He made his film directorial debut at age 34 with The Iron Cross (1914) and worked a number of times for Jules Greenbaum.

His pre-1920 efforts include such literary adaptations as The Picture of Dorian Gray (1917), Peer Gynt (1919), the once scandalous Different from the Others (1919) and Around the World in Eighty Days (1919).

[citation needed] He made a significant number of Operetta films during his career.

Being Jewish, Oswald was forced to flee Nazi Germany, first for occupied France and later emigrating to the United States.

His last production was The Lovable Cheat (1949), an inexpensive adaptation of a Balzac story which boasted a cast including Charles Ruggles, Alan Mowbray, and Buster Keaton.