Oscar (Smiling Friends)

Oscar, also known as Mr. Jester, is the main antagonist in the Smiling Friends episode titled "The Magical Red Jewel (aka Tyler Gets Fired)." He rules over Spamtomia and is Pim's former penpal. Oscar is known for having executed anyone who dared to look him directly in the eye.
His voice is generated using text-to-speech software, specifically TruVoice Adult Male #1. 
== History ==
One day, all of the Smiling Friends are summoned to Mr. Boss's office, where he reveals that he purchased a rare red jewel from the country of Spamtopia. He needs to travel there to retrieve it but admits he doesn't speak the native language, Spamish. Pim mentions that he knows a bit of Spamish, leading Mr. Boss to recruit him as his translator, and the two set off on the journey.
During the road trip, Mr. Boss asks why Pim learned such an obscure language. Pim explains that he's never actually spoken it in person but picked it up from corresponding with a Spamish penpal named Oscar. Mr. Boss then talks about how Spamtopia follows strict traditions and refers to Spamish culture as primitive. When they arrive, the locals sing a song emphasizing their one rule: never make eye contact with anyone.
The two head to a diner to meet their contact, Mr. Jester, and are shocked to find that his head is a giant eyeball. Remembering the rule, they are uneasy, but Mr. Boss greets Mr. Jester, and they sit down. The negotiations for the jewel begin smoothly until a mosquito starts sucking blood from Mr. Jester’s giant eye. As the mosquito bursts a vein, Pim instinctively looks at it to assess the damage, accidentally breaking the town’s one rule by locking eyes with Mr. Jester. The entire diner reacts in alarm.
Pim and Mr. Boss are then taken to a stage where Mr. Jester begins executing people who have looked into his eye by tearing them in half. Mr. Boss offers Pim a cyanide pill as an escape, but Pim refuses and instead asks to speak to Spamtopia's leader. Mr. Jester reveals himself as the leader by removing his executioner’s hood and donning a crown. He lifts Pim, preparing to kill him, but Pim whispers a Spamish prayer. Surprised, Mr. Jester recognizes the prayer as one he created and only shared with a penpal—revealing that he is, in fact, Oscar.
Oscar apologizes for nearly executing Pim and Mr. Boss, explaining that Pim’s letters were a lifeline during a difficult period when he was insecure about his appearance. Pim reassures him that there’s nothing wrong with having a strange-looking eye, even showing his own, and encourages Oscar to embrace self-love. Oscar agrees but still teases Pim about his own eyes, with the rest of the city joining in. Despite this, Oscar pardons them and hands over the jewel.
As Mr. Boss reflects that all cultures deserve respect, he kisses Oscar. In response, Oscar abolishes not only the eye contact rule but all laws in Spamtopia, throwing the country into chaos and causing reality itself to unravel. Pim and Mr. Boss hurriedly escape the collapsing world, but not before a Spamtopian waitress chases after and attacks them. Oscar's ultimate fate remains unknown.
== Personality ==
At first, Oscar is quite insecure, using his role as king to ensure no one mocks him for his oversized eye. After taking power, he established a rule in Spamtopia prohibiting anyone from looking directly into his eye, enforcing it brutally by tearing apart anyone who disobeyed. That said, he remains affable and honorable to anyone who follows his only rule, and doesn't to derive pleasure from harming others unprovoked.
Beneath this insecurity, Oscar is actually a kind and grateful person. When he recognizes Pim as his former pen pal, he immediately embraces him and apologizes, thanking Pim for the letters that helped him during his struggles with insecurity. After this, Oscar officially abolishes all rules in Spamtopia, realizing the wrongs in his actions. Yet, in an ironic and hypocritical fashion, he still mocks Pim for his uneven eyes, unaware that Pim might feel the same pain Oscar once experienced from such teasing.
Initially, Oscar communicated in a gibberish language known as Spamish, native to Spamtopia. However, after Pim accidentally looked him in the eye, Oscar switched to speaking fluent English. 
== Physical appearance ==
Oscar is a humanoid creature with a large eyeball for a head, oversized hands, and a small torso. His body displays a rainbow gradient, and his iris is a vibrant hot pink. He wears a red cape and matching red jester shoes.
Throughout the episode, he dons four different hats: a red and white jester hat adorned with gold bells (his primary choice), an executioner's hood, a crown, and a baseball cap. 
== External Links ==
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== Navigation ==
Category:Cartoon Network characters
Category:Comedy characters
Category:Animated characters
Category:Science fantasy characters
Category:Males
Category:Kings
Category:Villains
Category:Antagonists
Category:Reformed characters
Category:Smiling Friends characters