When Robert De Niro saw Leonardo DiCaprio's acting in this movie, he called Martin Scorsese to tell him about the kid and he must check him out. Scorsese has since said that this was very unusual as De Niro wouldn't normally have this level of praise for a fellow actor.
Tobey Maguire first auditioned for the part of Toby but director Michael Caton-Jones thought he wasn't right for the role. Leonardo DiCaprio, who is close friends with Maguire, still wanted him to be a part of the film so he got him the role of Toby's friend Chuck Bolger.
Producer Art Linson knew the film would be a tough sell. When he attended a test screening of the film with the Warner execs, he asked an old lady what she thought of the film. To his delight, he found out that she loved the film. He later found out that the old lady was in fact Robert De Niro's grandmother.
The preparatory schools mentioned in the film all do exist. The Hill School is located in Pottstown, Pennsylvania, Choate Rosemary Hall is located in Wallingford, Connecticut, and Deerfield Academy is located in Deerfield, Massachusetts.
Leonardo DiCaprio mentioned the film during his acceptance speech at the 2016 SAG Awards. He also thanked director Michael Caton-Jones for casting him in his first film during his Oscar acceptance speech in 2016.