Woolf started as a playwright, penning comedies and farces (three of which boasted music by Jerome Kern). Among many other works, he wrote the 1906 review Mamzelle Champagne; at one performance, Harry K. Thaw murdered Stanford White.
Woolf and Florence Ryerson formed a screenwriting team in the 1930's; they wrote scripts for ten movies during that decade — largely forgotten works like The Ice Follies of 1939. They were called in to re-write Noel Langley's script for the Oz film on 3 June 1938.
Woolf was a talented cook, and fixed Sunday brunches for Louis B. Mayer and his guests. Woolf died in a freak accident, in which he tripped over his dog's leash and plunged down a flight of stairs.