I recall reading an interview with Sydney where he claimed that he and Sammy Goldwin Jr were called the "bad boys" of BlackFoxe, the military school they attended.He claimed to have been kicked out of 3 schools by age 13, but records don't bear this out – he attended Black Foxe, then LawrenceVille Prep, then he quit that to transfer and attend Hollywood High instead of another boarding school.
Maybe part of his rebellion stemmed that unlike Charlie Jr. he wasn't in such awe of his father. Charlie Jr often said that Sydney was more daring of the two especially when it came to being disobedient towards Charlie Sr. What I always find interesting is how Sydney always talked about his dad in interviews and documenatries. Like Charlie Jr. he seems to remember really good moments but that bad ones he remembers with a reserve but a forgiveness especially in the later documentaries. I always found it interesting how the eldest Chaplin boys described Dad.
he dropped out of Lawrenceville prep after only one semester, or so he claims in his interview. He said he was in Hollywood High after that, and his mother Lita knew he was skipping out even there, because he would ask for lunch money and she'd say something like "what, a double feature today?". I need to find the interview links – they were all re-released after his death and quoted from in his obits.