Wayne is very unhappy with that relationship as well, not to mention disturbed when he accidentally sees Stewart's enormous penis during his stay at the farmhouse. While he respects Katy enough not to intervene, he, Dan, and Daryl are hostile to Stewart when he is around, sometimes throwing insults and sometimes baseballs.
Stewart! Fuckin' greasiest skid I ever seen Criss Angel Mindfreak-lookin' motherfucker. — Wayne ("Rave")
That kid is a polished turd. — Dan ("A Fuss at the Ag Hall")
The find common ground unexpectedly, years later, when they encounter each other at MoD3an's on Valentine's Day, when most of the others are at the church for speed dating ("Valentimes Day"). They both decry the crass commercialism of the holiday, and their hatred of jocks, and over beers share thoughts about hockey and other matters, and they go to the hockey arena to shoot pucks. The evening is spoiled, however, when Stewart tells Wayne he did not tip the wait staff, causing Wayne to chase Stewart off the ice.
Stewart and the other Skids are bullied by the hockey players early on, subjected to taunts and intimidation.
Fuck, Lemony Snicket, what series of unfortunate events you fuckin' been through, you ugly fuck? — Reilly ("Ain't No Reason to Get Excited")
Still, at least some of the division seems to be in Stewart's head. He bitterly resents his own cousins, local hockey stars James and Hudson Bay, and does not want to celebrate when they return home for hay.
I'm nauseated by their hokey hockey hickey shit. — Stewart
When they encounter each other at the farm, however, they are the ones who have been seeking Stewart's company, and they agree to spend time ripping Chel together ("Great Day for Thunder Bay").
Reilly, Jonesy, and the other Letterkenny Shamrocks did show up to Stewart's rave, but were prevented from entering when the Coach sees them in line and sends them home. Their open hostility mainly relates to Stewart's activities getting Letterkenny labeled a "meth town," and for the Rookie using meth. They show up at the basement planning to trash it and to beat up the Skids, only to find that Tanis and her crew have already trashed it. Eventually, they join the Hicks to defend the Skids against Tanis and her crew, and all have a drink together at MoDean's afterward ("A Fuss in the Back Bush").
Reilly and Jonesy never really become friendly with Stewart, though they are no longer openly hostile except when Stewart arrives at the farm at the same time they do, and with the same goal: to win back Katy ("Finding Stormy a Stud"). For the most part, they live in different worlds, and rarely interact directly. When Katy starts dating Reilly monogamously, Jonesy is left on the outside, and is tempted to join up with the Skids, but Reilly returns to rescue him from that fate ("A Fuss at the Golf Course").
Reilly and Jonesy do come to the basement, however, when they feel their progress in the gym has plateaued, and need a "quick half cycle" of steroids to jump-start their gains. Stewart informs them of the various side effects associated with "juicing," but quickly assures them "but you guys should be good" when they start to have second thoughts. Roald accidentally gives them Ritalin, however, and "Rits, not 'roids" turns out to be all they needed ("The Letterkenny Leave").
Gae is more or less Stewart's soulmate, sharing his nihilistic view of the world. They meet and bond in S3, where they form F.A.K.U. and commit various acts of vandalism while dressed as clowns to get Gae sent back to the big city. The plan works, but Stewart and the Skids are depressed once Gae leaves. In S5, Gae returns for Stewart's intervention and smiles upon seeing the rehabilitated Stewart. In S6, Stewart is living with Gae in the city along with Roald, selling green GHB and enjoying creative sex. However, they ignore the threat of existing GHB dealers and mostly focus on correcting the poor grammar in their threatening notes. When the Hicks, summoned by Roald, show up to deal with the GHB dealers, Stewart and Gae are shocked when the dealers produce knives for the fight, but the green GHB customers save them by beating up the regular GHB dealers. Realizing things have gotten too hot in the city, Gae tells Stewart to go back to Letterkenny while she'll head elsewhere for now; based on the longing looks each sneaks at the other as they part, there are still strong feelings there. Stewart continues to miss Gae in S7, prompting a large number of double entendres as the Hicks ask him about what he misses about “Gae sex.”
- → See 42 images of Stewart at Images of Stewart.