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.
He must not have attended Hollywood High very long because I believe he dropped out of school after the 8th grade. I think he was the more rebellious one though (before Michael came along). I remember Sydney saying once that when his father died he left his fortune to Oona because he knew Sydney would just fritter away any inherited money.
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.
I'd like to read that interview if you can find it. He also mentions that story in his forward to Lita's book "Wife Of The Life Of The Party." I don't think Sydney did too many interviews because he evidently wanted an outrageous amount of money for them. Here is an article he wrote for People back in 1989. He has some interesting things to say about Barbra Streisand and Claire Bloom.http://www.people.com/people/article/0,,20119829,00.html