Hollingshead began his film career in 1916 as assistant director in the silent film era. In 1934 he received his first Oscar for best assistant director of the year. Subsequently, he began to work as a film producer. Until his death he produced a total of 174 films, including mainly short films. His last three short films have been published posthumously in 1953. He was nominated 16 times for an Academy Award six times, he received the award. At Hollingshead remembers a star on the Hollywood Walk of Fame, 6200 Hollywood Boulevard.
Hollingshead was the stepfather of the Norwegian actresses Tula Belle and Ebba Mona.