Occurring around the fifth season of the show, Rider Strong wanted to quit simply because he wanted to go to college. Michael Jacobs told him that they could work out a schedule so that he could go to college, and he did.
The episodes Prom-ises, Prom-ises (1998), If You Can't Be with the One You Love... (1998), and The Truth About Honesty (1999) were banned from airing on Disney Channel due to their frank discussion about pre-marital sex and teen drinking.
Rider Strong claimed that he loved the leather jacket he wore on the show so much that he didn't want to return it to Disney when the series was over. He took it with him to New York when he went to school, but it was stolen out of his car in Brooklyn. Instead of giving it back, he switched it out with another jacket.
The character of Topanga was originally just a fringe character, a kind of hippie new-age girl intended as a foil to the main characters. However, she proved so popular after her first few appearances that the producers expanded her character to become more mainstream and, eventually, a main player in the series and the love interest of Cory Matthews.
Despite having hundreds of kids sign up to audition for the part of Shawn, Rider Strong was the first, and last, actor that producer Michael Jacobs saw.