In a career spanning 20 years, he appeared in films such as The Dark Past (1948), The Wild One (1953), I Bury the Living (1958) and Young Dillinger (1965).

Osterloh continued his career for 20 years, mainly in the 1950s, playing roles in films such as Illegal Entry (1949), White Heat (1949) (as a gangster killed by gang boss James Cagney), One Minute to Zero (1952), Star in the Dust (1956) and I Bury the Living (1958).

Filmed in 1956, "The Case of the Moth-Eaten Mink" aired in 1957 as the 13th episode of the legal drama series starring Raymond Burr; Osterloh played a central role as restaurant proprietor Morey Allen.

[4]: 10023  In "The Scarface Mob", the pilot for The Untouchables that aired on Westinghouse Desilu Playhouse in 1959, Osterloh was a member of the Federal squad led by Eliot Ness (Robert Stack).

Osterloh also played roles in TV series including Wagon Train, The FBI, Ironside and Hec Ramsey.