Chuck is a bit of a bully. He is frequently annoyed by Merton's attempts to be "one of the guys". He likes sports, including football and basketball. It is safe to assume he is privliged, because his father owns more than one Porsche.
Chuck gets a little physically rough with people, occasionally shoving Merton in annoyance or, as a werewolf, grasping Lori's wrist when he decided the date wasn't over yet.
He is pretty cocky and seems to have a penchant for stealing other guys' love interests, trying to get Hyacinthe to get with him instead of Merton and offering to take cheerleader Jenny to the pep rally when Tommy and Merton explain that Tommy can't go because he gets "moon freckles". He also enjoys the fact Tommy seems to be jealous of him and Lori being together in Dances Without Wolves.
Hyacinthe Thistlethorp is far from amused when Chuck asks her to "drop the zero, and get with the hero", casting a spell on him that renders him unable to speak for days. Jenny pushes him away from her when he puts an arm around her.
In the Chuck-iverse, he is the head quarterback for the football team and is dates Lori. Since the wish that brought the change in the world on was Tommy wishing he wasn't a werewolf, someone else had to get bitten instead. That person turns out to be Chuck. Merton never discovers Chuck is a werewolf when the changes start happening like he does with Tommy, though, and Chuck is still hostile toward him.
Chuck spends his time as the Pleasantville Werewolf stealing things, and is clearly not a good werewolf. At the end of his first fight with Tommy, Merton, and Lori, he bites Tommy and kills him, but the transformation brings Tommy back to life.
Werewolf Chuck reveals that he was always envious of Tommy's strong arm and speed on the football field before he got bitten. This indicates Tommy must have been a very good player, even without his powers of lycanthropy.
The actor who plays Chuck is James A. Woods.
- Pleasantville High Angry Badgers Football Team
Chuck Freeman is an interesting character name because Chuck is a name that is short for Charles, which is German for "free man". So he's "free man" Freeman.