Gregory transferred to South Park from Yardale, where he purportedly maintained a 4.0-grade point average. He appears in South Park: Bigger, Longer & Uncut. Unlike other characters, Gregory does not appear in the original TV series.
Gregory, who is portrayed with both an upper-class English accent and stereotypical traits of the English, has caught Wendy Testaburger's romantic attention and became in a relationship with her. Wendy denies this to Stan Marsh and kisses him instead, later implying that her feelings for Gregory were merely a strong admiration and never cared for him.
Along with him mentioning he has a 4.0-grade point average, he is a very independent leader to the schoolchildren and has guided them over.
Gregory has quite a singing voice as shown in the song "La Resistance".
He has thick, curly blonde hair. He wears an orange blouse, brown trousers, and black gloves. He also carried a cutlass during "La Resistance".
Though Gregory is portrayed as a smart and thoughtful young boy, he is also quite arrogant and looks down upon the other boys. This consequently causes Wendy to say to Stan at the end of the movie: "Fuck Gregory! Fuck him right in the ear!", meaning that she never liked him after all. It is also ironic of him being friends with The Mole, because of the British and French enmity within the show.
Gregory was briefly friends with Wendy in South Park: Bigger, Longer & Uncut. They shared the same liberal, political views. Their relationship was devoid of any romantic feelings, which Wendy clarified to Stan towards the end of the movie.
Although Gregory seems to take an instant disliking to the boys, because they are not very political, and can act rather childish at times, he is the one who points the boys towards "The Mole", so they can free Terrance and Phillip from Sheila's organization, Mothers Against Canada.
- Yardale is a portmanteau of "Yale" and "Harvard", two very known universities.
- Gregory is based on Enjolras from Les Misérables.