Hard Eight (1996)
Philip Baker Hall as an aging gambler taking in a stranger. Released as Sydney against PTA's wishes.
Philip Baker Hall was in his sixties when Paul Thomas Anderson cast him in Hard Eight, having written the part for him after seeing him in a short film, and he appeared in three more of Anderson’s films.
Magnolia gives him a dying game show host, and Boogie Nights a small role of real sadness. Seinfeld gave him Lieutenant Bookman, a library investigator played entirely as a hardboiled detective, which is among that show’s best guest performances.